Vacation Home Rentals By Owner In Orleans, MA

$1037.78

Spacious Skaket Beach Retreat

Orleans, Massachusetts, United States

Beautiful custom 4 bedroom 3.5 bath home with high end finishes throughout is just .4 miles up the street from Skaket Beach.brEnjoy central AC, a large kitchen with leathered granite counters, stainless appliances and gas cooking as youbrgather with family and friends. Large dining space in kitchen and huge living/dining room is adjacent. Hardwood floors throughout the main level. Four large bedrooms and three full baths on upper level. Laundry room is also on upper level. brbrNo Pets

4

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3

Bath

8

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$393.59

/ Nightly

Private Vacation Home

New 2026 Beautifully Curated Orleans Retreat Close to Beaches, Trails, and Golf

Orleans, Massachusetts, United States

Summary:brbr3/4 mile from Pahwah Landing for kayaking on Little Pleasant Bay. Relax with a grassy yard, patio and deck spaces, and flexible gathering areas.brbrbrbrThe Space:brbrWelcome to Love & Luck, a breathtaking, well-maintained vacation retreat in South Orleans. This spacious, magazine-worthy home offers multiple living spaces both inside and out, ideal for multi-generational gatherings. Thoughtfully designed with curated details and abundant natural light, it provides a sanctuary for relaxation and a place to reconnect with loved ones. Just ¾ mile from Pahwah Landing, you’re within easy reach of kayaking on Little Pleasant Bay, while a peaceful, family-friendly neighborhood keeps you close to nature without sacrificing convenience. Skaket Beach, Nauset Beach, and downtown Orleans—with its dining, shopping, and summer baseball at Firebirds Field—are all only a short drive away.brbrbrbrArriving at the property, you will be immediately struck by its curb appeal, with a manicured lawn and well-kept gardens. Step inside to a functional mudroom with plenty of hooks and space to kick off sandy flip-flops, then move into the bright, sunlit kitchen featuring a skylight, modern stainless steel appliances, double ovens, and an eat-in island perfect for family meals. A washer and dryer tucked into the kitchen closet add convenience for longer stays. The home offers multiple gathering spaces, including an intimate formal dining room, a casual dining area in the living room, a separate TV room with vaulted ceilings, and intimate conversation nooks. With mini-split A/C and a dedicated workspace, the house stays comfortable and adaptable for multi-generational trips or two families traveling together. Outside, the property comes alive with a large grassy yard, inviting patio, and decks for lounging, morning coffee, or evening cocktails. Roast s’mores around the fire pit, take an outdoor shower after a day at the beach, or fire up the pizza oven for casual summer meals.brbrbrbrLove and Luck provides easy access to the very best of Cape Cod. Spend the day at nearby Skaket or Nauset Beaches, paddleboard or kayak on Little Pleasant Bay, or explore walking trails through surrounding conservation lands. Rent bikes and ride along the Cape Cod Rail Trail, or visit Orleans and Chatham centers for boutique shopping, local dining, and live summer entertainment. Families will love catching a Firebirds baseball game, while golf enthusiasts can enjoy Wequassett Resort and Golf Club, just minutes away, with its world-class courses and fine dining options. With so many experiences and adventures within easy reach, this thoughtfully curated retreat is the ideal home base for making lasting Cape Cod memories.brbrbrbr**Linens and bath towels are provided. Please remember to bring your own beach towels!** brbr**This is a dog friendly home. If you plan to bring your dog, please inform Nauset Rental so we can send you screening questions.**brbrbrbrLayout of Bedrooms & Bathrooms:brbrbrbrMain LevelbrbrBedroom #1 - Primary bedroom with a king bedbrbrbrbrBathroom #1 - Primary ensuite with a tub and showerbrbrBathroom #2 - Half bathroombrbrbrbrUpper Level brbrBedroom #2 - Queen bed and a twin bedbrbrBedroom #3- Queen bed and a twin bed brbrbrbrBathroom #3 - Full bathroom with a tub and showerbrbrbrbrOther Things to Note:brbr-

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Bath

Sleeps

$315.03

/ Nightly

Private Vacation Home

Dream Waterfront A-Frame in Orleans!

Orleans, Massachusetts, United States

Summary:brbr15544 - Sunset Chalet: Dream Waterfront A-Frame in Orleans!brbrbrbrThe Space:brbrWalking up to this beautiful waterfront A-frame home, you really can’t help but smile; the home is so cute, but also angular and solid, and really is just a sight to see perched directly in front of the pond. The ground level deck stretches the home even closer to the water, and the perfectly manicured lawn leading down really makes the outdoor space feel like an oasis. A gas grill enables you to cook an amazing waterfront meal, and a full kitchen inside will assist in any additional cooking needs (Note: fireplace not for guest use). Eat out on the deck, or, dine with the family or friends at the table inside, where you’ll still have unobstructed views. The main area of the home is open, bright, and inviting, with a living area to the left, an eat-in kitchen behind, and dining to the left. Further back on the first floor, there is a bunk room with a single twin and trundle, and a bunk bed. This rooms sleeps 4 comfortably and a fun round porthole skylight captures the nautical feel of this home. At the rear of the A-frame, a small seating area and bathroom are just before sliding doors that lead to a small rear deck with an outdoor shower. Upstairs, you’ll find an amazing master suite that will have you feeling like you’re living in a treehouse, or on the bow of a ship. The master bedroom offers a queen bed, plus a en suite half bathroom, as well as its own private balcony on the rear of the home. Just outside the bedroom door is a small seating area with a single Adirondack, which has sweeping views of both inside and outside; a great place to sit and read, or just daydream.brbrWhen it comes time to leave your oasis in search of food or activities, you’ll be pleased to find that Main Street in East Orleans is just under a mile away, and offers several restaurants and grocery shopping at Nauset Farms. If your body is craving saltwater and sun, Nauset Beach is just two miles away, and is perhaps one of the best beaches on Cape Cod. Downtown Orleans sits just two miles away, and has great dining options, shopping, and if you continue toward the bayside, you can catch unbelievable sunsets at Rock Harbor, and Skaket Beach. This home truly is an escape to Cape Cod and is a unique experience plus an ideal location that is a recipe for an unforgettable vacation!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 6br-2 Floorsbr-2nd Floor Bedroom: 1 Queen Bed w/ en suite Half Bathroombr-1st Floor Bedroom: 4 Twin Beds (bunk bed + single w/ trundle)br-Split A/C Units br-WiFibr-Cable TVbr-Washer/Dryer br-Gas Grillbr-Fire Pitbr-Deck w/ Furniturebr-Outdoor Showerbr-Private Yardbr-Waterfront on Uncle Harveys Pondbr-Direct Water Access From Propertybr-Cleaned With Hospital Grade Disinfectantbr-Sheets and Bath Towels Provided With Beds Made Upon ArrivalbrC0410132240brbrbrbrThe Neighborhood:brbrOceanside

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$665.59

/ Nightly

Private Vacation Home

Peaceful Cape Cod retreat, 1.5mi to National Seashore

Orleans, Massachusetts, United States

Beautiful and private setting with easy access to all that the outer cape has to offer! The living/dining room opens up through double sliding doors onto a multilevel deck and natural landscaped gardens and yard rolling down to wetland. Three spacious bedrooms including king master suite are on the main level. Additional living space downstairs include game room with pool table and home theater, and playroom with additional sleeping space. Multiple living spaces make this house perfect for family gatherings. The house is equipped with high speed internet and desks in living room and master suite for telecommuting needs. It's a short stroll to water views and access to Pleasant Bay, under 2 miles to beautiful Nauset beach on the National Seashore, and 3 miles to Orleans Main St with shopping, art galleries, restaurants, and the Cape Cod Rail bike trail.

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Sleeps

$413.04

/ Nightly

Private Vacation Home

Walk to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15521 - Nauset Beach Bungalow: Walk to Nauset Beach!brbrbrbrThe Space:brbrOur classic Cape cottage is the perfect place to bring family or friends for your next getaway to the Lower Cape. Within walking distance to famous Nauset Beach, this cute Cape Cod beach house will serve as a great home base for you while discovering all of what the Cape has to offer. Return from a day at the beach, take an outdoor shower, and throw some burgers on the grill for a nice meal outside on the private deck. Take a stroll down to Smitty's after dinner for some delicious homemade ice cream, and return back to relax comfortably with the family in the air conditioned cottage. Such an amazing location, with all the amenities you will need, make this rental the ideal choice for your next Cape Cod vacation! Also - For larger groups, rent our other condo in the adjacent building! 15505 Beach Rose br brHome Details: br-Sleeps 4 br-1 Floor br-Master Bedroom: Queen Bed br-Bedroom #2: 2 Twin Beds br-Split A/C br-Cable TV br-WiFi br-No Pets br-Outdoor Shower br-Private Deck br-Gas Grill br-Minutes From Nauset Beach br-Sheets and Bath Towels Provided with Beds Made Upon Arrival br-Cleaned with Hospital Grade DisinfectantbrC0418072240brbrbrbrThe Neighborhood:brbrOceanside

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Sleeps

$690.44

/ Nightly

Private Vacation Home

Escape and Relax in this East Orleans home with magnificent in-ground heated pool

Orleans, Massachusetts, United States

Summary:brbrFreshly painted quiet retreat with pool and central A/C close to Nauset Beach, restaurants and morebrbrbrbrThe Space:brbrThis well appointed home, is situated on a quiet lane yet centrally located to several bodies of water for swimming, boating, fishing, as well as all of the activities, restaurants and entertainment that Orleans has to offer. Complete with a private backyard and heated pool, this home has all the makings for a wonderful Cape Cod vacation. brbrbrbrEntering through the front door you are welcomed into a spacious, updated living room. There is plenty of comfortable seating around the television for relaxing with your family at the end of a fun filled day. You can host a wonderful dinner for your family and friends in the well-equipped kitchen, and be few short steps away from the bright dining room to gather around the table. Wash the day away in the full, remodeled bathroom with tub and shower on the main level of this home. brbrbrbrWandering upstairs, you will be met with the four bedrooms. brbrThe primary queen bedroom has ample closet space for all of your belongings, and plenty of natural light for you to wake up to during the summer. The second queen room is decorated nicely and is a cozy room to drift off in. brbrEven if you don't need all four rooms, the third and fourth bedroom have plenty of space to make for a great quiet space to read, write, or just enjoy the company of the people around you. This floor also has a bathroom with a shower and stunning vanity with plenty of drawers for all of your vacation must haves! brbrbrbrThe backyard will make for the perfect relaxation zone. Host a number of cookouts for your family with the comfortable patio seating thoughtfully placed next to a grill- perfect for any bbq lovers in your group! There is also a beautiful heated, in-ground pool with its surrounding patio. Lounge beside the pool catching some rays, or cool down by taking a dive! The yard is large and flat to play all of the summer games both old and new. brbrbrbrStay at home and relax or head to the beaches, attractions or restaurants, either way you'll have a wonderful time in the home, and in the great area this home is located. brbrbrbr**Pool opens for the season on 6/1**brbrbrbrLayout of Bedrooms & Bathrooms: brbrMain LevelbrbrFull bath with tub/shower combo brbrbrbrSecond LevelbrbrBedroom 1 - QueenbrbrBedroom 2 - QueenbrbrBedroom 3 - Twin Bunk and Twin w/TrundlebrbrBedroom 4 - Full Size Sleep SofabrbrFull bath with showerbrbrbrbr**Linens are included**brbrbrbrGuest Access:brbrThe whole space.brbrbrbrOther Things to Note:brbr-

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$658.09

/ Nightly

Private Vacation Home

Close To World Class Beaches And Village

Orleans, Massachusetts, United States

Sprawling 5 Bedroom Vacation Home Sleeps 12, Pet Friendly. Squeaky clean listing close to beaches, town, and bike path. Centrally air conditioned and freshly decorated in colorful light-hearted tones, it's sure to appeal to your gang. The tavern table plus kitchen island provide combined seating for 15… or step out to the sprawling wraparound deck via 3 sets of sliders and enjoy your meals al fresco. Well-equipped gas grille perfect for the “catch of the day” or kid-pleasing burgers. Two generous awnings provide shelter on the deck while still leaving open space for sun-worshippers. Lots of deck furniture. The level yard offers plenty of room to toss a Frisbee. Great outdoor shower for getting rid of the beach sand. The first floor Master with four-poster bed will remind you of a fine New England B & B, generous first floor bathroom with tub and shower; adjoining laundry offers full size washer and dryer, The corner living room is decked out in red, white and blue with comfortable furnishings for watching your favorite show on TV or curling up with a good book. The second level has four corner bedrooms, large bathroom offers tub and shower; plus a multi-purpose den/game room/office where in addition to games, puzzles and books, there is even a desk with comfortable chair for the person who isn't completely on vacation. Our favorite, the whimsical BFF room offers a set of bunk beds plus a trundle... 4 twins in all, dressed in crisp turquoise stripes is perfect for the younger members of your group. Enjoy easy access to Nauset beach, Orleans center, Chatham village, Pleasant Bay, Bay beaches, Crystal Lake and the bike trail from this great location.brPlease note that bed linens and bath towels are not provided. You will need to bring these on your own. I can recommend a linen service for you if needed. The only reason I mention this is there has been some confusion concerning this with previous guests.

5

Bed

2

Bath

12

Sleeps

$1226.86

/ Nightly

Private Vacation Home

Skaket Beach Area Dream

Orleans, Massachusetts, United States

SPECIAL PROPERTY NEAR SKAKET BEACH within a half mile from private association path access to the beach. New to the market, this bright and beautiful, beach themed home offers everything for an unforgettable vacation.brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrEnter the front door to find an incredible open floor layout with expansive gourmet kitchen with large center island, dining area and living room. There is a separate family room, full bathroom with shower, laundry closet with washer and dryer, and two bedrooms; one with a twin bed and twin trundle under, and the other bedroom with a queen bed. brbrThe second floor boasts a spacious master bedroom with a king bed and a separate office space for those who may bring work along, and includes a nice master bathroom with built in bathtub and separate walk-in shower. The fourth bedroom is across the hall and offers one queen bed and one twin bed. There is a full bathroom with tub next to this bedroom.brbrThe grounds are nicely landscaped with a lush grassy and completely fenced-in backyard. There is a large wrap around deck with retractable awning on one side and a dining area on the shady side. Also, there is an enclosed outdoor shower and shed which holds 2 paddleboards and tennis rackets for your use.brbrLocation: This house is located .4 mile from private bayside beach path at the end of Willie Atwood Road, and .6 mile to the Skaket Beach Parking Lot. It is only .9 mile to the Bike Trail and 1.6 miles to Orleans Center. Nauset Beach on the oceanside is 4.7 miles away and if you like to swim in a freshwater pond, Crystal Lake is just 3.4 miles away.brbrAmenities: central air conditioning, 1 gig internet access, 2 - 50 Smart TVs with Roku streaming and 1 - 32 monitor hookup for laptops, 1st floor washer and dryer, dishwasher, electric range, microwave, drip coffee maker, french press, electric tea kettle, gas grill, 6 beach chairs. hammock. Sheets and towels are provided.brbr* Additional Fees:br- $200 Non-refundable Pet Deposit plus a Refundable $200 Pet Security Depositbr- $220 Non-Refundable Reservation Fee; $30 Damage Protection Fee; Guest Services Feebr- All Applicable Taxesbr* FREE WIFIbr* SUNDAY TO SUNDAY RENTALbr*A WELL-BEHAVED DOG MAY BE CONSIDERED UPON OWNERS APPROVALbr* NO SMOKINGbr* OCCUPANCY: 9 (adults and children)br* PARKING FOR 4 VEHICLESbr* Sheets and Towels Providedbrbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change. Not available on stays over 28 days.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC OBARO

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Select Dates for Price

Private Vacation Home

Spacious deck with amazing view, neighborhood path to Skaket Beach, game room

Orleans, Massachusetts, United States

The expansive deck with amazing views is great for bringing everyone together for meals, entertainment, sunset and evening firepit. brThe open floor plan of this contemporary home with picture worthy views has been designed with family and friends in mind. brbrThe 4 large bedrooms sleep 10 in beds and all have special features. The 2 upstairs bedrooms both have incredible views and they each have a workstation. The first floor bedroom has a gas fireplace, one of 3 gas fireplaces in the home. The garden level has been completely renovated in the spring of 2022 and has a beautiful new bathroom. brThis home has 3 full bathrooms and an outdoor shower. brInstant fun and entertainment anytime in the gameroom with the brand new ping pong table. The garden level walks out to backyard and has large completely renovated tv ares (tv not in picture). In cooler months enjoy snuggling up next to the 3 gas fireplaces: located in livingroom, game room and 1st floor bedroom.brThis is a gorgeous home with a fantastic location. brJust .4 miles to neighborhood path to private area of Skaket Beach. brClose to the Cape Cod Rail Trail bike path. brWhen you're here you feel so far away with the convenience of fantastic shops and restaurants and everything this area has to broffer right down the street in Orleans center.brOur home is a great place to work from as we have we have 3 desks with super fast internet.

Bed

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Sleeps

$728.24

/ Nightly

Private Vacation Home

Steps to Skaket Beach!

Orleans, Massachusetts, United States

Summary:brbr15563 - Bliss by the Bay: Steps to Skaket Beach!brbrbrbrThe Space:brbrSandy beaches, sunshine and sunsets are waiting for you at Skaket Beach. And with the summer sand less than 500 feet from your front door, you’ll be feeling nothing this vacation except Bliss by the Bay. br br Pulling into the roundabout driveway, greenery and foliage surround the home, giving privacy and calmness the second you arrive. Walk down the winding pebble path by the beautiful front lawn, up onto the covered front porch, where afternoon drinks can be enjoyed on the outdoor lounging options under the shade of the porch. Opening the navy blue door, you’re welcomed into the home’s formal living room, a stunning room flooded with natural light from the skylight above, as well as the windows and patio door overlooking the backyard and cobblestone patio. Staying downstairs, enter into the sprawling kitchen, with rich wood cabinetry, large center island with Vulcan stove, and plenty of counter space. Once your vacation meal has been made, head into the dining room to enjoy your feast, or sit in the adjacent den where beautiful midday light pours in through the windows.br brStepping off the dining room, three of the home’s four bedrooms can be found. To the right is a bedroom with a queen size bed and large windows overlooking the front garden. To the left is another bedroom with a full size bed and stylish artwork on the walls. Stepping off of this bedroom is the final first floor bedroom, complete with two twin beds and massive windows on the back wall. Please note, access to the bedroom with two twin beds is through the bedroom with the full sized bed. brbrHeading upstairs from the formal living room, your jaw will drop upon entering the upstairs of this home. An entertainment room awaits, with vaulted ceilings, TV and numerous seating areas, as well as natural light flooding in from the two large skylights, panoramic windows and patio door leading out to the second floor balcony/deck. brbrLocated past the entertainment room is the home’s primary bedroom, the final bedroom in this sleeps 8 home. This spacious room with vaulted ceilings, access to private back deck, and four post bed has a large en suite bathroom, complete with jacuzzi tub, glass shower and towering ceilings.brbrOutdoors, the beauty of this two story home continues, with a lot so private that you forget you are less than 500 feet from Skaket Beach. The backyard provides room for yard games, while the patio welcomes you for evening cocktails and outdoor meals at the outdoor dining table. brbrOther amenities include a washer and dryer, propane grill and an outdoor shower. Artwork throughout the home gives a tasteful, artistic vibe, while the home’s prime location reminds you how truly special vacationing to Cape Cod can be. Countless beaches, delicious food, and more can be found in the beauty of Orleans, this vacation you will be feeling pure Bliss by the Bay.brbrHome Details:br-Sleeps 8br-2 Floors br-3,223 Sq FtbrBedroomsbr-Total 4br-Bedroom #1: 1 Queen Bed w/ en suite Full Bathroom, 2nd Floorbr-Bedroom #2: 1 Queen Bed, 1st Floorbr-Bedroom #3: 1 Full Bed, 1st Floorbr-Bedroom #4: 2 Twin Beds, 1st FloorbrBathroomsbr-Total 2br-Bathroom #1: Full Bath w/ Shower and Jacuzzi Tub, en suite, 2nd Floorbr-Bathroom #2: Full Bath w/ Shower, 1st Floorbr-Fully Equipped Kitchen w/ Islandbr-Vaulted Ceilings w/ Skylightsbr-Mini Split A/C Unitsbr-Smart Lock/Self Check-Inbr-WiFibr-Smart TV w/ Cablebr-Washer/Dryer (1st floor)br-Patio w/ Outdoor Diningbr-Propane Grillbr-Outdoor Showerbr-Private Yardbr-NO Pets (fines remitted)br-Steps to Skaket Beach (500 ft)br-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0406272240brbrbrbrThe Neighborhood:brbrBayside

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$432.17

/ Nightly

Private Vacation Home

Pristine Cottage: EV charger, AC, outdoor shower+ firepit, walk to Bakers Pond

Orleans, Massachusetts, United States

Welcome to Joy Cottage! Our Cozy Cape Cod cottage is tucked away in the woods, within walking distance to Bakers Pond in Orleans, MA and boarders Nickerson State Park. The cottage is 4.5 miles from Nauset Beach and 2 miles from Skaket Beach. brbrJoy Cottage features a large wrap-around deck and a roomy outdoor shower. The cottage shares a spacious, well landscaped yard with the owners residence. During the prime summer weeks, the owners residence is also rented out to vacationers. The cottage also has its own personal backyard space with plenty of privacy and fire pit. Level II EV charger on the property for guest use.brbrUpstairs: The kitchen has a gas stove with above microwave, dishwasher, and refrigerator. Queen size bedroom and one full bathroom is located on the main floor next to the kitchen and dining area. A spiral staircase takes you down stairs to where the second bedroom (twin bed) and living area (queen sleep sofa) are located with a walk out entrance. Two wall mounted AC units, private laundry, fire pit, beach supplies: cooler, umbrella and chairs, and WiFi included.brbrWe offer contact-free, keyless entry for each guest (all of the doors are electronic keypads). Please note the spiral staircase might not be suitable for all guests. Ideal for a couple, 3-4 friends, or a couple with one or two small children.

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$403.2

/ Nightly

Private Vacation Home

The Perfect Beach Getaway!

Orleans, Massachusetts, United States

Summary:brbr15534 - The Bunny Patch: The Perfect Beach Getaway!brbrbrbrThe Space:brbrOur cheerful and impeccably clean home is located in desirable East Orleans, near to famous Nauset Beach and other great Outer Cape attractions. Your Master bedroom will be spacious, with a Queen bed and en-suite full bathroom. The two other bedrooms each have two Twin beds and share a full bathroom. Our kitchen is large and updated, perfect for whipping up family favorites, and we also have two separate living areas and dining area as well. The house is all on one level, so there are no steep stairs to contend with. Spend your day soaking up sunshine at the beach, taking a seal tour out of Chatham, shopping the boutiques, cruising the bike trail or day tripping to Provincetown. Return home to grill up some summertime favorites while the children and family dog play in the large backyard. Spend the evening at a fun Cape Cod Baseball League game or lively band concert. Everything needed for a comfortable, fun and memorable Cape vacation will be found at our sweet home.br br brHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 6br-Single Level Homebr-1st Floor Master Bedroom: 1 Queen Bedbr-1st Floor Bedroom #2: 2 Twin Bedsbr-1st Floor Bedroom #3: 2 Twin Bedsbr-A/C units in bedroomsbr-Cable TVbr-WiFibr-Washer/Dryerbr-Outdoor shower br-Gas Grillbr-Walk to Waterbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0432992240brbrbrbrThe Neighborhood:brbrOceanside

3

Bed

2

Bath

6

Sleeps

$658.33

/ Nightly

Private Vacation Home

Walk to Nauset Beach

Orleans, Massachusetts, United States

Summary:brbrRelax on the spacious deck, rise off the sand in the outdoor shower, and unwind with a collection of books and games in this ultimate summer retreat.brbrbrbrThe Space:brbrWelcome to Nauset Winds, a charming Cape Cod beachhouse tucked away on a sleepy dirt road in the highly sought after neighborhood of Nauset Heights in Orleans. This home hearkens back to a simpler time, where the smell of the salt in the air and the faint rumbling of the ocean tides in the distance imbue a sense of calm and set the stage for a truly tranquil beach vacation. Just over a quarter mile from your front doorstep, you will find yourself with your toes in the pristine sands of Nauset Beach, overlooking dramatic vistas of the Atlantic Ocean, rambling dunes, and reveling beachgoers. brbrbrbrWhen you pull up the driveway and around to the back of the house, you’ll be greeted by a gorgeous new back deck. It’s the perfect spot to soak up the sunshine, surrounded by whispering pitch pines. Inside, the charming kitchen is fully stocked with everything a discerning home chef might need (lobster pot included!). The kitchen features an intimate dining table, perfect for a quick breakfast before heading to the beach or enjoying a game of cards in the evenings. From here, you can look into the living room, which is a true showstopper. With dramatic cathedral ceilings, new furnishings, and bright pops of navy and yellow, this space gives the home its soul—making it an ideal gathering spot for family and friends. The living room also offers a great selection of books and games, and a TV for movie night. The three cozy bedrooms each have their own charm, with plenty of books to choose from as well. The main level includes the primary bedroom with a queen bed and a second bedroom with two twins. The entire lower level is a spacious third bedroom, featuring a twin bed, a twin trundle, and a queen bed.brbrbrbrNauset Winds is ideally located to take full advantage of all that Orleans and the surrounding area have to offer. Just a short drive away, you’ll find fantastic local restaurants like The Rail and The Barley Neck Inn, perfect for savoring fresh, local seafood and Cape Cod fare. For those who enjoy cooking at home, Nauset Farms offers a fantastic selection of meats, fresh produce, and prepared foods, making it easy to bring the taste of Cape Cod to your kitchen. And for a little culture, don’t miss a visit to the Academy Playhouse, where you can enjoy live theater and a taste of local arts. Whether you’re exploring the outdoors, dining at local favorites, or taking in the arts, you’ll find everything you need to make your stay at Nauset Winds truly memorable.brbrbrbrLayout of Bedrooms & Bathrooms brbrbrbrMain Level brbrBedroom #1 - Queen bed brbrBedroom #2 - Two twin beds brbrBathroom #1 - Full bathroom with a tub and shower brbrbrbrLower Level brbrBedroom #3 - Queen bed, twin trundle bed, and twin bed brbrBathroom #2 - Full bathroom with a tub and showerbrbrbrbr**Linens and bath towels are included.** brbr**This is a pet friendly home. Please inform Nauset Rental if you plan to bring your dog along so we can gather some information for our records.**brbrbrbrOther Things to Note:brbr-

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$956.31

/ Nightly

Private Vacation Home

Crystal Lake Waterfront Haven

Orleans, Massachusetts, United States

This beautiful 3 bedroom 2.5 bathroom Crystal Lake home has high end finishes throughout and a location that brcan't be beat! Crystal Lake Haven has peeks of Crystal Lake and direct access to the lake via the property in front of it. The main level offers a large eat in kitchen/living area with a gourmet kitchen with an island, a large family room, and a dining room with access to the large deck. From the deck you can see peeks of Crystal Lake. The main level also offers the primary bedroom, complete with a king bed, and a full en-suite bathroom. A half bathroom is also on the first floor. The second bedroom with a queen bed and twin bunk beds is on the upper level as is bedroom #3 with a king bed. The two upper level bedrooms share the second full bathroom. Streaming smart tvs.brFeel like a day on the ocean or bay Nauset and Skaket Beaches are just a short drive away. brbr Having a large family vacation Rent the second property on this lot as well (DIX1ORL).

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$1728.77

/ Nightly

Private Vacation Home

Nauset Beach Retreat! Pool w/Spa & Gas Fire Pit

Orleans, Massachusetts, United States

Smell the sea air and listen to the soothing rhythm of the ocean at Sea Mist! A short 2/10ths of a mile from one of the most beautiful beaches on Cape Cod, this property brings together easy access to Nauset Beach with the luxury of a salt-water heated pool that includes a hot tub and sun shelf. Inside, the four bedroom house combines a quiet elegance with a cozy, beach house feel. On the first floor there is an airy ensuite queen bedroom with a double sink in the beautifully tiled primary bath. The large second bedroom has space for a private sitting area with a queen-size couch that converts to a second queen bed when extra sleeping space is needed. All the bedrooms include a desk where electronics can recharge or be put to use. Upstairs, a spacious king bedroom offers glimpses of the ocean and an alcove that holds a trundle bed with two twin mattresses. The room can easily accommodate a family of four or a kids sleepover! The fourth queen bedroom overlooks the pool and gardens and shares a stunning, remodeled bathroom with separate sinks and sea glass tile accents.brOn the main floor, the updated, fully-equipped kitchen includes a coffee bar (complete with a Keurig), ample work space, and high-quality appliances to make feeding your crew easy and enjoyable. Flip pancakes onto waiting plates at the gas-range island or gather around the large dining table in your banquet eat-in kitchen area. For special occasions tables can be arranged in the library for luxurious dining, with a gas fireplace bordered by built-ins adding to the charm. When not being used for dining, the library is a welcoming, cheery place for family game night, working on puzzles, and finding the perfect beach read. A second gas fireplace warms your evenings in the family room, where a 60-inch TV supports family movie nights or gaming sessions. In daylight, the high ceilings and generous transom windows make this room a perfect spot for sinking into a couch or chair with a good book and a nap on the horizon. If you prefer to dine and unwind outside, the sunroom and back deck are great options. Grill and crack lobster shells poolside on the deck, or steal away for some quite time in the serenity of the screened-in sunroom. The wooded conservation land next door provides added privacy to the beautifully landscaped grounds. The back yard is bounded on one side by a secret garden where children can play in outdoor bliss and everyone can find a quiet nook for reading and relaxing among the trees. The grassy lawn at the front can serve as a platform for badminton, corn hole or flashlight tag. Combining lovely spaces with fun features makes Sea Mist the perfect place for building life-long memories!brAll Linens are included.brLarge shed that locks is perfect for bike storage! Shed is stocked with a beach cart, pool toys, beach toys and beach towels!

4

Bed

2

Bath

10

Sleeps

$442.9

/ Nightly

Private Vacation Home

Long View Cottage Close to Nauset, Skaket, & Bakers Pond

Orleans, Massachusetts, United States

JUST LISTED - JUST IN TIME FOR SUMMER!brbrThe beautifully updated home can sleep up to 9 people with the finished lower level walk out basement. This home is located 1.4 miles from the center of Orleans, 4.3 miles to Nauset Beach, and just over 2 miles to Skaket Beach.brbrThere is a nice covered porch in the front of the house and a patio in the back with a dining table and gas grill for enjoying a pleasant summer BBQ. brbrEnter to find an incredible open living room with vaulted ceilings, dining area and a fully equipped kitchen. This home is light and bright with beautiful updates throughout. This ranch style house also offers a full bath with combination tub and shower, a master bedroom with ensuite half bath, and a second bedroom with a bunk bed set with a double bed on the bottom and twin on top.brbrThe lower level is partially finished with a spacious room with seating and one queen bed and one double bed. The washer and dryer is located in the unfinished part of the lower level.brbrAmenities include: Ductless air conditioning in the great room and window units in the upstairs bedrooms, WiFi, large flat screen TV with soundbar, new gas stove, dishwasher, microwave, drip coffee maker, outdoor dining set, gas grill and an enclosed outdoor shower.brbr* Additional fees: $220 non-refundable reservation fee; $30 damage protection fee; guest services fee; all applicable taxesbrbr* SATURDAY TO SATURDAY RENTALbr* SHORTER STAYS AVAILABLE, THREE-NIGHT MINIMUM, LESS THAN 7 DAYS, $200 CLEANING FEEbr APPLIESbr* NO SMOKINGbr* NO PETSbr* FREE WIFI br* OCCUPANCY: 9 PEOPLE TOTAL (adults and children)br* PARKING FOR 3 VEHICLESbr* SHEETS AND TOWELS ARE PROVIDED FOR YOUR CONVENIENCEbrbr* CONSIDER RENTING 32 OR MORE DAYS AND TAXES WILL BE ELIMINATEDbrbr****FREE INCLUDED ACTIVITIES****brTo enhance your vacation experience, eligible* Kinlin Grover Compass rentals include access to our exclusive XPLORIE program!brThis virtual activities concierge will assist you in accessing a variety of complimentary activity tickets for select popular attractions in the area.brCurrent offerings include: Ferry tickets to the islands, whale watches, golf tee times, mini-golf, the Pirate Museum, ice cream, kayak tours, bike rentals and more!brOne free ticket per reservation, per day for every activity.br(*eligible for stays shorter than 28 days only)brbrbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.

Bed

Bath

Sleeps

$322.46

/ Nightly

Private Vacation Home

A Change of Pace: Relaxing Orleans Getaway

Orleans, Massachusetts, United States

2 Bedroom - 1.5 Bathrooms - Sleeps 4brA 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details.brGuests can bring their own linens or rent from our Linen Service for an extra fee (Bed Sheets and Pillowcases, Bath, Beach, and Kitchen Towels)brWe offer a 4 pm Check-In and 10 am Check-OutbrbrA Change of Pace is exactly what you will get when staying at this Orleans home. Unique decor and artwork reflecting the family's interests and tastes, minimal clutter to help with the chill vibe you are looking for in a Cape Cod retreat and an overall feeling of being one with nature while hanging out in the large backyard will be the amenities you talk about when fondly remembering your stay at A Change of Pace. One floor living, sleeping four, pet friendly, and wheelchair accessibility round out the offerings at this lovely cottage just a short drive to Skaket Beach.brbrLet Us Tell You About This Home:brAs you drive up to A Change of Pace, the hydrangeas and other local flowers greet you. This home has some added features for our handi-capable guests like the ramp leading to the front door.brbrYou get a sense of the style of this home once you cross the hearth and experience the overall feel that is representative of the owners with the comfort of their guests top of mind. One level living, this home offers ease of movement throughout. There are mini-split A/C units in each bedroom and the main living areas. There are also ceiling fans for those nights when the cool breezes are blowing.brbrThe living room is simple yet relaxing with classic furniture from decades gone by mixed with unique artwork and colors pleasing to the eye. The natural plants throughout the home help make the connection from the inside decor to the serene outdoors. They didn't forget the amenities you want on vacation - large screen TV for catching a summer baseball game and comfy furniture to enjoy late night catch up sessions with your friends and family.brbrThe kitchen and dining room are open to each other and accessible from the living room. The kitchen has all the features you'd expect including a dishwasher. The center island is a great place to hang out and help the cook in your group prepare the meals for your stay. Lots of cabinets and counterspace make the preparation a breeze.brbrThe dining area seating is open to the kitchen and creates and easy pathway from stove to table. You can also access the all season room from the kitchen. This room can be whatever you would like it to be - it has a desk for remote working, a couch for laying around on a rainy day and reading trashy beach novels and additional seating if you want to eat with a view of the backyard.brbrThe hallway to the two bedrooms has a full bathroom with glass enclosed shower and safety grab bars. Bedroom #1 with walls the color of a perfect cloudless sky, has a queen bed and an ensuite half bathroom for your convenience. Bedroom #2 with two twin beds invokes the feeling of bringing the outside inside with its live plants and jungle decor.brbrThe back deck is accessible through the all season room. A gas grill for grilling burgers while the dogs play in the large backyard. Yes, your furry family members are invited, too! There's a small bistro table and chairs for afternoon cocktails as the sun starts to set. Don't forget the enclosed outdoor shower with hot and cold water - a Cape Cod tradition!brbrCome stay and play, relax and chill at a Change of Pace in Orleans!brbrFree Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you're not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun.brbrWith all NEVR properties, we think of the little things to make your vacation special. Our Guest Welcome Bag, compliments of the homeowner, contains starter quantities of kitchen and bathroom essentials, with a few locally sourced snacks as well (subject to change based marketplace availability).brThis home has Keyless Entry for your convenience.brNO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brDOG FRIENDLY HOMES are for a DOG only. This home allows 1 dog for $25 per night. With owner approval, a second dog may be considered for an additional $25 nightly fee. A Pet Registration form must be completed upon reservation confirmation. brMax parking of cars at property: 3 - No parking on the lawn anytime. brFireplace is not available for guest use.brWasher/dryer available for use brbrAdditional Information to Assist You:brFollow our basic check-out instructions at your departure for no additional cleaning charges.brState and local taxes are charged if applicable. brFor Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments.brA confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. br***Linens - bed sheets, bath/dish/beach towels and bath mats are not included with this home but can be rented at time of booking or at a later date through our linen rental partner. Please ask our guest specialist for details. Our NEVR Homes come with mattress covers, pillows and a bed cover such as blanket, quilt, bedspread etc.brYou must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. brbrArea Info: *Mileage is approximatebr1.2 miles to Skaket Beachbr1.4 miles to Town Cove of Orleansbr2,4 Miles to Rock Harbor Beach in Easthambr0.6 Miles to Oceanair Himalayan Salt Cavesbr0.7 Miles to Hole in One for Breakfast and Lunchbr0.7 Miles to Hot Chocolate Sparrow for sandwiches, candy, chocolate and their famous Frozen Hot Chocolate br0.4 Miles to access the bike trail

Bed

Bath

Sleeps

$859.51

/ Nightly

Private Vacation Home

Stunning Home with In-Ground Pool!

Orleans, Massachusetts, United States

Summary:brbr15565 - Meeting House Meditation : Stunning Home with In-Ground Pool!brbrbrbrThe Space:brbrWelcome to the wonders of Orleans, Cape Cod, where the raw beauty of the Atlantic meets the quiet charm of Cape Cod Bay. Nestled between Eastham and Chatham, this coastal town blends small-town New England charm with unforgettable natural landscapes. Before you even have a chance to enter this gorgeous home, take in the stunning view of Meeting House Pond just over the horizon. brStepping into this incredible home, your jaw will drop when you see the towering ceilings overhead in the stylishly decorated living room. Play a quick tune on the piano before heading into the immaculate kitchen, with breakfast bar and center island, and access to the screened-in porch out back. This kitchen gives you ample counter space to prepare a feast for eight that you can then enjoy in the formal dining room.brThe home's primary suite is located on the first floor, with access to a private pergola covered porch, and full ensuite bathroom with large shower and detached soaking tub. Upstairs, the remaining sleeping quarters can be found.brbrThe ground floor of this home has a lovely additional entertainment space, a great escape to play board games or easily access the pool out back.brbrOutdoors, after splashing the day away in your private pool, you can lounge under the sun at numerous outdoor seating options. You can also head down to Meeting House Pond, where you can swim with the ducks and enjoy the pond water with herons flying above. brbrOther amenities include an outdoor shower, propane grill, and central A/C. Relaxation and meditation await your next vacation, at Meeting House Meditation!brbrbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-3 Floors (Ground Floor, 1st Floor + 2nd Floor)br-2,462 Sq. Ft.br-4 Bedroomsbr-Bedroom #1: 1 King Bed with En Suite Full Bathroom, 1st Floorbr-Bedroom #2: 1 Queen Bed, 2nd Floorbr-Bedroom #3: 1 Queen Bed, 2nd Floorbr-Bedroom #4: 1 Full Bed, 2nd Floorbr-3.5 Bathroomsbr-Bathroom #1: Full Bath with Shower, Ground Floorbr-Bathroom #2: Full Bath with Shower and Tub, 1st Floorbr-Bathroom #3: Full Bath with Shower and Tub, 2nd Floorbr-Bathroom #4: Half Bath, 1st Floorbr-Fully Equipped Kitchenbr-Central A/Cbr-TV with Cablebr-WiFibr-Washer & Dryer (Ground Floor)br-Private, Unheated, In-Ground Swimming Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)br-Screened-In Sunroombr-Deck with Pergola and Hammockbr-Outdoor Showerbr-Propane Grillbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0408682240brbrbrbrThe Neighborhood:brbrOceanside

Bed

Bath

Sleeps

$1036.55

/ Nightly

Private Vacation Home

Reconstructed History

Orleans, Massachusetts, United States

Vacation in splendor at this newly constructed home in East Orleans with bonus living space - the cottage! (New for 2021!) Built on the foundation of an 18th Century farmhouse, this custom built home features all of the beauty and amenities of a brand new home, yet has many charming characteristics that make it one of a kind. Peacefully located on a large lot in the Barley Neck area of East Orleans, this 3Bd/2.5Ba homes features high ceilings, open spaces and plenty of room with lots of natural light. The first floor boasts a large kitchen and dining room with reclaimed ceiling beams, bright living room with gas fireplace and French doors leading to the patio for outdoor grilling, dining and entertaining. The floor is completed with a queen bedroom and beautifully finished, custom tiled bathroom. The second floor features the king master bedroom, another bedroom with two full beds and a large bathroom with dual vanity. The lower level of the home is ideal for relaxing after a day at the beach; complete with a British pub theme, sofa sleeper and flat screen TV. Available to rent weekly from Sunday to Sunday. brbrNon-refundable $500 Administrative Fee, Cleaning Fee $525 (Linens included), plus applicable state and local taxes.

3

Bed

2

Bath

8

Sleeps

$871.07

/ Nightly

Private Vacation Home

Capeside: 540-O Vintage Luxury in Orleans

Orleans, Massachusetts, United States

This property is professionally managed by Pretty Picky PropertiesbrbrVintage Luxury in OrleansbrbrNEW Listing in 2026!brbrSleeps up to 10brLinens Included, Beds MadebrRents Friday to Friday in Peak SummerbrbrTucked away in the heart of Orleans, “Capeside” is a renovated antique home blending timeless Cape Cod charm with elevated, modern luxury—creating a retreat that feels both refined and effortlessly welcoming.brbrInside, the home has been thoughtfully reimagined with all-new furnishings, expertly curated to complement its original character. The stunning chef's kitchen anchors the main level, offering a beautiful and functional space for gathering, cooking, and entertaining. Just beyond, the primary living area invites relaxation with a spacious sectional—perfect for unwinding after a day at the beach.brbrA truly unique highlight is the converted gallery-turned-family room, where vaulted ceilings, original beams, and a wet bar create an airy, sophisticated space ideal for entertaining or quiet evenings in. A loft above adds an extra touch of charm and flexibility.brbrThe home features three beautifully appointed bedroom suites, each with a brand-new luxury bathroom. The first-floor suite offers convenience and comfort with a queen bed, while upstairs you'll find a serene king suite along with an additional guest suite -- each designed as a private retreat.brbrAn additional interior space provides exceptional flexibility, featuring daybeds with trundles and a large TV, along with a full bath—perfect for extra guests, kids, or a relaxed media room setup.brbrStep outside to enjoy the home's inviting exterior living areas, where a patio overlooks manicured grounds and a spacious lawn—ideal for outdoor dining, games, or simply soaking in the Cape Cod air.brbrPerfectly situated on the border of Orleans and Chatham, this home offers the ultimate Cape Cod lifestyle. Enjoy the rare convenience of being equidistant to the boutiques and dining of both downtown areas, while remaining just a short drive from the region's most iconic beaches. For water enthusiasts, you are only a half-mile from the Pleasant Bay town landing—perfect for launching kayaks and paddleboards. Whether you are looking to spend the day on an award-winning golf course or seeking a private, stylish retreat, this location provides an exceptional setting for your next escape.brbrPlease enter your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all rental terms less than 31 days that total 14.45%.brbrBe sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrIt's your vacation. Get Picky!®

3

Bed

5

Bath

10

Sleeps

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