Vacation Home Rentals By Owner In Orleans, MA

$2174.55

Beachfront house with amazing views of the Atlantic Ocean and Nauset Inlet.

Orleans, Massachusetts, United States

The best views of anywhere on the Cape! Welcome to Nauset Heights. This comfortable and classic cottage has it all: a sensational oceanfront location with 270-degree water views, classic Cape Cod charm, tons of sleeping space, and a modern kitchen for preparing big breakfasts and lobster feasts. From the expansive front porch, you’re only a few steps from the stairs to the beaches below — choose from placid Nauset inlet beach, which is ideal for families with small children; or walk across the sand to the outer beach, which makes for exceptional open-water swimming, boogie-boarding, and surfing. Plenty of room for everyone with five bedrooms (one queen, one full, and 6 twin beds) and two baths (plus an outdoor shower with, yes, ocean views). No pets. Available for weekly rental. Rate: $13,300/week in-season, $9,500/week off-season *State and local taxes apply*. $2500 Security Deposit (refundable).

5

Bed

2

Bath

10

Sleeps

$1133.01

/ Nightly

Private Vacation Home

3 Minute Walk to Nauset Beach

Orleans, Massachusetts, United States

Summary:brbrClassic Nauset Heights beach house, wraparound deckbrbrbrbrThe Space:brbr*Contact us for information on long-term booking opportunities!*brbrbrbrThis home is represented by Nauset Rental, a local vacation rental management company.brbrbrbrViews of Nauset Beach from almost every room of this 5 BR/3 BA classic, wood filled Cape Cod home in Nauset Heights. A 3 minute walk to world-renowned Nauset Beach and easy walk to inland waters and beach of Nauset Cove. Large wraparound deck with unobstructed views of Nauset's dunes and The Cape Cod National Seashore. This house has a very private view with just conservation area between it and the water, like your own private nature preserve. You will be renting the entire property. There is a garage and studio pictured but these are not used by anyone during the rental season - just owner storage. brbrbrbrCallanan's Pass provides a walking path directly to Nauset Beach just North of the public beach. This offers a respite away from the crowds of the public beach. The main floor has a whole side of the house facing the water with views through sliders and large picture windows from the kitchen and living room. A full deck just off the kitchen and living room with full views of conservation land below the Atlantic Ocean make you feel connected to the outdoors. Cool Ocean breezes come in right off the water in summer.brbrbrbrLarge classic home so close to Nauset Beach! Special unobstructed view of beach and national seashore lands. A short drive down a very private road off Nauset Heights leads you to this Cape Cod Classic. Wrap around decks offer a relaxing respite with views of Nauset Beach and dunes. There are no homes between you and the sand! This 5 bedroom home is light filled with water/ beach views from most rooms. Beautiful tub on the second floor, wooden floors throughout except for the large tiled lower living area. Exposed beams throughout the house, kitchen and living areas open to the view, Cozy bedrooms capture the spectacular Cape Cod light in the morning. brbrbrbrLayout of Bedrooms & Bathrooms: brbrLower Level brbrBedroom 1 - split king (can be separate into 2 twins) with A/C window unitbrbrBedroom 2 - two twins with A/C window unitbrbrFull bath with shower brbrMain Level brbrBedroom 3 - twin bed with A/C window unit brbrFull bath brbrUpper Level brbrBedroom 4 - primary bedroom with king bed with A/C window unitbrbrBedroom 5 - two twin beds with A/C window unit brbrFull bath with soaking tub brbrbrbr**Typically renters bring their own sheets, towels etc. Please inquire if you are interested in having linens delivered to the home for an additional fee.**brbrbrbrGuest Access: Whole home and grounds.brbrbrbrInteraction with Guests: As much or as little as they like.brbrbrbrOther Things to Note: Typically renters bring their own sheets, towels etc. That said, there are some great local companies we can refer you to that have rental linens available that can be delivered to the home for an additional fee.brbrbrbrOther Things to Note:brbr-

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Bath

Sleeps

$381.18

/ Nightly

Private Vacation Home

Cheerful Home Close to Bay and Town

Orleans, Massachusetts, United States

This bright and cheerful home approximately one half mile from either the bay or the center of Orleans. So close to Rock Harbor where you can charter a fishing boat or relax on the sandy beach while watching the boats come and go at high tide. Nicely located just under a half mile from Rock Harbor, just over a half mile to the bike trail or the center of town, 1.2 miles to Skaket Beach on the bay, and 3.8 miles to Nauset Beach on the ocean.brbrEnter this charming home to find a fully stocked kitchen, separate dining room, large, open living room, full bathroom with a combination tub and shower, master bedroom with a queen bed, and guest bedroom with an extra long twin bed with trundle.brbrThe second floor has a wonderful loft area with two twin beds on one side and a sitting area on the other side with a queen pull-out sofa.brbrThere is a nice covered patio area outside with outdoor furniture. There is also a level yard with small kettle pond in the back of the house. Enjoy an afternoon barbeque or rinse off after a long day at the beach in the exterior enclosed shower. brbrAmenities include: Central air conditioning (recently installed), wireless internet, 4 televisions with extended cable, dishwasher, electric range, drip coffee maker, washer and dryer in the basement, gas grill, outdoor furniture, umbrella, 3 beach chairs and misc. beach items. Sheets and Towels are not included but rental companies can be provided.brbr* Additional Fees:br- $220 Non-refundable Reservation Fee; $30 Damage Protection Fee; Guest Services Feebr- All Applicable Taxesbrbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* SHORTER STAYS AVAILABLE OFF-SEASON ONLY, THREE-NIGHT MINIMUM, LESS THAN 7 DAYS, $185 CLEANING FEE APPLIESbr* NO PETSbr* NO SMOKINGbr* OCCUPANCY: 6 (Adults and Children)br* PARKING FOR 3 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED, available to rent from local linen company, we are happy to provide informationbrbr* CONSIDER RENTING 32 OR MORE DAYS AND TAXES WILL BE ELIMINATEDbrbr****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.brbrClick the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover Compass rental!brbrAs a guest of Kinlin Grover Compass, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!

Bed

Bath

Sleeps

$622.37

/ Nightly

Private Vacation Home

Beach & Golf Hub w/ All-Season Sunroom in Cape Cod

Orleans, Massachusetts, United States

Families Welcome | Multiple Living Spaces | 2 Mi to Nauset BeachbrbrEmbark on your dream East Coast getaway and stay at this charming 5-bedroom, 3.5-bathroom Orleans vacation rental! Nestled near pristine beaches, lush golf courses, and other fun-filled activities, this abode offers an idyllic home base while you explore the Cape Cod area. Spend your days splashing in the saltwater, then head into town and indulge in an iconic lobster roll for dinner. Adventure awaits; book your trip today!brbr-- THE PROPERTY --brbrC0521792240brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 king bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 2 twin bedsbr- Bedroom 5: 1 twin bedbr- Additional Sleeping: 1 portable crib (bring your own sheets)brbrMAIN FEATURESbr- Smart TVs, books/board gamesbr- Dining tablesbr- Fireplace (decorative only)br- Furnished sunroom, multiple living areasbr- Spacious yardbr- GrillbrbrKITCHENbr- Refrigerator, microwave, stove/oven, dishwasherbr- Keurig & drip coffee makers, toasterbr- Cooking basics, dishware/flatwarebrbrGENERALbr- Free WiFibr- Central heating, window A/C unit, ceiling fansbr- Washer/dryerbr- Towels & linens, trash bags & paper towelsbrbrACCESSIBILITYbr- 2-story home, 2 steps required to enterbr- 1st-floor bedroom & full bathbrbrPARKINGbr- Garage (2 vehicles)br- Driveway (4 vehicles)brbr-- THE LOCATION --brbr- Close to Downtown Orleansbr- 2-11 miles to Nauset Beach, Skaket Beach, Coast Guard Beach & Lighthouse Beachbr- 2 miles to Cape Cod Rail Trail & 4 miles to Fort Hill Trailbr- 6 miles to Cape Cod National Seashore Salt Pond Visitor Centerbr- 6-12 miles to The Captains Golf Course, Chatham Seaside Links & Cranberry Valley Golf Coursebr- 9 miles to Cape Cod Museum Of Natural History & 14 miles to Cape Cod Museum of Artbr- 22 miles to Cape Cod Gateway Airport & 92 miles to Boston Logan International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 2 steps to enter; it features a bedroom and full bathroom on the 1st floorbr- The fireplace is decorative onlybr- Sheets are not provided for the Pack 'n Play; it is recommended that you supply your own

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Bath

Sleeps

$1478.32

/ Nightly

Private Vacation Home

Luxury home located 2 min walk from Skaket Beach. Sunny, spacious and private.

Orleans, Massachusetts, United States

This beautiful vacation home is located just a two minute walk from the popular Skaket Beach in Orleans, MA, a quaint seaside town that sits on the outer elbow of Cape Cod. With about 2,350 square feet to call your own, you’ll step into a clean, bright, modern and spacious space that offers excellent amenities and can comfortably sleep up to 8 people. With a perfect blend of quality and privacy that’s merely steps away from the sand, the area also boasts the popular Cape Cod Rail Trail bike path (about 1/2 mile away) and downtown Orleans (1 mile away), with a wide variety of shops and restaurants to enjoy along the way.brbrThe home has 2 master bedrooms, each with an en suite full bath. There are two more bedrooms with a pair of twins each. The twin bedrooms share another full bath. There is also a half bath next to the kitchen.brbrWith bright and modern stainless steel appliances, the kitchen also includes granite counter tops, a gas range, and a large center island.brbrThe space opens up to the dining area, which seats up to eight, while the open floor plan flows into the living room with plenty of comfortable seating and a large wall mounted Smart TV.brbrThere is a gas grill and dining table and chairs for 8 on the elevated private back deck. There’s also an enclosed outdoor shower on the side of the house.brbrThe house has central A/C, high speed Wi-Fi, cable and smart TV, as well as a Sonos Sound System.brbrThis home has the best location at Skaket Beach to enjoy long beach days and relaxing evenings barbecuing on the private back deck. brbrhttps://www.wildflowerlane.com

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Sleeps

$939.58

/ Nightly

Private Vacation Home

Sprawling Home With Private Association Lake Access (2289)

Orleans, Massachusetts, United States

Perched upon the top of a scenic hill with views overlooking Crystal Lake, this sprawling rental embodies the perfect relaxing getaway for your entire group. Updated for 2025 with brand-new kitchen appliances and a high-efficiency family room air conditioning unit, the home is designed for maximum comfort. You can leave your beach bags and sandy shoes in the spacious two-car garage for quick trips to the area’s pristine ocean beaches, then return to utilize the refreshing outdoor shower after a day in the salt air. The private backyard is a memory-making haven, complete with a deck and level lawn ideal for summer BBQs and classic yard games.brbrThe main level features a bright and inviting open floor plan that connects a renovated kitchen, a formal dining area, and a large family room centered around a 50 TV. Sliding doors make the transition to the back deck effortless, allowing you to move from cooking in the gourmet kitchen to dining under the stars in seconds. This floor also includes a dedicated bedroom with a queen bed, making it accessible for those who prefer to skip the stairs. Descending to the walk-out lower level reveals additional space to spread out, offering privacy and flexibility for diverse groups.brbrOn the second floor, you will find four more thoughtfully appointed bedrooms, including a generous primary suite with a king bed and another room with a comfortable queen bed. This floor is perfectly suited for families, offering a room with a twin daybed and a fun bunk room that houses three twin beds in total. To ensure a peaceful night's rest, every upstairs bedroom is equipped with a window air conditioning unit, and two full bathrooms service this level to keep morning routines smooth.brbrDirectly across the street, a short and private wooded path leads you to a secluded landing on Crystal Lake, putting the water’s edge just 150 yards from your front door. This state-stocked body of water is excellent for swimming and trout fishing, providing a tranquil freshwater alternative to the nearby salt bays. While the property feels like a private oasis, its convenient location allows you to access the vibrant shops and acclaimed dining of downtown Orleans in mere moments.brbrDogs permitted with owner permission and an added fee. BOOK NOW! An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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Bath

Sleeps

$730.17

/ Nightly

Private Vacation Home

4 Minute Walk to Nauset Beach

Orleans, Massachusetts, United States

Summary:brbrUnique Nauset Heights home with lookout deck, Full AC, & 250 yards to Nauset BeachbrbrbrbrThe Space:brbrThis home is represented by Nauset Rental, a local vacation rental management company.brbrbrbrAre you looking for a classic Cape Cod home in the Nauset Heights area of Orleans for your next Summer vacation Then look no further because we have the PERFECT home for you & it's just moments away from Nauset Beach! Nauset Lookout offers water views of the Atlantic Ocean, a spacious interior & nostalgic vintage vibes. As an added perk, delicious eats from Nauset Farms, The Barley Neck Inn, Whisk Cafe & The Rail are just a short car ride away.brbrbrbrThe main floor of the home is full of natural sunlight that showers in from an abundance of windows. Tall, vaulted ceilings in the living area surrounded by wood walls & beams, make the large open space the spot to be! The fully equipped kitchen has all the necessities you could need for preparing dinner and then grilling it up on the gas grill outside. Whether it's burgers & hotdogs, fresh caught local fish or ribeye steaks, somehow your dinner will just taste better when it is enjoyed outdoors on the expansive back deck. After dinner, curl up on one of the cozy couches in the living room and read one of the many books from the bookshelves or gather the family around the oversized dining table and play a board game. The possibilities are endless. brbrbrbrOne of the bedrooms on the main floor offers a king bed & wall of glass windows. If waking up early to warm Summer sunlight is too bright for you, pull the full length curtains shut and sleep in a bit longer. Boasting a queen bed & private access to the wrap-around deck, the second bedroom on the main floor is a cozy spot to ride out a rainy Cape Cod afternoon. Both the bedrooms on the upper level share a full bathroom with a tub/shower combo. The lower level of the home is the perfect spot for the kids in your group. One bedroom allows for the option of a split king when the two twin beds are pushed together. The additional bedroom on the lower level accommodates sleeping for four with a queen bed & twin bunk beds. A full sized bathroom with stand-up shower rounds out the lower level of the home.brbrbrbrAdditional perks to the home are an enclosed outdoor rain shower, washer/dryer, a reading library, mature garden landscape & mid-century artwork. This vintage Cape Cod home offers has many things that set it apart from others in the area (especially its proximity to Nauset Beach!). An abundance of memories with your family & friends could be made in this beautiful Nauset Heights home. Do not let the opportunity to have a magical Summer pass you by!brbrbrbrNauset Beach North is a short four minute walk from the house. There is a gorilla beach wagon in to transport all your beach toys!brbrbrbrbrbrBedroom & Bathroom LayoutbrbrLower Level:brbrBedroom 1 - 2 Twin Beds (can be pushed together for a split king)brbrBedroom 2 - Queen Bed & Twin Bunk BedbrbrBathroom 1 - Full Bathroom w/ Stand-Up ShowerbrbrbrbrMain Level:brbrBedroom 3 - King Bed & Wall of Glass Windows (Provided Full Length Curtains to Block Light)brbrBedroom 4 - Queen Bed & Private Deck AccessbrbrBathroom 2 - Full Bathroom w/ Tub/Shower CombobrbrbrbrLiving Room:brbrSleeper Bed (Full Size)brbr**Typically renters bring their own sheets, towels etc. Please inquire if you are interested in having linens delivered to the home for an additional fee.**brbrbrbrAmenitiesbrbrToasterbrbrStovebrbrOvenbrbrPots/PansbrbrBlenderbrbrDrip Coffee PotbrbrElectric KettlebrbrMicrowavebrbrRefrigeratorbrbrLobster PotbrbrServing Dishes & Serving UtensilsbrbrWireless InternetbrbrCable TelevisionbrbrHeatingbrbrAir Conditioning (mini splits on upper level, large head unit serving common areas and then two head units in upstairs bedrooms. Also in window and standing units just in case it needs extra cooling.)brbrWasher & DryerbrbrStereobrbrIndoor Woodburning Fireplace Insert brbrOutdoor Rain ShowerbrbrGas GrillbrbrTelescopebrbrBooksbrbrGamesbrbrBeach ChairsbrbrBeach CoolerbrbrBeach ToysbrbrDriveway ParkingbrbrbrbrBeach & Pond Distancebrbr5 minute walk to Nauset Beachbrbr3 minute walk to Mill Pondbrbr8 minute walk to Nauset Heights Association Beach Steps (inner Nauset Cove w/ warm/calm waters)brbr brbrbrbrbrbrWe welcome approved low-impact DOGS - Guest must reach out to Nauset Rental with dog details for approval either before making reservation or within 48 hours of submitting online reservation. There is an additional $100 fee if you choose to bring your dog along, and we will need to know the following information: brbrbrbrAny shedding brbrAny issues with accidents - urination or throwing up brbrAny issues with chewing furnishings brbrBarking while unattended or while attended brbrAre you confident you can leave property with no sign of your dog when you check out brbrDo you accept full responsibility for the behavior and impact of dogs in your group during your stay brbrbrbrOther Things to Note:brbr-

4

Bed

2

Bath

10

Sleeps

$1425.33

/ Nightly

Private Vacation Home

4 Acre Private Estate on the Water

Orleans, Massachusetts, United States

Summary:brbrSweeping water views, plenty of space for a large family getawaybrbrbrbrThe Space:brbr*Contact us for information on long-term booking opportunities!*brbrbrbrThis home is represented by Nauset Rental, a local vacation rental management company.brbrbrbrEscape to one of the largest parcels of waterfront properties left on Cape Cod. This spacious 4 acre private waterfront estate is located in the secluded Snow Point Association with private steps down to the water. Snow Point is a small peninsula of land in Orleans bordered by Rachel Cove, Town Cove and Woods Cove. You'll experience 180-degree views of the water from almost every room in this home, allowing to not miss the beautiful sunset view across the water. You can see Coast Guard Light, Fort Hill, Nauset Marsh and all of the above mentioned coves. You'll feel like you're on your own private island at the Cove Gardens property.brbr brbrPrivate access down to the water on your very own steps in the back yard allows you to bring along kayaks or stand up paddle boards and launch them right from the property. Explore the Cove and surrounding waters right from the back yard.brbr brbrThe 4- acre estate of waterfront lots is fully accessible with plenty of paths on the property to see the views from multiple perspectives! Enjoy the surrounding wetlands, trees and beautiful gardens. If you want to venture out, enjoy the Snow Point Association private beach just down the road which looks east across Nauset Marsh and Nauset Beach, or walk by beach around the whole point starting at the back yard, and wrapping around to Woods Cove, taking in miraculous waterfront views all along the way.brbr brbrLots of rooms and space make this a great home for a big family or a couple of families looking to vacation together. The property has six bedrooms located across 3 floors with plenty of room for extended families to enjoy their company or spread out into private spaces. There are AC's in all bedrooms in the main and upper floors. brbr brbrOn the main floor you'll find a very private primary bedroom with large full bathroom, a bedroom with two twin beds with French doors, and an additional half bath. There is a spacious living room with two seating areas, and a lovely dining room with plenty of seating with water views. brbr brbrUpstairs is a primary queen suite with a full primary bathroom. Additionally there is another queen bedroom and full bathroom, and a bunk room that is great for the kids! The bunk room has a large flat screen TV.brbr brbrThe lower level provides even more space with an additional sleeping area to spread out, equipped with a queen bed, full bath and sliding doors that lead out to the back yard and water views.brbr brbrThis sprawling waterfront property has endless outdoor spaces to explore and relax during your vacation, from the back deck and gardens to the stunning cove views across the lawn.brbrbrbrLayout of Bedrooms & Bathrooms: brbrMain Level brbrBedroom 1 - primary bedroom with queen bed and en suite full bath with 2 showers (one tub/shower combo, one walk-in shower)brbrBedroom 2 - sun room with two twin daybeds brbr1/2 bath brbrLaundry room brbrUpper Level brbrBedroom 3 - primary bedroom with queen bed and en suite full bath with tub/shower combo brbrBedroom 4 - queen bed brbrBedroom 5 - bunk room, with space to sleep 6 (1 twin bunk bed, two twin beds, and a queen bed)brbrFull bath with shower brbrLower Level brbrBedroom 6 - queen bed brbrFull bath brbrbrbrOther Things to Note: Typically, renters bring their own sheets, towels etc. That said, there are some great local companies we can refer you to that have rental linens available that can be delivered to the home for an additional fee.

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Bath

Sleeps

$305.58

/ Nightly

Private Vacation Home

Come enjoy Orleans and Chatham

Orleans, Massachusetts, United States

Spend a day at the beach or relaxing in the hammock in the beautiful back yard! Convenient to all that both Orleans and Chatham have to offer. A short 6 mile drive to the great restaurants and shops that downtown Chatham has to offer. Spend a day enjoying the rail trail and the charming village of Orleans just 3 miles from the house. The home next door is occupied by an onsite manager to help with any needs that may arise. Off street parking for 2 vehicles. Wifi available to enjoy your favorite TV shows or to work remotely. Large back yard with hammock, picnic table and grill to enjoy meals outdoors. After a day at the beach rinse off the sand in the outdoor shower.

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$747.5

/ Nightly

Private Vacation Home

Live the Good Life! Heated Pool, Walk to Ocean Beaches, Sleeps 12 in 6 rooms

Orleans, Massachusetts, United States

* Custom-built home in one of Orleans's most exclusive and peaceful neighborhoodsbr* Private heated pool with infinity edge and waterfall featurebr* Walk to Nauset Beach - one of the Cape's great open ocean beaches br* Ideal for 2-3 families; each floor has its own sitting/TV area, bed, and bath roomsbr* 100% Refund if you cancel and I'm able to rebook your staybr* Cook's kitchen with Viking 6 burner gas range and plenty of pots and pansbr* Second refrigerator in the garage for grocery and beverage overflowbr* Private sauna for dry or steam relaxation (main floor) br* Jetted soaking tub (main bathroom)br* Tons of windows, French doors, and decks help you enjoy the natural surroundingsbr* Office area with desk, chair, and landline if you need to sneak away for a work callbr* Furnished screened-in porch overlooking conservation area abutting the homebr* Pool area has new (2024) Extra Large Weber 4-burner grill, dining table, lounge chairs, and outdoor showerbr* Garage is stocked with bogey boards, beach cart, umbrellas, beach chairs and a coolerbr* Lower level is a walk-out with 8' ceilings, 5 piece leather sofa set, big screen TV, French doors leading to a small deck, and two bonus rooms set up to sleep 4 br* Central air conditioning plus two ductless heat/ac units in the lower levelbr* House has blankets, pillows, bath mats, kitchen towels, beach towelsbr* Guests provide linens & bath towelsbr* Please note - occupancy limits are strictly enforcedbrbrADDITIONAL DETAIL ON BEDROOMS and BATHSbr* Upper Level Beds: Owner's with King, 2nd bedroom with Queen +1 Twin. br* Upper Level Baths: Owner's en-suite bathroom + second full bathroombr* Main Level Beds: One bedroom with Queen, second bedroom with 2 Twinsbr* Main Level Baths: One full bath services the 2 bedrooms + 1/2 bath Powder roombr* Lower Level Beds: One room with Queen bed, One room with 2 Twinsbr* Lower Level Bath: One full bathroom services the 2 sleeping roomsbr* Lower level twin room does not have a closet

4

Bed

4

Bath

12

Sleeps

$795.03

/ Nightly

Private Vacation Home

5-bedroom Cape with a pool and yard games.

Orleans, Massachusetts, United States

Five-bedroom and three-bath Cape style home with large fenced backyard and an inground pool. Various yard games are available - outdoor ping pong table and corn toss. Short distance to Pleasant Bay, freshwater ponds, and the ocean. Approximately five miles from downtown Chatham and Orleans Center. A variety of local shops, and restaurants, and catch the Cape Cod Baseball under the lights just minutes away. (Our pool is not heated - the opening and closing is weather dependent). Three rooms on the first floor adjacent to the living room, kitchen, and dining room. The master bedroom has an attached private bathroom. The two smaller rooms share a bathroom in the main hall. The second floor has two larger bedrooms with recently renovated bathroom. Spacious living room with 70” TV, a couch and loveseat. Kitchen has all stainless steal appliances - 36” French door fridge, large OTR microwave, and electric glass top stove and oven. A toaster, coffee maker, and air fryer are available. Ductless mini-splits heat and cool each bedroom, which are individually regulated. The backyard is spacious, approximately 10,000 square feet, and has an inground pool and various yard games. The front door has a keyless entry. The code will be sent to you the day of your check-in. I will be available to help guests at any time. Write or call for support if you have any questions. Private dead-end road with access to Pleasant Bay. Town landing on route 28 is less than a mile away. Freshwater ponds in nearby conservation land with trails. The Captain’s Golf Course is two minutes away - the course has two par 72, 18 hole courses. Pleasant Bay Community boating offers a variety of programs for children and adults. You may not want to leave the pool side, but you may want to walk down to Pleasant Bay or a fresh water pond for a dip. Drive ten minutes to either downtown Chatham or Orleans Center. If your a cyclist or mountain biker, take a spin to the CC Rail Trail and Nickerson State Park. There is one bath towel per guest available. We do not provide pool or beach towels. Our home is NOT part of the Quanset Harbor Club (home association). You have access to the street and conservation land trails for walking but our guests do not have rights to the beach and landing at the end of Lake Drive. There is, however, a town landing at the end of Quanset Road, Portanimicut Road, and on route 28 (~1/4 mile from the house).

Bed

Bath

Sleeps

$599.37

/ Nightly

Private Vacation Home

Pondfront, 1 Mile to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15582 - Calm Waters: Pondfront, 1.4 Miles to Nauset Beach!brbrbrbrThe Space:brbrAlong the serene shores of Uncle Harvey’s Pond, this Orleans retreat offers a perfect blend of relaxation and adventure. Just 1.4 miles from the iconic Nauset Beach and a short mile from the charming East Orleans Main Street, this three-bedroom, two-bathroom home invites you to experience Cape Cod at its finest.brbrbrbrInside, the newly renovated upstairs suite accommodates four and boasts a private full bath, while two cozy bedrooms and an additional bathroom on the first floor provide comfortable arrangements for up to eight guests. Sunlight dances through the windows, framing water views that soothe the soul.brbrbrbrBegin your day with coffee from Whisk or a hearty breakfast at The Rail, then grab sandwiches from Nauset Farms and head to the beach to enjoy the waves—or try your hand at surfing! For a more leisurely pace, launch kayaks directly from the pond, or unwind on the expansive deck, soaking in the peaceful views.brbrbrbrEvenings beckon with simple pleasures: stargazing from the deck, enjoying ice cream from Smitty’s, or savoring a quiet night in this thoughtfully designed home. With water views, seamless indoor-outdoor living, and easy access to the best of Orleans, this retreat is more than a destination—it’s an invitation to reconnect with nature, family, and yourself.brbrbrbrExperience the magic of Cape Cod. Book your waterfront escape today and let the adventure begin.brbrbrbrHome Details:brbr-Dogs Welcomed (w/fee of $45/night per dog)brbr-Sleeps 8brbrBedroomsbrbr-Total 3brbr-1st Floor Bedroom: 1 Queen Bedbrbr1st Floor Bedroom: 2 Twin Bedsbrbr-2nd Floor Bedroom: 1 Queen Bed, 2 Twin BedsbrbrBathroomsbrbr-Total 2brbr-1st Floor: Full Bath w/ Showerbrbr-2nd Floor: Full Bath w/ Shower and Tubbrbr-Split System A/Cbrbr-WiFibrbr-Cable TVbrbr-Washer/Dryer brbr-Propane Grillbrbr-Outdoor Showerbrbr-Direct access to Uncle Harvey's Pondbrbr-3 Kayaks w/ life jackets brbr-Air Hockey Tablebrbr-Indoor Fireplaces are not for guest use(fines remitted)brbr-Please note outdoor amenities are available seasonallybrbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-Parking for 3 cars maximumbrbr-C0277742240brbrbrbrThe Neighborhood:brbrOceanside

3

Bed

2

Bath

8

Sleeps

$2747.99

/ Nightly

Private Vacation Home

Pochet Point Estate 056-O: Pochet Estate with Nauset Beach Access, Pool & Panoramic Views

Orleans, Massachusetts, United States

This property is professionally managed by Pretty Picky Properties.brbrPochet Point Estate with Nauset Beach Access, Pool & Panoramic ViewsbrbrNEW Listing for 2026!brbrSleeps 16brRents Friday to Friday during summer weeksbrLinens includedbrPool & Hot Tub open from Memorial Day to Columbus DaybrbrWelcome to your East Orleans retreat—an extraordinary water-view estate in the coveted Pochet neighborhood, offering refined coastal living just steps from Nauset Beach. This Patrick Ahearn designed seven-bedroom, seven full and-two half-bath home spans three levels plus a pool house of luxurious living, thoughtfully designed for gathering, relaxation, and coastal adventure.brbrThe main level features a gourmet kitchen with high-end appliances, a spacious island, and seamless flow to multiple interior and exterior dining areas. Gather in the elegant great room or one of several inviting lounge spaces, each offering comfortable style and tranquil views of Pochet Inlet and the surrounding salt marsh.brbrThere are 5 bedroom suites each with a King bed and private bath. There is one bedroom on the main level and an additional four bedroom suites on the second level. The third floor offers two family-friendly rooms—one with two twin beds and another with two sets of twin-over-twin bunks—ideal for kids or groups. There is also a full bathroom on the third level as well. brbrStep outside to your private resort setting: an oversized heated gunite saltwater pool, hot tub, and expansive pool deck designed for sun-soaked days and evening relaxation by the wood-burning fire pit. The magnificent Atlantic is your backdrop from the pool area. The ocean serenades you with the consistent calming wave action on the nearby shore. The pool house adds a layer of fun and function, complete with a game room, full bath, and laundry.brbrFrom the backyard, a private neighborhood boardwalk leads you through protected dunes to world-famous Nauset Beach—a breathtaking walk to one of Cape Cod's most iconic stretches of sand and surf. From the boardwalk you are accessing a secluded part of the beach to the south the public beach area. Plenty of space to set up camp and enjoy the rhythm of the Atlantic Ocean. brbrPerfect for large families or multi-generational groups, this estate combines modern luxury, coastal charm, and unbeatable location—the ultimate East Orleans escape.brbrPlease enter your travel dates in the 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. In addition, there are state and local taxes applied to all reservations less than 31 days in length 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! ®

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$927.91

/ Nightly

Private Vacation Home

Pleasant Bay Beachfront Property Plus!

Orleans, Massachusetts, United States

The owners refer to this one-of-a-kind property as Pleasant Plus. This unique beachfront home and certified wildlife habitat is located on Big Pleasant Bay with spectacular panoramic water and big sky views from the Atlantic Nauset barrier beach to the golf course at Chatham's Eastward Ho! Country Club.brbrSet on a bluff, the main house is an amazing, white-washed, full Post and Beam design. The first floor offers a family-friendly open floor plan with oversized fully equipped kitchen, dining area and living room with vaulted ceiling and open loft. There is one half bathroom in the foyer and one full bathroom with tub/shower at the end of a center hall, as well as two guest bedrooms; one with a queen bed and one with two twin beds.brbrStep out of the family room onto a full-length deck looking south onto the fall/winter kaleidoscope of down-Cape weather, certified natural wildlife habitat, and relentless local and migratory bird activity.brbrOn the second floor you will find a stunning master bedroom with king-sized bed where you will wake each day overlooking the breathtaking vista. This floor also features a separate full bathroom with shower, a third guest bedroom with one double bed and two small twin beds, and a fully tech-equipped work from vacation office setting and/or kid-friendly entertainment area for reading, creating, gaming or just relaxing.brbrThe lower walkout-to-beach level features a large glass-walled indoor bathroom to accommodate guest and beach-goers alike, as well as an all-weather (above freezing) outdoor shower with view of Strong Island.brbrStairs descend south from the Bay side of the house to the 1100 square foot boathouse/party house built directly on the private sandy beach where guests can isolate and commune with the Bay's nature and beauty up close and personal at any time, and in any weather.brbrPleasant+'s isolation from public activity (down a 1/3 mile private lane, into a gated cul-de-sac) make the property an ideal cathartic getaway from the realities of urban living. Unique features of this all-season home make it possible to experience the wonders of Lower Cape Cod's fall and winter natural and wildlife beauty, all the while remaining engaged and connected as remote work-from-home responsibilities may require.brbrAmenities include: Panoramic view of Pleasant Bay from all living areas, central heating and air conditioning, high-speed wired and WiFi internet service, full home office/WFH setting, first floor washer and dryer, 3 smart TVs with live streaming service, DVD/VHS player, telephone, light duty laser printer, gas grill, Keurig and drip coffee makers, enclosed outdoor shower, seasonal outdoor furniture, kayak, dinghy, beach chairs and recliners, sporting and aquatic gear, etc. Linens are provided for prime season rentals. For all other weeks, tenants can bring their own linens or rent them.brbrbr* Additional Fees:br- $300 Cleaning Fee. br- $220 Non-Refundable Reservation Fee; $30 Damage Protection Fee; Guest Services Feebr- All Applicable Taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO PETS (no exceptions)br* NO SMOKINGbr* OCCUPANCY: 10 (adults and children)br* PARKING FOR 4 VEHICLESbr* Sheets and towels provided on all weeks between May 30 - September 26, 2026. Linens are not included on any off-season stays. Tenants may bring their own or rent for $300.00.brbrbr****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.brbrClick the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover Compass rental!brbrAs a guest of Kinlin Grover Compass, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!

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$904.37

/ Nightly

Private Vacation Home

Spacious Game Room Close to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15529 - Beach Bend: Spacious Game Room Close to Nauset Beach!brbrbrbrThe Space:brbrThis exquisitely renovated home offers an idyllic retreat for up to 12 guests, boasting expansive outdoor spaces, luxurious accommodations, and an unbeatable location for an unforgettable vacation experience. Situated on a sprawling lot, both the front and back yards enchant with their picturesque beauty, providing three distinct outdoor seating areas for moments of relaxation and connection with nature.brbrEmbark on a leisurely stroll to Gilman Landing, a serene nature and kayak access point nestled on the shores of Pleasant Bay, where mornings are best spent savoring coffee amidst the tranquility of the coastal landscape. For endless sandy shores, Nauset Beach awaits less than 2 miles away, while Beach Road beckons with its array of charming shops and eateries, including Nauset Farms, The Barley Neck Inn, and Smitty's for irresistible ice cream delights.brbrThe allure of this vacation home extends beyond its enviable location, offering a spacious first floor that seamlessly merges a modern kitchen, plush seating area, and separate dining space, perfect for shared meals and cherished moments. Step onto the covered porch adorned with classic rocking chairs for shaded relaxation, or retreat to the second deck area featuring a large outdoor sofa and propane grill for alfresco dining under the stars.brbrThe first floor also hosts a serene Master bedroom with a king bed and en suite bathroom, while upstairs reveals three additional bedrooms, including a second Master with a sun-drenched walk-out balcony, a spacious bedroom with two queen beds and two twin beds, ideal for families, and a cozy retreat with a king bed. Entertainment abounds with a TV area and foosball table, ensuring fun for all ages.brbrCentral A/C throughout the home promises respite from the summer heat, ensuring comfort and relaxation throughout your stay. With its perfect blend of luxury and convenience in an unbeatable location, this home offers everything you need for a truly unforgettable Cape Cod getaway.brbrHome Details: br-No pets (fines remitted)br-Sleeps 12br-2 floorsbrBedroomsbr-Total: 4br-Master bedroom 1: 1 king bed, en suite full bathroom, 1st floorbr-Master bedroom 2 : 1 king bed, en suite full bathroom, 2nd floorbr-3rd bedroom: 1 king bed, 2nd floorbr-4th bedroom: 2nd Floor Kid's Suite with 2 queen beds and 2 twin beds, game roombrBathroomsbr-Total: 3.5br-1st floor: Full bath ensuite with shower and separate tubbr-2nd floor: full bath ensuite with showerbr-2nd floor: full bathroombr-1st floor: half bathbrOther Amenitiesbr-Central A/Cbr-Smart TV with Cablebr-WIFIbr-Washer and Dryer in 2nd floor laundry roombr-Outdoor Showerbr-Private Yardbr-Gas Grillbr-please note outdoor amenities are available seasonallybr-There is parking for a maximum of 4 carsbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-C0137542240brbrbrbrThe Neighborhood:brbrOceanside

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$590.07

/ Nightly

Private Vacation Home

Quaint Cottage Close to Skaket Beach (1912)

Orleans, Massachusetts, United States

If you are looking for the perfect location on Cape Cod, this charming Orleans cottage delivers on every level. Situated just moments from the calm waters of Skaket Beach, guests can enjoy the famous tidal flats that create a safe, unique environment for small children and a tranquil retreat for beach lovers. Outdoor enthusiasts will also appreciate being less than a mile from the Cape Cod Rail Trail, the renowned bike path that spans the length of the Cape. While the neighborhood offers a quiet, private community feel, you are only minutes away from the vibrant center of Orleans, where famous restaurants, cozy coffee shops, and eclectic boutiques await.brbrThe interior of the cottage is designed for comfort and ease, featuring an open layout that connects a cozy living area to an updated, eat-in kitchen. The family room is furnished with a comfortable new sofa, creating an inviting space to relax after a day in the sun. The main floor houses two bedrooms—one with a queen-sized bed and another with two twins—providing a convenient single-level living experience. For additional sleeping space, the lower level walk-out basement includes a double bed. brbrOutdoor living is a standout highlight of this property. The primary bedroom opens directly onto a large, sun-drenched deck overlooking a beautifully landscaped lawn. The backyard functions as a private oasis, fully outfitted with deck furniture for the whole family and a gas grill for classic summer barbecues. Tucked away in the yard is a lovely outdoor shower, a quintessential Cape Cod experience that makes rinsing off after the beach feel like a spa visit. The home’s central location in the elbow of the Cape provides effortless access to Nauset Beach, Rock Harbor, and the protected beauty of the National Seashore, making it an ideal base for exploring Chatham or Provincetown. brbrThe home offers all of the most requested amenities such as Central AC, wireless internet, and Roku for streaming all your favorite shows! *Sorry, no pets…no exceptions. 3 night minimum available with an added cleaning fee. 7 nights or more, the cleaning is included. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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Sleeps

$333.71

/ Nightly

Private Vacation Home

Cozy Home in Quiet & Convenient Area (1140)

Orleans, Massachusetts, United States

Tucked away on a peaceful wooded lot, this comfortable and pet-friendly 3-bedroom, 2-bath home offers the perfect balance of tranquility and convenience. Located just minutes from the Cape Cod Rail Trail, the center of Orleans, and beautiful Skaket Beach, you’ll be close to everything while still enjoying a private, quiet setting.brbrInside, the home features an updated kitchen with dining area, a welcoming living room, and a first-floor bedroom with two twin beds. Upstairs, you’ll find two additional bedrooms—one with a king bed and the other with a queen plus two twins—providing flexible sleeping arrangements for up to 8 guests. Two full bathrooms, Wi-Fi, and air conditioning window units add comfort and ease to your stay.brbrStep outside to enjoy the spacious yard, perfect for summer fun and evening cookouts. Fire up your choice of a gas or charcoal grill, relax on the deck, or rinse off in the enclosed outdoor shower after a day at the beach.brbrWith its convenient location and relaxed coastal charm, this home is ideal for families, friends, and even four-legged companions looking to make the most of their Cape Cod getaway.br br2 night minimums available off season with an added cleaning fee. Weekly rentals include cleaning fee. brPlease note: An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$354.61

/ Nightly

Private Vacation Home

Pet-Friendly Orleans Ranch (1560)

Orleans, Massachusetts, United States

This cozy 2 bedroom 2 bath ranch sits on a wooded lot in the heart of East Orleans. It is located a short drive to Nauset beach as well as the restaurants and shops of East Orleans and Orleans Center. The 2 bedrooms feature a Queen and a brand new King with en suite bath and the main bathroom was updated recently. The living room has an alternative sleeping area with a full sleeper sofa and 65 flat screen TV. Amenities like 2 A/C units, WiFi and Extended Cable TV make this a great little rental for any summer vacation. The deck features a gas grill for great summer barbeques. It is also pet friendly dog pen in back yard, so bring Fido or Fluffy! 3 night minimums available with and added cleaning fee. 7 nights or more include cleaning. An administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$565.47

/ Nightly

Private Vacation Home

Expansive Home by Orleans Town Landing (1086)

Orleans, Massachusetts, United States

This spacious and comfortable 2-story contemporary home sits on a wooded lot within a short distance to a public boat ramp to launch on Pleasant Bay and minutes away from Nauset, Skaket and Pleasant Bay beaches. brbrWith four bedrooms and three baths, it sleeps up to 8 effortlessly. The first level features a living room, family room, fully equipped kitchen, and two bedrooms, each with a queen-sized bed. The second floor offers another full bath along with the two additional bedrooms, one with a queen-sized bed and the second with two twins. Amenities include central A/C, wireless internet, washer/dryer, outdoor shower, an outdoor deck with dining table and a gas grill for summer barbecues. brbrAn administrative fee and applicable taxes may apply. Linens not provided. Guests may rent linens or bring their own.

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$1163.3

/ Nightly

Private Vacation Home

Waterfront retreat, private yet minutes to town and beach. Sleeps 7, 3 bedrooms

Orleans, Massachusetts, United States

Wake up to stunning, uninterrupted views of calm, crystal-clear waters in this beautifully updated 3-bedroom home, sleeping 7. Nestled in a private neighborhood just minutes from Nauset Beach and town, this serene retreat offers the ultimate waterfront experience.brbrStep out your door, and down the bank stairs and launch your kayak directly from the property. Wake up, grab your coffee and lounge on the deck while watching the seals glide by. Unwind with cocktails in hand while enjoying the Weber grill, lounge chairs, and outdoor dining area – all perfectly positioned to take in breathtaking sunsets.br Inside, this bright and airy home features an open-concept living, dining, and granite kitchen, ideal for entertaining. The first-floor primary bedroom with AC, ensures easy living, while upstairs, two bedrooms with AC provide a comfortable retreat for everyone. Additional highlights include 2 full baths, a refreshing outdoor shower with changing area, private front and backyard, bank stairs to the water and plenty of indoor and outdoor areas to lounge.brbrBook your slice of paradise today and make this private waterfront haven your home base for unforgettable summer memories!

3

Bed

2

Bath

7

Sleeps

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