Vacation Rentals By Owner In Orleans, MA

Summary:brbr15554 - On The Beachbrbr: Beachfront on Skaket Water Views!brbrbrbrThe Space:brbrLocated directly on famous Skaket Beach this cozy condo sleeps 7 and is the perfect choice for a true beachside getaway. Enjoy your morning coffee on the deck directly overlooking beautiful Cape Cod Bay. Step right out onto the beach to soak in some sunshine and go for a refreshing swim, stroll over to Ardath’s Snack Shack for lunch, and return to the home’s deck to sip a cocktail as you watch the ruby and peach colored sun set into the waves. Walking into “On The Beach” you will find a comfortable living room on the left and a dining area on the right. Both are framed with large picture windows featuring the amazing ocean view you would expect from a home directly on the beach. Down the hall is the bathroom and three bedrooms–one with a queen size bed, one with a twin bunk bed and one with a twin/full bunk bed. br brDowntown Orleans is a very short drive away and is full of many options for great boutique shopping, delicious restaurants, bars, bowling, and farmer’s market! Other amenities include WiFi, cable TV, gas grill, outdoor shower, window A/C units, washer/dryer. Fresh sheets and bath towels are provided free of charge. br brThe convenience of being located directly on the beach, and the memories of the ocean views from our home’s large picture windows will have you wanting to return year after year! br brHome Details: br-Sleeps 7 br-1 Floor br-Bedroom #1: 1 Queen Bed br-Bedroom #2: 2 Twin Beds (bunk beds) br-Bedroom #3: 1 Twin Bed + 1 Full Bed (bunk beds) br-Window A/C Units in Bedrooms br-Cable TV br-WiFi br-Outdoor Shower br-Washer/Dryer br-Spacious Deck br-Gas Grill br-No Pets (fines remitted) br-Water Views br-Walk to Water br-Waterfront! On the Beach! br-Sheets and Bath Towels Provided with Beds Made Upon Arrival br-Cleaned with Hospital Grade DisinfectantbrC0404622240brbrbrbrThe Neighborhood:brbrBayside

Beachfront on Skaket Water Views!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$567.18

Summary:brbr15545 - Sweet Retreat: Sleeps 8, Minutes to Nauset Beach!brbrbrbrThe Space:brbrEscape to the charming town of Orleans and create unforgettable memories at this delightful vacation rental. Nestled just minutes from Meeting House Pond and a short drive from both Nauset Beach and Skaket Beach, this home offers the perfect base for exploring the natural splendors of Cape Cod. In addition to an open backyard, you'll be greeted by a spacious deck adorned with a graceful pergola, providing a serene space for outdoor relaxation and dining. Two outdoor showers provide a refreshing way to rinse off the sand from your beach adventures. Bring your furry friends along, as this home warmly welcomes dogs, ensuring the entire family can enjoy a memorable getaway.brbrBoasting four bedrooms, this inviting retreat comfortably accommodates up to eight guests. On the second floor, you'll find a peaceful sanctuary with a queen bed in the master bedroom, along with an additional bedroom furnished with two twin beds. The first floor features a queen bed in one bedroom and a unique kids' suite complete with two twin beds, a cozy living area, and a convenient half bathroom.brbrSpend your evenings unwinding with the modern comforts of WiFi and cable TV, or enjoy whipping up fresh-off-the-grill delicacies that you bought from Nauset Farms, located conveniently just down the road.brbrNature lovers will delight in the proximity to the Cape Cod Rail Trail and Fort Hill Trail, offering endless opportunities for scenic walks and bike rides through picturesque landscapes. When it comes time to dine out, indulge in the flavors of the region at nearby culinary gems such as The Barley Neck, The Rail, Whisk.brbrWhat's more, this spacious 2,024 sq. ft. home provides a welcoming atmosphere, making you feel at ease from the moment you arrive. Convenient amenities, including a washer and dryer, ensure a hassle-free stay.brbrPrepare to immerse yourself in the beauty of Cape Cod and make this Sweet Retreat your home away from home.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-2 Floors (1st Floor + 2nd Floor)br-2,024 Sq. Ft.br-Bedroom #1: 1 Queen Bed, 2nd Floorbr-Bedroom #2: 2 Twin Beds, 2nd Floorbr-Bedroom #3: 1 Queen Bed, 1st Floorbr-Bedroom #4: Kids Suite with 2 Twin Beds, living room, and half bathroom, 1st Floorbr-2 Full Bathrooms, 1 Half Bathroombr-Bathroom #1: Full Bathroom with Tub/Shower Combo, 2nd Floorbr-Bathroom #2: Full Bathroom with Shower, 1st Floorbr-Bathroom #3: Half Bathroom, 1st Floorbr-Window Unit ACs in Bedroomsbr-WiFibr-TV with Cablebr-Washer and Dryer (1st Floor)br-Propane Grillbr-Private Yardbr-Deck with Outdoor Dining and Pergolabr-Lawn with Furniturebr-2 Outdoor Showersbr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrCO422332240brbrbrbrThe Neighborhood:brbrOceanside

Sleeps 8, Minutes to Nauset Beach!

Orleans, Massachusetts, United States

4

Bed

2

Bath

8

Sleeps

$429.19

Note: Previously occupied by a year-round renter; now available again for summer stays. (Friday-Friday)brEnjoy sunset views on Bakers Pond with access for kayaking around the shoreline. This three-story pine cabin offers an upstairs primary bedroom with a queen bed, sitting area, and full bath. An open main-level kitchen and living area with a 3/4 bath, and a walkout lower level with a second bedroom featuring two twin beds. A sliding door opens to a patio with access to the pond. I'm sorry, but NO pets are allowed.

Cabin

On Bakers Pond, an Upscale Cabin

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$1367.96

Beach Chairs & Towels | Lush Yard | 2 Living AreasbrbrClassic Cape Cod charm awaits at 'Captain’s Walk' cottage, just over half a mile from the calm, sandy shores of Cape Cod Bay. The 3-bedroom, 3-bath Orleans vacation rental sits on nearly an acre of landscaped grounds filled with native trees and blooms. Bike the Rail Trail, stroll to bay beaches, enjoy fresh lobster from nearby pounds, then wind down on the covered deck with a glass of wine as the sea air rolls in. You deserve this!brbr-- THE PROPERTY --brbrC0018542240 brbrSLEEPING ARRANGEMENTSbr- Bedroom Suite: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 2 twin bedsbrbrOUTDOOR LIVINGbr- Private patio w/ pergolabr- Gas grill, outdoor dining tablebr- 3 bikes, 6 beach chairs & 6 beach towelsbr- 0.86-acre lot w/ professional landscapingbr- Outdoor showerbrbrINDOOR LIVINGbr- Flat-screen TV w/ cable & DVD playerbr- Dedicated officebr- Gas fireplacebr- 6-person dining table & 3-person breakfast barbr- Open conceptbr- Board games & booksbrbrKITCHEN br- Stove/oven, refrigerator, dishwasherbr- Microwave, toasterbr- Keurig coffee maker, ice makerbr- Dishware/flatwarebr- Trash bags & paper towelsbrbrGENERAL br- Free WiFibr- Washer & dryer (detergent provided)br- Central A/C & heating, ceiling fansbr- Linens/towels, complimentary toiletriesbr- Iron/board, hair dryerbrbrFAQbr- Quiet hours (10:00 PM-8:00 AM)brbrACCESSIBILITYbr- 2-story cottage, 3 steps to enterbr- 1st-floor bedroom & full bathroombrbrPARKINGbr- Driveway (3 vehicles)brbr-- THE LOCATION --brbr- Quiet neighborhood within walking distance of Skaket Beachbr- 2 miles to the town of Orleans, Orleans Marketplace, Orleans Farmers' Market (Saturday mornings)br- 3 miles to Nauset Beach: excellent fishing & surfingbr- 6 miles to Captains Golf Course: double-championship par 72, 36-hole coursebr- 29 miles to Provincetownbr- 92 miles to Boston Logan Int'l 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- Please observe quiet hours from 10:00 PM to 8:00 AMbr- The maximum occupancy of 6 guests is strictly enforced at all times. Daytime or temporary visitors are not permittedbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story cottage requires 3 steps to enter; there is a bedroom and a full bathroom on the 1st floor

3 Bicycles Provided! Cape Cod Cottage w/ Deck

Orleans, Massachusetts, United States

Bed

Bath

6

Sleeps

$1039.33

Summary:brbrWalk to Pilgrim Lake and nearby saltwater bay landings for swimming, kayaking, and waterfront fun. Perfect for multi-family groups and pet friendly!brbrbrbrThe Space:brbrWelcome to Swaying Pines, a serene architectural retreat tucked away on an expansive wooded lot at the end of a magical private dirt road in East Orleans. Designed by a graduate of the Harvard Graduate School of Design in the mid-1960s, this original modern home is a striking example of thoughtful, era-defining architecture. The main house was built in the late 1960s, with a complementary guest house added in the 1980s, and together they create a harmonious compound connected by adjoining decks and a network of outdoor living spaces. The design intentionally optimizes natural light, cross-ventilation, and a seamless indoor/outdoor flow, allowing the home to feel fully immersed in its woodland surroundings.brbrbrbrThis ethereal oasis offers a rare sense of privacy and tranquility, alive with birdsong and local wildlife, yet ideally positioned for enjoying Cape Cod’s waterways. Residents and guests of Mayflower Point enjoy access to a small private beach on Pilgrim Lake, a peaceful freshwater retreat that is far less crowded than the public access points. Two additional private saltwater landings on Kent’s Bay and the Namequoit River provide exceptional opportunities for kayaking, paddleboarding, and exploring Pleasant Bay. After a day on the water or at the beach, rinse off in the outdoor shower — there’s nothing quite like warm water under the open sky.brbrbrbrArriving at the property, the home appears to rise organically into the tree canopy, blending effortlessly with the landscape. Inside, sliding glass doors flood the living spaces with natural light and open onto sun-drenched decks, while vaulted ceilings enhance the airy, open feel. The home’s modern design is complemented by multi-colored lighting and a charming collection of vintage board games from the 1970s and 1980s, adding personality and a nostalgic touch. The well-equipped kitchen flows into multiple dining areas, offering several options for indoor and outdoor meals — perfect for casual breakfasts, family dinners, or al fresco evenings under the trees. Sleeping accommodations are thoughtfully spread across the main house and guest house, featuring king, queen, and twin options, along with 3.5 baths. The guest house also includes a walk-in closet, providing added comfort and convenience for longer stays or extended families.brbrbrbrSwaying Pines is perfectly situated to enjoy the very best of Cape Cod. Skaket Beach on Cape Cod Bay and Nauset Beach on the Atlantic Ocean are each just three miles away, offering miles of sand, surf, and unforgettable sunsets. Nearby Kent’s Point features scenic, dog-friendly hiking trails, while Orleans town center — just over two miles away — offers charming shops, restaurants, and everyday conveniences. Chatham is eight miles away for additional exploration. Whether you’re drawn by the home’s iconic architecture, the private water access, or the peaceful woodland setting, Swaying Pines delivers a rare blend of design, comfort, adventure, and serenity.brbrbrbrLayout of Bedrooms & Bathrooms: brbrbrbrMain HousebrbrBedroom #1 - Queen bedbrbrBedroom #2 - Queen bedbrbrBedroom #3 - Two twin bedsbrbrbrbrBathroom #1 - Full bathroom with a tub and showerbrbrBathroom #2 - Full bathroom with a tub and showerbrbrbrbrGuest HousebrbrBedroom #1 - King bedbrbrBedroom #2 - Two twin bedsbrbrbrbrBathroom #1 - Half bathbrbrBathroom #2 - Full bathroom with a tub and shower brbrbrbr**This home provides linens and bath towels. Please remember to bring your own beach towels!**brbr**This is a dog friendly home. Please inform Nauset Rental if you plan to bring your pup along so we can send you screening questions.**brbrbrbrOther Things to Note:brbr-

New 2026 Expansive Modern Estate with Main & Guest House on 3 Wooded Acres

Orleans, Massachusetts, United States

5

Bed

Bath

10

Sleeps

$770.24

Discover the serene charm of the South Orleans Getaway, your perfect rental retreat nestled in a tranquil residential neighborhood. This elegant 4-bedroom, 2.5-bath colonial home boasts a spacious ambiance that is ideal for families or friends looking to unwind and reconnect.brbrUpon entering, you'll find yourself enveloped in comfort with multiple sitting rooms designed for relaxation and conversation. The expansive kitchen and dining area cater to culinary enthusiasts, providing a welcoming space for meals and gatherings. The second-floor primary suite features an ensuite bath for added privacy, while three additional bedrooms and a full bath are thoughtfully positioned upstairs, ensuring ample space for everyone.brbrStep outside to appreciate the picturesque garden views that add to the property's allure. Enjoy morning coffee or evening relaxation in the lovely outdoor spaces, perfect for soaking in the peaceful surroundings.brbrEquipped with modern amenities, the South Orleans Getaway also ensures your comfort and safety. Experience the convenience of a well-equipped kitchen, cozy living areas, and accommodations that cater to both social interaction and personal retreat.brbrLocated just a short drive from local attractions, restaurants, and beautiful beaches, there is no shortage of activities to explore during your stay. Whether you're seeking beach days or scenic strolls, this location offers the best of Cape Cod living. .3 miles to the John Kenrick Woods Trail and Little Pleasant Bay. Short drive to Nauset and Skaket Beaches.brbrBook your stay at the South Orleans Getaway today and make unforgettable memories in this delightful home away from home!brbrLocated just a short drive from local attractions, restaurants, and beautiful beaches, there is no shortage of activities to explore during your stay. Whether you're seeking beach days or scenic strolls, this location offers the best of Cape Cod living. .3 miles to the John Kenrick Woods Trail and Little Pleasant Bay. Short drive to Nauset and Skaket Beaches.brbrBook your stay at the South Orleans Getaway today and make unforgettable memories in this delightful home away from home!

South Orleans Getaway

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$515.36

Summary:brbr15569 - Nauset Haven: Spacious Home with Sprawling Yard!brbrbrbrThe Space:brbrThe sun shines down on the salty shores of Nauset Beach in Orleans, Cape Cod. Minutes from your front door, this world class beach awaits your vacation days, welcome to Nauset Haven!brbrWalk up the brick pathway, and step through the white front door, where a spacious home is ready for your vacation relaxation. To your right, the kitchen will be sure to be utilized, with loads of counter space to create your favorite picnic before bringing it to Nauset Beach. brbrThrough the kitchen, you can access the dining room, with peekaboo views of the water, as well as plenty of natural light through the windows on two sides. The living room has a large bay window, and ample seating to watch a movie before retiring for the evening. brbrTwo of the four bedrooms can be found on the first floor, each with a queen size bed. Upstairs, the remaining bedrooms can be found, one with 2 full sized beds and the other with 2 twin sized beds.brbrOutdoors, a large stone patio is the perfect spot to enjoy a meal outdoors while you watch your four-legged friends romp around the yard. A short walk down the road, Gilmans Landing is a great spot to launch a kayak, or watch the birds soaring over the salt marsh.brbrOther amenities include an outdoor shower, propane grill, and you’ll be sure to stay cool all summer long with central A/C. Escape to the Cape this summer and enjoy the natural beauty of Orleans, at Nauset Haven!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 8br-3 Floors (Ground Floor, 1st Floor + 2nd Floor)br-1,998 Sq FtbrBedroomsbr-Total 4br-1st Floor Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 2 Full Bedsbr-2nd Floor Bedroom 2 Twin BedsbrBathroomsbr-Total 2 br-1st Floor: Full Bathroom w/ Showerbr-2nd Floor: Full Bathroom with Shower/Tub combobr-Fully Equipped Kitchen with Dishwasherbr-Mini-Split A/Cbr-Smart Lock/Self Check-Inbr-WiFibr-Smart TV with Streaming and Cablebr-Washer & Dryer (1st Floor)br-Patio with Outdoor Diningbr-Propane Grillbr-Outdoor Showerbr-Private Yardbr-0.1 Mile to Gilman Landingbr-2.0 Miles to Nauset Beachbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0420442240brbrbrbrThe Neighborhood:brbrOceanside

Spacious Home with Sprawling Yard!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$479.96

This Cape Cod home is perfect for the beach lover, boater, kayaker or paddle boarder with proximity to Mill Pond and boating to the outer beach! Beautiful home offers 3 spacious bedrooms and two full baths on two levels. Main level features a sunny living room with gas fireplace and flat screen TV open to the dining space, a fully equipped kitchen with stainless appliances and farmhouse sink, one queen bedroom, one bedroom with twin bunk beds, a full bath with tub/shower combination and full sized stacked washer and dryer. Cozy three season porch with TV provides access to the new deck and yard. The upper level has the primary bedroom with king bed and peeks of the water, large closet and en-suite bathroom with a new walk-in shower. AC, Gas Grill & Outdoor Shower. New Deck for Summer 2022!

3 bed 3/10 mi to Mill Pond and Nauset Inlet

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$474.17

Nestled in the heart of Cape Cod, this stylish and comfortable vacation home at 13 Woodridge Road, Orleans, embodies coastal living and is just minutes from the Cape’s finest attractions, including Pleasant Bay, Nauset Beach, Skaket Beach, Captains Golf Course, and the scenic bike and hiking trails of Nickerson State Park, with top restaurants in Orleans, Chatham, Harwich, and Brewster a short drive away. Recently renovated, the home features a modern open kitchen with quartz countertops and stainless steel appliances, flowing seamlessly into indoor and outdoor dining spaces. Guests can refresh in the outdoor shower, complete with bluestone pavers and a wood-tiled changing area. Sleeping six across three bedrooms, the home offers a first-floor queen bedroom, two second-floor bedrooms with two twin beds each, a first-floor bathroom with a tub, and a stunning second-floor full bathroom with a walk-in shower. A 2025 dormer addition creates a cozy upstairs lounge with a Roku smart TV, complemented by a second lounge area with another smart TV. Central air conditioning keeps the home cool, with two new heat pumps added in 2025 to ensure the upstairs bedrooms stay comfortable on warm Cape evenings. Beach toys, an umbrella, and chairs are provided for seaside adventures. An administrative fee and applicable taxes may apply, and while linens are not provided, guests may rent them or bring their own.

Updated Vacation Home Close to Town and Beaches (2221)

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$532.76

2/10th's a Mile from Pleasant BaybrbrWarm and inviting, this remodeled antique home with marshland views is within 2/10th's of a mile from Pleasant Bay. This is a great area to rent or bring your own kayaks, paddleboards, or boats. brbrThe first floor of this charming home offers a beautiful renovated kitchen with granite counter tops and stainless steel appliances. There is also a dining area, living room with flat screen television, full bathroom with stall shower, and two bedrooms with window air conditioning-- both with two twin beds. brbrThe second floor has a full bathroom with a deep ball and claw foot style bath tub and a tiled stall shower. There are also three bedrooms with portable air conditioners, one with extra long twin beds, and two with one queen bed in each. brbrThe back yard has a wonderful area to relax by the fire pit and by the patio for barbecue. Please note: the washer and dryer is located in the basement with outside access only through the bulkhead.brbrLocation: This is a nice area approximately 5 miles or less to Orleans Center and Chatham Center. Nauset Beach on the ocean side is less than 6.5 miles away and Skaket Beach on the bay side is just under 6 miles. Take in a round of golf at the Captains Golf Club just 1.4 miles from this house or enjoy a dinner or a night of entertainment at the popular Wequasset Resort less than a mile away. brbrAmenities include: dishwasher, electric stove, microwave, Keurig and drip coffee makers, washer and dryer, three televisions with expanded cable and DVD player, wireless internet, gas grill and enclosed outdoor shower. Linens are not included. brbrFirst Floor: Bedroom #1 - Two Twin Beds, Bedroom #2 - Two Twin BedsbrSecond Floor: Bedroom #3 - Two Extra Long Twin Beds, Bedroom #4 - One Queen Bed, Bedroom #5 - One Queen Bedbrbr* Additional fees: $220 non-refundable reservation fee; $30 damage protection fee; guest services fee; all applicable taxesbrbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETSbr* FREE WIFI br* OCCUPANCY: 10 PEOPLE TOTAL (adults and children)br* PARKING FOR 4 VEHICLESbr* SHEETS AND TOWELS ARE NOT INCLUDED, available to rent from local linen company, we are happy to provide informationbrbrbr****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!

Refurbished South Orleans Antique Home Close to Pleasant Bay

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$525.26

This recently updated three-bedroom, 2 full baths and one half bathroom ranch style home is located on a quiet road. The residence offers a comfortable living room and dining area, three bedrooms with one King, one Full, and two Twin beds. For your comfort, this residence offers central air conditioning, a very nice deck, and a spacious backyard. The lower level offers a relaxing, large family room with a full bathroom. Located just a short drive to Rock Harbor, Skaket Beach and less than one mile to downtown Orleans. brbrNon-refundable $500 Administrative fee, Cleaning Fee $200, plus applicable state and local taxes.

Orleans Ranch Style Home Close to Town

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$867.58

Summary:brbr15517 - Endless Summer: Private pool 3 mins to Skaket Beach!brbrbrbrThe Space:brbrImagine days and nights at the pool with family and friends, cocktails at a combined bar and game room, and lawn games in a vast private backyard. This spacious 3,500 square foot home sleeps ten, and is the perfect place to get together with family and friends to make the most of your vacation. The outdoor area is truly the centerpiece of this home, offering a private pool, patio with seating for everyone, BBQ, and outdoor shower. For a change of scenery, beautiful Skaket Beach is just a three minute drive away. With plenty of dining and entertainment options in the area, such as The Captain Linnell House, Hog Island Brewery, Nauset Beach, The Jailhouse Tavern, Rock Harbor Grill, and Orleans Bowling Center, you will always find something fun to do nearby. Inside you will find a well stocked kitchen, washer/dryer, living room with mounted flat screen TV, master bedroom with king bed and nicely updated en suite full bathroom, a small bedroom with twin bed and crib, and another half bathroom on the first floor. Up the stairs from the living room are two more bedrooms, one with two queen beds and the other with a full bed and twin bunk beds. There is also a second floor lounge area/game room with a built in bar located above the garage, and central A/C throughout the house provides comfort on even the hottest of summer days. A ping pong table, corn hole set, and variety of board games will make Cape Cod days and nights with family and friends a time to remember. Don’t pass up this gem of a home for your next vacation!br brbrHome Details:br-No Pets (fines remitted)brbr-Sleeps 10brbr-2 Floorsbrbr-1st Floor Master Bedroom: King bed w/ en suite full bathbrbr-1st Floor Bedroom #2: Twin bed w/ cribbrbr-2nd Floor Bedroom #1: 2 queen bedsbrbr-2nd Floor Bedroom #2: Full bed and twin bunk bedsbrbr-Central A/C + Split A/C in game roombrbr-Cable TVbrbr-WiFibr-Washer/Dryerbr-Bar/Game Roombr-Tubbr-Outdoor showerbr-Private Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)br-Large private yardbr-Gas grillbr-Minutes from Skaket Beachbr-Sheets and bath towels provided with beds made upon arrivalbr-Cleaned with hospital grade disinfectantbrC0425922240brbrbrbrThe Neighborhood:brbrBayside

Private pool 3 mins to Skaket Beach!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$997.38

Summary:brbr15519 - Bayview Outpost: Private beach access Wrap around porch!brbrbrbrThe Space:brbrImagine watching the ocean waves break onto the shore while sipping your morning coffee from your private porch! This classic Cape Cod cottage, built in the 1890s, is just steps away from Cape Cod bay - with quiet serenity and a distant view of the bay. In addition to private beach access, the cottage features a wrap around porch with hammock, a screened in area for dining and relaxation, eat-in kitchen, enclosed outdoor shower, gas grill, and a spacious very private lawn for yard games. In addition, a great fire pit area is currently being built, and will provide an amazing spot to relax outside!brbrYou can walk over to Rock Harbor, or drive a few minutes to Orleans center for plenty of dining and entertainment options. There are three bedrooms and one full bathroom (with only a tub indoors - but with a huge outdoor shower), sleeping a total of six guests. The first bedroom includes a queen size bed, while the other two each have matching twin beds. Other amenities included are split A/C system for hot summer days, WiFi, cable, and a Smart TV for streaming. Linens and towels are always provided for your convenience. Join us by the sea this season and book now!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 6br-2 Floorsbr-2nd Floor Bedroom #1: Queen bedbr-2nd Floor Bedroom #2: 2 Twin bedsbr-2nd Floor Bedroom #3: 2 Twin bedsbr-Split A/C Systembr-Smart TV/cablebr-WiFibr-Tubbr-Outdoor Showerbr-Large LARGE Yardbr-Fire Pit br-Gas Grillbr-Private Beach Accessbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0448212240brbrbrbrThe Neighborhood:brbrBayside

Private beach access Wrap around porch!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$397.67

This charming cottage is located in the very popular Nauset Heights area within walking distance to Mill Pond, Priscilla Beach and Nauset Beach, including association rights to use the beach staircase. brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrThis warm and inviting, centrally air conditioned, one level home offers knotty pine walls throughout and has a full kitchen with dining area, ample living room, full bathroom with tub, and three separate bedrooms; one with a king bed, two with two twin beds each.brbrThere is a lovely patio and dining area in the rear of the house and an enclosed outdoor shower.brbrThe basement offers a washer and dryer and space to store bikes or kayaks.brbrLocation: This property is located approximately .2 mi. from Mill Pond, .3 mi. from Priscilla Beach, and .4 mi. from the Nauset Heights association access stairs or Callanan's Pass where there is no stair access. The Nauset Beach public parking area is about 1 mile away. Skaket Beach on the bay side of Orleans is 5.1 miles away. And the center of Orleans is approximately 3.4 miles away.brbrAmenities: Central air conditioning, heat, ceiling fans, wireless internet, gas stove, dishwasher, drip coffee maker, 1 television with streaming service, washer and dryer located in the basement, gas grill, and beach chairs. Sheets and towels are not provided. Linen rental companies can be provided upon request.brbr* Additional Fees: $220 non-refundable reservation fee; $30 damage protection fee (no security deposit required); guest services fee; all applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO PETSbr* NO SMOKINGbr* OCCUPANCY: 6 (Adults and Children)br* PARKING FOR 2 VEHICLESbr* SHEETS AND TOWELS ARE NOT PROVIDED, available to rent from local linen company, we are happy to provide informationbrbr**** 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 OKALI

This Cottage Delights in Nauset Heights. Near Mill Pond, Nauset Beach & Priscilla Beach

Orleans, Massachusetts, United States

Bed

1

Bath

6

Sleeps

$658.88

Summary:brbrExperience the best of indoor and outdoor living in this spacious, well-manicured property. Family and dog-friendly!brbrbrbrThe Space:brbrWelcome to Blue Heron Hideaway, a charming home at the end of a peaceful, single lane road, set in one of Orleans' most sought-after neighborhoods, just a short walk from a sandy Nauset Inlet beach. brbrbrbrThe home’s spacious layout flows naturally into landscaped grounds offering the best of indoor and outdoor living with plenty of room to spread out. Classic Cape Cod design and an exceptional location combine to create an ideal seaside retreat for families. A kayak and a paddle board are available on site, making it easy for outdoor enthusiasts to explore the sparkling local waterways.brbrbrbrThe house has two spacious decks, perfect for outdoor gatherings. Step inside to an eat-in kitchen, complete with a cozy breakfast nook framed by a bright bay window. The kitchen is well appointed with up to date appliances. Vaulted ceilings with wood beams give the room an airy, open feel. The kitchen connects to the backyard deck, perfect for grilling and outdoor dining. brbrbrbrPine floors continue throughout the first floor. The open layout of dining and living spaces with walls of windows offers a dining table for eight, ample comfortable seating, a smart TV, and additional dining space for six. Vaulted ceilings and a stunning inlaid stained glass window add architectural interest, while the bright white, airy Cape Cod design softened with warm wood tones makes every room feel sunny and cheerful. Off the main living area, a quiet den provides the perfect spot to curl up with a book to unwind, and offers the added convenience of a pullout couch for extra sleeping accommodations. All three bedrooms are cozy and well-appointed, including a convenient first-floor primary suite with a connected ensuite bathroom.brbrbrbrBlue Heron Hideaway is a perfect destination for families seeking a fun filled Cape escape. This vacation retreat offers a home base and easy access to a sandy beach - ideal for families looking to unwind away from the crowds. Guests who enjoy staying active on the water can swim or kayak in the nearby inlet or one of the many local ponds for those who prefer freshwater. Nearby sun-dappled hiking trails are perfect for family strolls or adventures with pups, while a short drive takes you to the world-famous shores of Nauset Beach or downtown Orleans, where vibrant galleries, local shops, grocery stores, and a variety of popular restaurants await. The expansive Cape Cod National Seashore is also easily accessible, offering endless opportunities for seaside exploration and adventure. Book your stay today for a truly memorable Cape Cod getaway!brbrbrbrLayout of Bedrooms & Bathrooms:brbrbrbrMain LevelbrbrBedroom #1 - Queen bedbrbrbrbrBathroom #1 - Half bathroombrbrBathroom #2 - Full ensuite bathroom with a walk in showerbrbrbrbrUpper Level brbrBedroom #2 - Queen bed and a twin trundle daybed brbrBedroom #3 - Two queen bedsbrbrbrbrBathroom #3 - Full bathroom with a walk in showerbrbrbrbrCommon Area brbrPullout couch in the denbrbrbrbr**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.**brbrbrbrOther Things to Note:brbr-

New 2026 Stunning East Orleans Home Steps from the Shores of a Beautiful Nauset Inlet Beach

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$646.51

Summary:brbr15515 - Lakeside Hideaway: Waterfront on Crystal Lake!brbrbrbrThe Space:brbrEmbark on a tranquil lakeside retreat at Lakeside Hideaway, where the gentle lapping of Crystal Lake's waters sets the rhythm for relaxation and rejuvenation. Nestled in the embrace of nature, this charming lakeside home invites travelers to unwind amidst the serene beauty of its surroundings.brbrbrbrStep inside to discover a cozy haven, where the well-equipped kitchen beckons for culinary adventures, and outdoor grilling offers a delightful option for al fresco dining. Gather with loved ones on the spacious screened-in porch, where evenings are spent playing games, sharing stories, and savoring the enchanting ambiance of lakeside living.brbrbrbrOutside, the freshwater lake awaits, mere steps from your front door, inviting you to indulge in leisurely activities such as kayaking/paddle boarding (provided in shed on property) fishing, swimming, or simply lounging shoreside in the embrace of nature's tranquility. And should the allure of the salt water beckon, the renowned Nauset Beach and Skaket Beach are just a short drive away, offering endless opportunities for seaside adventures.brbrbrbrComplete with modern amenities including an outdoor shower, propane grill, and central A/C, Lakeside Hideaway ensures a comfortable and enjoyable stay for guests seeking the ultimate lakeside getaway.brbrbrbrWhether basking in the glow of the sun-kissed waters, savoring the serenity of lakeside sunrises and sunsets, or simply embracing the joys of lakeside living, Lakeside Haven promises an unforgettable vacation experience for all who seek refuge in its tranquil embrace.brbrbrbrHome Details:brbr-No dogs (fines remitted)brbr-Sleeps 6brbrBedroomsbrbr-Total 3brbr-1st Floor Bedroom: 1 Queen Bedbrbr-1st Floor Bedroom: 2 Twin XL Bedsbrbr-1st Floor Bedroom #3: 2 Twin BedsbrbrBathroomsbrbr-Total 2brbr-1st Floor: Full Bathroom w/ Showerbrbr-Ground Floor: Full Bathroom w/ ShowerbrbrOther Amenitiesbrbr-Central A/Cbrbr-Fireplace NOT for guest use (fines remitted)brbr-TV with Cablebrbr-Smart Lock/Self Check-Inbrbr-WiFibrbr-Washer/Dryer (Ground Floor)brbr-Outdoor Showerbrbr-2 Kayaks, 2 Paddle Boards, Lifejacketsbrbr-Propane Grillbrbr-Screened-In Porchbrbr-Deck with Outdoor Loungingbrbr-10 Feet to Crystal Lakebrbr-Please note outdoor amenities are available seasonallybrbr-There is parking for a maximum of 3 carsbrbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbrbr-Cleaned with Hospital Grade Disinfectantbrbr-C1626731400brbrbrbrThe Neighborhood:brbrBayside

Waterfront on Crystal Lake!

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$958.5

Summary:brbr15506 - Shipmates Beach House: Private Beach and Roof Top Deck!brbrbrbrThe Space:brbrDiscover coastal living at Shipmates Beach House, nestled in the pristine beauty of Orleans, Cape Cod's hidden gem. With private access to the renowned Nauset Beach, this stunning two-story retreat beckons travelers to indulge in the ultimate seaside escape.brbrAs you approach this home, prepare to be captivated by its inviting charm. Step inside to unveil an open floor plan with exposed beam ceilings, creating an ambiance of rustic elegance. The living room offers a sanctuary of relaxation, while the kitchen provides ample space for culinary creations before gathering around the dining table bathed in natural light from the near floor-to-ceiling windows.brbrAfter days filled with Cape adventures, retire to one of the three bedrooms, each offering a haven of privacy and comfort to ensure restful slumber for every guest. Outside, a lush grass yard invites leisurely activities and yard games, while the rooftop deck offers a special vantage point to soak in the Cape Cod sun all vacation long.brbrJust minutes away, the world-famous Nauset Beach awaits, where the soft sands and gentle waves beckon for a day of seaside bliss. Complete with modern amenities including a washer and dryer, charcoal grill, and outdoor shower, Shipmates Beach House offers the perfect blend of comfort and convenience for an unforgettable Cape Cod getaway.brbrWhether swabbing the deck or hoisting the mast, come relax and rejuvenate at Shipmates Beach House, where every moment is infused with the magic of coastal living.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 6br-2 Floors (1st floor + 2nd floor)brBedroomsbr-Total: 3br-1st Floor Bedroom: 1 King Bed w/ en suite Bathroombr-2nd Floor Bedroom: 2 Twin Bedsbr-2nd Floor Bedroom: 2 Twin BedsbrBathroomsbr-Total: 2br-1st Floor: Full Bathroom w/ Shower/Tub combo (en suite King Bedroom)br-2nd Floor: Full Bathroom w/ ShowerbrOther Amenitiesbr-Wood Stove not for guest use (fines remitted)br-Living Room with Cathedral Ceiling and Loftbr-WiFibr-TVbr-Mini-Split A/Cbr-Washer and Dryerbr-Screened in Porchbr-Private Yardbr-Deck with Outdoor Diningbr-Rooftop Deck with Outdoor Loungingbr-Outdoor Showerbr-Charcoal Grill (bring your own charcoal)br-Please note outdoor amenities are available seasonallybr-Parking available for a maximum of 4 carsbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0407292240brbrbrbrThe Neighborhood:brbrOceanside

Private Beach and Roof Top Deck!

Orleans, Massachusetts, United States

Bed

2

Bath

6

Sleeps

$1883.8

Escape to the charming Briar Woods neighborhood in Orleans, where unforgettable family memories await. Just a quick four-minute drive to the stunning Nauset Beach, our vacation home is perfectly situated for beach lovers and explorers alike. A Brand New In-Ground Saltwater Heated Pool Hot Tub in 2025!*brStep inside and be greeted by a spacious family room featuring soaring ceilings that extend to the second floor, creating an inviting and airy atmosphere. The open-concept design seamlessly connects the living area, kitchen, and dining space, making it ideal for gatherings and family meals. Double glass doors lead you out to a lovely deck that overlooks the newly fenced yard, where your private oasis awaits complete with a luxurious saltwater heated pool and hot tub, all surrounded by elegant travertine tiling.brRetreat to the first master bedroom, a serene haven with a king-size bed, stunning new hardwood floors, and a private entrance to a beautifully designed master bathroom. Upstairs, you ll find another spacious master bedroom with high ceilings and a king-size bed, along with a cozy second bedroom featuring two twin beds perfect for kids or guests.brThe newly finished basement offers a fantastic hangout space for the kids, complete with a bedroom with 2 twins to ensure everyone has their own space.brAdditional amenities include central air conditioning, an outdoor shower for rinsing off after beach days, a convenient first-floor washer and dryer, and a one-car garage equipped with a ping pong table for some friendly competition. Additional space above the garage was a 2 twin trundle bed for flexible sleeping options.

Briar Springs Pool/Spa Getaway

Orleans, Massachusetts, United States

Bed

Bath

Sleeps

$374.33