Houses found: 37 — for any number of people with any number of bedrooms in any town during any season

Orleans ~ Namequoit River (#550) This charming modern waterfront cottage is located in the exclusive section of Orleans called Mayflower Point where the Namequoit River meets Little Pleasant Bay. The secluded area boasts scenic water views, quiet nights and sounds of birds. 1 Bedrooms, 1 Beds, 1 Baths – 2 People, $1650/week; $1650/Early; $1300/Late; $1475/Spring Available Weeks: 6/28

Orleans (#1147) Adorable cottage located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. Enjoy the quiet setting of this lovely spot, with easy access to the salt water of the Harbor, a spacious deck with a lovely view. 1 Bedrooms, 3 Beds, 1 Baths – 2 People, $1250/week; $1250/Early; $1150/Late; $1200/Spring Available Weeks: 5/25, 6/1, 6/8, 6/15, 6/22, 8/17, 8/24, 9/14

Orleans ~ Skaket (#429) Location, Location! Popular duplex cottage, very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each with their own deck and central air-conditioning! 2 Bedrooms, 3 Beds, 1 Baths – 4 People, $1400/week; $1400/Early; $1400/Late; $1100/Spring Available Weeks: 6/22

Orleans (#1210) WATERFRONT COTTAGE! Nestled on two acres in Mayflower Point is this absolutely lovely, newly renovated cottage. Light and bright with cottage character throughout, painted exposed beams, skylights and glorious views out to Pleasant Bay. 2 Bedrooms, 2 Beds, 1 Baths – 4 People, $1850/week; $1650/Early; $1650/Late; $1450/Spring; $1450/Fall Available Weeks: 6/1, 6/8, 6/15, 7/13, 7/27, 8/24, 8/31, 9/7, 9/28

East Orleans ~ Mill Pond (#478) Spectacular Location! Simple, rustic cottage on a peninsula surrounded by salt water. Want to unplug? Escape from it all at this outstanding waterfront property offering exceptional privacy. PET-FRIENDLY, too-- $75 pet surcharge/per week 2 Bedrooms, 3 Beds, 1 Baths – 4 People, $1300/week; $1300/Early; $1300/Late; $1300/Spring Available Weeks: 9/14, 9/21

Harwich (#1283) Enjoy peace and privacy surrounded by nature only 50 yards from Cape Cod Rail Trial and 1 mile to Red River Beach on Nantucket Sound. This special 2-plus bedroom, 1.5 bath home offers charming vintage features with beautifully appointed with modern and stylish furnishings. With full amenities, including A/C and an outdoor shower. 2 Bedrooms, 4 Beds, 2 Baths – 5 People, $2600/week; $2400/Early; $2400/Late; $2000/Spring; $2000/Fall; $2000/Year-End Available Weeks: 5/25, 6/1, 6/8, 6/15, 6/22, 8/17, 8/24, 8/31, 9/7, 9/14, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26, 11/2, 11/9, 11/16, 11/23, 11/30, 12/7, 12/14, 12/21

Orleans ~ Bakers Pond (#1204) This location-- less than .1 mile from the beach at Bakers Pond-- feels removed from it all, yet is only a 5-minute drive to Skaket Beach, a 10-minute drive to Nauset Beach, and is near campsites, biking and hiking trails through Nickerson State Park. 2 Bedrooms, 4 Beds, 2 Baths – 6 People, $1800/week; $1750/Early; $1600/Late; $1550/Spring; $1550/Fall Available Weeks: 5/25, 6/1, 6/8, 6/15, 6/22, 8/24, 8/31, 9/7, 9/14, 9/21

North Eastham (#1207) Charming updated home located on a spacious lot not far from South Sunken Meadow Beach and Nauset Light Beach. Light and bright, freshly painted and meticulously kept, with a large master bedroom and newer kitchen and baths. Four AC units to keep you cool on hot summer nights. 3 Bedrooms, 4 Beds, 2 Baths – 6 People, $2300/week; $2000/Early Availablity to be determined

Orleans ~ Nauset Beach (#1251) On the way to Nauset Beach! Charming, classic pine paneled cottage with ductless A/C tucked away in 6-acre Nauset Farms Condominiums. Close to the East Orleans village and only 3/4 of a mile from Nauset Beach on The Atlantic. 3 Bedrooms, 5 Beds, 1 Baths – 6 People, $1450/week; $1350/Early; $1350/Late; $1350/Spring; $1350/Fall Available Weeks: 5/25, 6/1, 6/15, 9/14, 9/21, 9/28

Orleans (#1166) Wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point. Enjoy its own path down a slope to Lonnie's River that leads out to Pleasant Bay. Pets accepted with restrictions and $100 surcharge. Perfect for boating or kayaking. Now with central A/C! 3 Bedrooms, 5 Beds, 2 Baths – 6 People, $2800/week; $2800/Early; $1900/Late; $1900/Spring Available Weeks: 5/25, 6/1, 6/8, 6/22, 7/6, 8/31, 9/14

Orleans ~ Skaket Beach (#1161) AT SKAKET BEACH! This charming renovated 1927 Cape has ample room for 6, plus a lovely wraparound porch. The sunny interior features newly-painted floors, comfy furnishings throughout and excellent amenities. A tetherball set-up in the yard is fun for kids, and Skaket Beach is only steps away-- under .1 mile. DOG-FRIENDLY too! 3 Bedrooms, 4 Beds, 2 Baths – 6 People, $2500/week; $2500/Early Availablity to be determined

East Orleans (#1155) Great privacy in East Orleans abutting conservation land, this 3-bedroom, 2-bath contemporary home offers a bright and open floor plan and much privacy. Brand new ductless AC, kitchen & bathroom for 2019, too! 3 Bedrooms, 4 Beds, 2 Baths – 6 People, $2700/week; $2300/Early; $2200/Late; $2200/Spring Available Weeks: 6/29, 9/7, 9/14

Orleans ~ Town Cove (#1256) 'Westwinds' is a wonderful, classic expansive ranch located on beautiful Town Cove. Set far off the road, this very special property is surrounded by meadows, woodlands, and lovely waterfront views. 4 Bedrooms, 5 Beds, 2 Baths – 6 People, $4400/week; $4400/Early; $4400/Late Available Weeks: 8/17

Eastham ~ Heated Pool (#1059) HEATED POOL, HOT TUB and A/C! Swim in comfort and privacy, surrounded by lovely landscaping, and a koi pond then soak in the hot tub under the stars. 3 Bedrooms, 5 Beds, 2 Baths – 6 People, $3600/week; $3600/Early; $3400/Late; $3600/Spring Available Weeks: 6/1, 6/8, 6/15, 8/24, 9/7, 9/14

Brewster (#1277) Light-filled, renovated contemporary Cape on a quiet street not far from the sandy shore of Cape Cod Bay and beautiful Nickerson State Park. The circular driveway and welcoming front porch lead to an open floor plan. The charming dining area with skylights, cathedral ceiling and exposed beams opens out to a spacious deck overlooking a natural fenced-in yard that backs up to conservation. Spacious main floor primary bedroom has a Queen bed and large sitting area. The second level has two more bedrooms (1 w/Queen, 1 w/2 Twins) and second full bath. Newer furnishings and full amenities. FRIDAY changeover. 3 Bedrooms, 4 Beds, 2 Baths – 6 People, $2400/week; $2200/Early; $2200/Late Available Weeks: 8/23, 8/30

Orleans ~ Skaket Beach (#771) Location, location! Sweet and cozy house on a quiet lane just 2/10ths of a mile from gorgeous Skaket Beach on Cape Cod Bay. 3 Bedrooms, 4 Beds, 1 Baths – 6 People, $2350/week; $2350/Early; $2350/Late Available Weeks: 6/22, 7/6, 8/31, 9/7, 9/14

East Orleans ~ Nauset (#448) Charming period home located only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Attached apartment also available for rent. 3 Bedrooms, 5 Beds, 2 Baths – 6 People, $2350/week; $2350/Early; $2350/Late; $2350/Spring; $2350/Fall Available Weeks: 6/8, 8/17, 8/24, 8/31, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26

East Orleans ~ Nauset (#447) Spacious one-level apartment only 2/10ths of a mile from gorgeous Nauset Beach on The Atlantic. Attached Main House also available for rent. 3 Bedrooms, 5 Beds, 2 Baths – 6 People, $2150/week; $2150/Early; $2150/Late; $2150/Spring; $2150/Fall Available Weeks: 5/4, 5/25, 6/1, 6/8, 8/17, 8/24, 8/31, 9/7, 9/14, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26

Orleans ~ Skaket (#428) Popular duplex cottage very close to Skaket Beach on Cape Cod Bay. Simple and beachy, each side rents separately and has their own deck and central air conditioning! 3 Bedrooms, 5 Beds, 1 Baths – 6 People, $1900/week; $1900/Early; $1900/Late; $1500/Spring Available Weeks: 6/22, 6/29, 8/24

Orleans ~ Bakers Pond (#1250) Bright and airy newly renovated home in quiet neighborhood with easy access to beautiful Bakers Pond. Nickerson State Park is a half-mile away for more freshwater activities and hiking enjoyment. 3 Bedrooms, 4 Beds, 2 Baths – 7 People, $2000/week; $1800/Early; $1800/Late; $1800/Spring; $1700/Fall Available Weeks: 9/7, 9/14, 9/21, 9/28, 10/5, 10/12

Orleans ~ Skaket Beach (#1268) Light & bright and lovely 3-bedroom + den home with central A/C near Skaket Beach! Incredibly spacious with 2900 sq. ft, brand new furnishings and freshly painted throughout on a quiet lane 8/10 mile from the sandy shores of Skaket Beach on Cape Cod Bay. Main level features a very generous principal bedroom with full bath and laundry area, a large living room, separate den (with queen pullout), an oversized eat-in kitchen, and dining room. An expansive deck overlooks a large private backyard-- perfect for entertaining family and friends! The second floor has two more bedrooms, full bath, and a 'bonus' room. 3 Bedrooms, 7 Beds, 3 Baths – 8 People, $3400/week; $3100/Early; $3100/Late; $2900/Spring; $2900/Fall Available Weeks: 5/25, 6/1, 6/8, 6/15, 6/22, 8/31, 9/7, 9/14, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26

South Orleans ~ Pleasant Bay (#1284) This quaint, 4-bedroom home with three full bathrooms is quintessential Cape Cod. It's simple and private, beautiful, and has a private beach with a boathouse (partial use). DIRECTLY ON THE WATER. The view from the house is down a lovely meadow, approximately 60 feet to the beach. Beyond that, your view is of Hog and Sampson islands and Nauset Beach in the distance. 4 Bedrooms, 5 Beds, 3 Baths – 8 People, Available Weeks: 6/22, 6/29, 7/6

Orleans ~ Waterfront on Bakers Pond (#1205) Contemporary 3-level home with water views from every room and a private path to the pond only 75 feet away. Only .5 mile to Nickerson Park biking and hiking paths, 3 miles to Skaket Beach on the Bay. Relax in air-conditioned comfort in this 2800 sq. ft. open-concept home. With 3 exterior decks, a screened porch, patio and outdoor shower. Excellent amenities; kitchen has induction range and new cookware; living room offers a grand piano. Bakers Pond is ideal for swimming, kayaking, fishing, floating, or gazing at the water lilies... Sorry, no pets. FRIDAY CHECK-IN 3 Bedrooms, 6 Beds, 4 Baths – 8 People, $4800/week, $15000/month; $4400/Early; $4000/Late; $4000/Spring; $3600/Fall; $3600/Daylight; $1800/3-day Available Weeks: 5/17, 5/24, 6/14, 6/21, 7/5, 8/2, 8/9, 8/16, 8/30, 9/6

Orleans ~ Lakefront Retreat (#1181) At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with a brand new swim float for boating, fishing or swimming. Brand new ductless AC too! 3 Bedrooms, 5 Beds, 2 Baths – 8 People, $3400/week; $3400/Early; $3200/Late; $2500/Spring; $2500/Fall Available Weeks: 9/14, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26

South Orleans ~ Namequoit River (#1281) Waterfront with Private Dock on Namequoit River! Enjoy incredible views and access to the beautiful salt water of Pleasant Bay right from your own backyard! This spacious 3 bedroom + loft, 3 bath property sleeping 9 is a wonderful vacation spot to call your home away from home! The first level offers a gorgeous newly renovated kitchen with adjacent dining and living room, each with sliders leading to the spacious deck with spectacular views in every direction. Also on this floor is two bedrooms: the primary with a king sized bed and ensuite bath, and a second with a queen bed. A half floor up is the second level offering two additional sleeping areas: The first is an open 'loft' with 3 twin beds, a sitting area with a TV and a waterfront view. The second is the third bedroom with a queen bed. A bath is in-between the two. The home includes amenities such as wifi, gas grill, a/c and an amazing enclosed outdoor shower. Relax and enjoy boats passing and bird watching with privacy or kayak and SUP for boating adventures! 4 Bedrooms, 6 Beds, 3 Baths – 9 People, $4200/week; $4200/Early; $3000/Late; $3500/Spring Available Weeks: 7/6, 8/31

Orleans ~ Skaket (#1192) Walk to Skaket Beach! Spacious home with A/C, tucked away at the end of a quiet cul-de-sac. Only .6 miles to the sandy shore of Cape Cod Bay via a neighborhood path. Offering great privacy on 1.3 acres, the highlights of this home are its wonderful family room with cathedral ceiling and wood stove, brand-new kitchen, large screened porch that opens out to a expansive level yard. 4 Bedrooms, 7 Beds, 3 Baths – 10 People, $3500/week; $2975/Early; $2950/Late; $2450/Spring; $2450/Fall Available Weeks: 5/25, 6/1, 6/8, 9/7, 9/14, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26

East Orleans (#1195) Cape Cod elegance describes this beautiful home which sits peacefully at the end of the cul-de-sac adjacent to a cranberry bog. Ideal for the larger gathering with its great room with soaring cathedral ceiling, gorgeous eat-in kitchen, spacious tv loft, screened porch, deck and patio. 5 Bedrooms, 8 Beds, 4 Baths – 10 People, $5250/week; $5250/Early 2018 Dates & Rates to be confirmed

East Orleans ~ Ocean Harbor Association (#1142) Salt waterfront home located in the Ocean Harbor Association in East Orleans. This home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association tennis courts or deepwater boating access and swimming off the fabulous dock on the Mill Pond right around the corner. A wonderful vacation home-- DOG friendly too! 3 Bedrooms, 6 Beds, 3 Baths – 10 People, $4500/week; $4200/Early; $3600/Late; $3600/Spring Available Weeks: 5/25, 6/1, 6/8, 7/6, 9/14, 9/21, 9/28, 10/5, 10/12

Orleans ~ Crystal Lake (#1129) Crystal Lake — Designed to look like an illustration from a children’s fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, convenience, and fun in mind. A wonderful spot for a memorable vacation! 4 Bedrooms, 8 Beds, 3 Baths – 10 People, $3900/week; $3900/Early; $3900/Late; $2200/Fall; $1000/3-day Available Weeks: 6/22, 10/19, 10/26

Brewster ~ Breakwater (#982) Waterfront on Cape Cod Bay! Fantastic beachfront home with its own sandy shore of Breakwater Beach offering outstanding waterviews. Beautifully yet comfortably appointed throughout. 5 Bedrooms, 7 Beds, 5 Baths – 10 People, $12500/week; $12500/Early; $10500/Late Available Weeks: 6/21

East Orleans (#1275) Beautiful FIVE-bedroom home with A/C and full amenities is only minutes from Nauset Beach and East Orleans village! Ideal for larger gatherings and/or extended families offering two separate gathering spaces, two separate bedroom wings, air-conditioning, great comfort, privacy and a wonderful back yard oasis. And enjoy less traffic by renting Friday-Friday! 5 Bedrooms, 6 Beds, 3 Baths – 10 People, $5000/week; $5000/Early; $4500/Late; $4500/Spring; $4000/Fall Available Weeks: 5/24, 5/31, 6/7, 6/14, 6/21, 7/5, 8/23, 8/30, 9/6, 9/13, 9/20, 9/27, 10/4, 10/11, 10/18, 10/25

Orleans (#943) This charming and pristine contemporary ranch, nestled in a private wooded paradise-Mayflower Point, is minutes by foot to private salt and fresh water accesses for boating, swimming, or fishing. Launch a kayak at ''The River'', leading to Pleasant Bay, and the outer beaches, or, if you prefer, enjoy the freshwater of Pilgrim Lake. 4 Bedrooms, 8 Beds, 3 Baths – 10 People, $3900/week; $3600/Early; $3600/Late; $3300/Fall Available Weeks: 8/31, 9/7, 9/14, 9/21, 9/28, 10/5, 10/12

Orleans ~ Nauset Heights (#711) Expansive cottage on a bluff overlooking Nauset Inlet and the Atlantic Ocean. New upper level deck and private stairway down to the beach. 5 Bedrooms, 6 Beds, 2 Baths – 10 People, $5900/week; $5900/Early; $5900/Late; $4990/Spring; $3200/Fall; $3200/Daylight Available Weeks: 6/1, 9/28, 10/5, 10/12

South Eastham ~ Heated Pool (#409) Very spacious 5-bedroom home located in a lovely neighborhood offering its own heated in-ground pool and association tennis courts. A great location, close to the bike path and swimming. 5 Bedrooms, 8 Beds, 3 Baths – 10 People, $4900/week; $4900/Early; $4900/Late; $4900/Spring; $4900/Fall Available Weeks: 5/25, 6/1, 6/8, 6/15, 9/7, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26

Orleans (#1276) Wonderful East Orleans property with newer furnishings and central A/C, perfect for family and friends of all ages. Enjoy this terrific 4 bedroom home that affords space for everyone. Handicap-accessible, with 2-car garage with ramp into house. A great location with the neighborhood path to The River (.3 mile) for kayaking, Meetinghouse Pond, viewed from the front yard, only 1/2 mile away, and just 2.5 miles to gorgeous Nauset Beach. 4 Bedrooms, 8 Beds, 3 Baths – 11 People, $4500/week; $4500/Early; $3500/Late; $3500/Spring; $3500/Fall Available Weeks: 5/25, 6/1, 6/8, 6/15, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26

East Orleans ~ Pochet (#1279) Cape Cod elegance describes this expansive, fully air-conditioned home sitting peacefully on 2.4 acres in the desirable Pochet area of East Orleans. Beautifully renovated in 2022 with new furnishings throughout makes this 5 bedroom, 3.5 bath home ideal for the larger gathering-- Linens & Towels included and convenient to East Orleans Village and glorious Nauset Beach! 5 Bedrooms, 7 Beds, 4 Baths – 11 People, $6500/week; $6300/Early; $4900/Late; $5000/Spring; $4900/Fall; $4900/Year-End; $4900/Daylight; $4900/Winter Available Weeks: 12/30, 1/6, 1/13, 1/20, 1/27, 2/3, 2/10, 2/17, 2/24, 3/2, 3/9, 3/16, 3/23, 3/30, 4/6, 4/13, 4/20, 4/27, 5/4, 5/11, 5/18, 5/25, 6/1, 6/8, 6/22, 8/31, 9/7, 9/14, 9/21, 9/28, 10/5, 10/12, 10/19, 10/26, 11/2, 11/9, 11/16, 11/23, 11/30, 12/7, 12/14, 12/21

Brewster (#1260) Dramatic six-level contemporary home with association access to the freshwater of Blueberry Pond located just two-tenths of a mile from The Cape Cod Rail Trail and under two miles to the saltwater of Cape Cod Bay. A spacious great room with cathedral ceiling, skylights and hardwood flooring is located on the top level to take advantage of the panoramic view of Cape Cod Bay with a balcony facing the water and a covered porch that is perfect for dining al fresco. A few steps down is the kitchen and dining area with its own deck and water views. Six bedrooms (including 2 small bedrooms with two bunkbeds each) are on the various levels below. The ground level features a spacious family room that opens out onto a brick patio and lovely lawn. WHOLE-HOUSE A/C SYSTEM! , A great home for the extended family vacation accommodating up to 16 guests. Please note: The stairs between levels have open treads, 2 of the 3 bathrooms are accessed through bedrooms. Rents FRIDAY-FRIDAY. 6 Bedrooms, 12 Beds, 3 Baths – 16 People, $5880/week; $5880/Early; $4750/Late; $5670/Spring; $4550/Fall; $4550/Daylight; $1950/3-day No Available Weeks in 2024