Holiday Rentals in Orleans, MA

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Orleans, MA holiday rentals
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Best Holiday rentals and Airbnb offers in Orleans, MA

Best family friendly Orleans, MA holiday rentals

Among the 741 accommodations in Orleans, MA, here are the 4 best family friendly rentals

Cozy Cape Condo Minutes From Brewster Beaches - Orleans, MA
9.8 111 reviews
Orleans, MA
25/06 – 30/06
SG$590/nightTotal: SG$2950 (5 )

Cozy Cape Condo Minutes From Brewster Beaches

1 2
apartment , Brewster
This two-bedroom apartment is located on the Ocean Edge Resort Golf Course in Brewster, just a short distance from Breakwater Beach and Crosby Landing Beach.
The apartment features a fully equipped kitchen, a 55-inch 4K TV, a patio, and a flexible guest bedroom with a bunk bed and a single twin bed, making it ideal for families.
Light-filled Home Steps From Rail Trail - Near Pon - Orleans, MA
8.0 7 reviews
Orleans, MA
25/06 – 30/06
SG$560/nightTotal: SG$2800 (5 )

Light-filled Home Steps From Rail Trail - Near Pon

3 2
apartment , Eastham
This three-bedroom, two-bathroom holiday cottage in Eastham is ideally situated just metres from the Cape Cod Rail Trail, 1.6 kilometres from Herring Pond and a short bike ride to First Encounter Beach on Cape Cod Bay.
This property accommodates up to six guests and offers a large back deck with a gas grill, a garden, an indoor Ping-Pong table, and complimentary WiFi, with free parking for three vehicles.
Guest House Ocean Whisper - Orleans, MA
9.7 4 reviews
Orleans, MA
25/06 – 30/06
SG$1443/nightTotal: SG$7215 (5 )

Guest House Ocean Whisper

4 2
house , Harwich
Guest House Ocean Whisper is a beachfront property located in Harwich, just 19 kilometres from Wellfleet Bay Wildlife Sanctuary and 19 kilometres from Nauset Lighthouse. The house has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom holiday home spans 112 square metres and can comfortably accommodate up to 13 guests. The property offers a range of amenities, including a fully equipped kitchen, a private balcony, a garden, and parking.
209 M² House ∙ 4 Bedrooms ∙ 8 Guests - Orleans, MA
8.0 1 review
Orleans, MA
25/06 – 30/06
SG$847/nightTotal: SG$4235 (5 )

209 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 2
house , Eastham
This Eastham Cape Cod house, less than 1.6km from Thumpertown Beach and Campground and within 1.6km of restaurants including the Hole in One Bakery and Brickhouse Restaurant, offers a convenient base for exploring the Cape Cod National Seashore.
The 193 square metre property boasts four bedrooms, three bathrooms, sleeping up to eight guests, and features a family room with games, a deck with BBQ, and a large garden with a fire pit; smart TVs and Wi-Fi are also provided.

Best Orleans, MA holiday rentals with a pool

Among the 741 accommodations in Orleans, MA, here are the 4 best rentals with a pool

Pleasant Bay Village Resort - Orleans, MA
9.6 407 reviews
Orleans, MA
25/06 – 30/06
SG$760/nightTotal: SG$3800 (5 )

Pleasant Bay Village Resort

1 2
resort , Chatham
The Pleasant Bay Village Resort is located in Chatham, Massachusetts, just 4 kilometres from the Chatham Railroad Museum and 3.2 kilometres from the Chatham Municipal Airport. The resort is a 4-star property that has received excellent user ratings for its location, cleanliness and overall experience.
The resort offers spacious rooms with floral décor and private patios. Guests can enjoy a range of amenities including a seasonal outdoor pool, hot tub, game room, playground, free Wi-Fi, laundry facilities, a fitness centre, a restaurant and room service.
Ocean Edge, Bay Pines Villa Two Bedroom - Orleans, MA
9.1 21 reviews
Orleans, MA
11/07 – 15/07
SG$2905/nightTotal: SG$11620 (4 )

Ocean Edge, Bay Pines Villa Two Bedroom

2 3
house , Brewster
The Presidential Bay Villa is situated in the Ocean Edge Resort, a short walk from the private beach in Brewster, Cape Cod.
The villa offers 1200 square feet of living space with a king-size bed in the master bedroom, a queen-size bed in the second bedroom, and a pull-out sofa in the living room, comfortably accommodating a family or group of friends, and includes access to all Ocean Edge Resort amenities, including 5 pools, 3 restaurants, a golf course, tennis courts, a fitness centre, a beach bar, and more.
The Mansion At Ocean Edge Resort & Golf Club - Orleans, MA
8.3 2767 reviews
Orleans, MA
25/06 – 30/06
SG$1161/nightTotal: SG$5805 (5 )

The Mansion At Ocean Edge Resort & Golf Club

1 2
resort , Brewster
The Mansion at Ocean Edge Resort and Golf Club is located in Brewster, a short drive from the Cape Cod Museum of Natural History and the Wellfleet Drive-In Theater & Cinemas. It has consistently received very good ratings for location, cleanliness, and overall user experience.
The resort offers a range of accommodation options, including guest rooms with patios or balconies and villas with full kitchens and living rooms. Guests can enjoy a private beach, two swimming pools, a spa, a fitness centre, tennis courts, and a variety of dining options, including a pub, a tavern, and a seasonal terrace.
Townhouse At Ocean Edge 2b/2b + Loft - Orleans, MA
10 26 reviews
Orleans, MA
11/07 – 15/07
SG$1174/nightTotal: SG$4696 (4 )

Townhouse At Ocean Edge 2b/2b + Loft

2 3
apartment , Brewster
This two-bedroom apartment is located in Brewster, a short 10-minute drive from the beach and close to the Ocean Edge Resort, offering easy access to both relaxation and activities. The surrounding area is quiet and peaceful, perfect for a relaxing getaway.
The apartment is spacious and comfortable, with a cozy loft space and can comfortably accommodate up to six guests. It features a fully equipped kitchen, a washer and dryer, a patio with a grill, and access to Ocean Edge Resort amenities like multiple pools, tennis courts, and a pond for kayaking and stand-up paddleboarding.

Frequently asked questions about holiday rentals in Orleans, MA

Destinations nearby

Best Orleans, MA holiday rentals with a balcony

4 Bedroom Home By Leavetown Vacations - Orleans, MA
9.7 3 reviews
Orleans, MA
25/06 – 30/06
SG$1100/nightTotal: SG$5500 (5 )

4 Bedroom Home By Leavetown Vacations

4 2
house , Eastham
This Eastham holiday home is conveniently located a short walk from Campground Beach and within a few kilometres of Kingsbury Beach, Nauset Lighthouse, and Cape Cod National Seashore.
This spacious 209 square metre property boasts four bedrooms, three bathrooms, and can comfortably accommodate fifteen guests, featuring a fully equipped kitchen, air conditioning, private balcony, and free Wi-Fi.
Newly Built, Bayview House Steps From The Beach With Spacious Deck, W/d & Grill - Orleans, MA
9.8 6 reviews
Orleans, MA
25/06 – 30/06
SG$1524/nightTotal: SG$7620 (5 )

Newly Built, Bayview House Steps From The Beach With Spacious Deck, W/d & Grill

2 2
apartment , Eastham
This newly built Cape Cod-style holiday home in North Eastham offers direct access to a private bay beach, with ocean beaches, the Cape Cod Rail Trail, and the National Seashore all within a few kilometres.
This spacious 149 square metre holiday home accommodates up to four guests across two bedrooms and a den, featuring a fully equipped kitchen, open-plan living and dining areas, a finished basement with an Xbox One, and a deck with bay views.
3 Mi To Nauset Beach! Family Home W/ Private Yard - Orleans, MA
Orleans, MA
11/07 – 15/07
SG$906/nightTotal: SG$3624 (4 )

3 Mi To Nauset Beach! Family Home W/ Private Yard

4 3
house , Orleans
This family residence in Orleans is situated 4.8 kilometres from Nauset Beach and a 15-minute stroll from South Orleans Beach, with Nauset Lighthouse 11.6 kilometres distant.
This 157 square metre dwelling accommodates up to 15 guests with four bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a private garden, and free parking, offering convenient access to the Wellfleet Bay Wildlife Sanctuary (13.5 kilometres) and Cape Cod National Seashore (16.1 kilometres).
Beach & Town Walkable:family Friendly Cape Getaway - Orleans, MA
9.6 17 reviews
Orleans, MA
25/06 – 30/06
SG$1051/nightTotal: SG$5255 (5 )

Beach & Town Walkable:family Friendly Cape Getaway

4 2
apartment , Eastham
This Eastham holiday home is situated within 3.2km of Campground Beach and Thumpertown Beach, offering easy access to Cape Cod's coastline.
The four-bedroom, four-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private balcony, garden, free Wi-Fi, and parking; limited housekeeping is provided.

Best Orleans, MA holiday rentals with parking

Renovated 2nd-floor Corner Unit, New Interiors. Beach, Parking Passes On Us. - Orleans, MA
10 1 review
Orleans, MA
25/06 – 30/06
SG$441/nightTotal: SG$2205 (5 )

Renovated 2nd-floor Corner Unit, New Interiors. Beach, Parking Passes On Us.

1 2
apartment , Brewster
This recently renovated one-bedroom flat is located within the Ocean Edge resort in Brewster, offering convenient access to Cape Cod Beaches and Nickerson State Park, just 1.6 kilometres away.
This apartment accommodates up to four guests with a queen bed and a sleeper sofa, featuring a fully equipped kitchen, air conditioning, a balcony, garden access, and dedicated parking, with beach chairs and towels provided for your use.
Massasoit Hills House Close To Beach With Ac Yard & Deck - Orleans, MA
Orleans, MA
25/06 – 30/06
SG$679/nightTotal: SG$3395 (5 )

Massasoit Hills House Close To Beach With Ac Yard & Deck

3 2
house , Eastham
This Eastham holiday cottage is a 12-minute walk from Cooks Brook Beach and 1.4 kilometres from the Wellfleet Bay Wildlife Sanctuary.
This 98 square metre holiday home offers 3 bedrooms, 2 bathrooms, and accommodates up to 9 guests, featuring air conditioning, a fully equipped kitchen, a patio, a yard, and deck with outdoor seating, along with free private parking and Wi-Fi.
Relaxing Eastham Retreat With Waterfront Views - Orleans, MA
Orleans, MA
25/06 – 30/06
SG$671/nightTotal: SG$3355 (5 )

Relaxing Eastham Retreat With Waterfront Views

1 2
house , Eastham
Bell Buoy is a house situated in Eastham, a short drive from South Orleans Beach (3.1 kilometres) and Nauset Lighthouse (8.4 kilometres).
This property accommodates up to seven guests and offers air conditioning, a kitchen with a microwave, and a fireplace, with cable television for entertainment.
New Cape Cod Condo Near Beaches - Orleans, MA
Orleans, MA
25/06 – 30/06
SG$423/nightTotal: SG$2115 (5 )

New Cape Cod Condo Near Beaches

1 2
house , Brewster
This Cape Cod condominium in Brewster is located 19 kilometres from Nauset Lighthouse and 21 kilometres from Wellfleet Bay Wildlife Sanctuary.
This property offers 7 square metres of floor area, accommodates up to 7 guests with 1 bedroom and 1 bathroom, and includes WiFi, private parking, and a fireplace.
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