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

Funky, Woodsy House Near Nickerson - Dog Friendly! - Orleans, MA
9.6 122 reviews
Orleans, MA
06/07 – 10/07
SG$604/nighttotal: SG$2416 (4 )

Funky, Woodsy House Near Nickerson - Dog Friendly!

3 3
apartment , Brewster
This Brewster holiday home is situated 15 metres from Nickerson State Park, a short walk from Cliff Pond and a cycle ride from Crosby Beach via the Cape Cod Rail Trail.
The three-bedroom property sleeps six, features a finished basement recreation room, fenced garden, and amenities including a washer/dryer, dishwasher, and outdoor shower, plus extended cable TV with streaming services.
The Mansion At Ocean Edge Resort & Golf Club - Orleans, MA
8.3 2767 reviews
Orleans, MA
11/07 – 15/07
SG$1412/nighttotal: SG$5648 (4 )

The Mansion At Ocean Edge Resort & Golf Club

2 3
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.
Charming Retreat Near The Ocean With W/d, Games, & Trails - Orleans, MA
10 4 reviews
Orleans, MA
25/06 – 30/06
SG$1334/nighttotal: SG$6670 (5 )

Charming Retreat Near The Ocean With W/d, Games, & Trails

5 2
apartment , Eastham
This five-bedroom Eastham holiday home offers direct access to the Cape Cod National Seashore and is a short walk to the beach and the Cape Cod Rail Trail, ideal for cycling and walking.
This 190 square metre property accommodates up to ten guests with four bathrooms, a well-equipped kitchen including a dishwasher, and a screened porch, alongside outdoor games and a deck with a grill for entertainment.
Ocean Edge Resort-pool Access-end Unit-2 Bdr/2 Bth - Orleans, MA
9.9 198 reviews
Orleans, MA
06/07 – 10/07
SG$647/nighttotal: SG$2588 (4 )

Ocean Edge Resort-pool Access-end Unit-2 Bdr/2 Bth

1 3
apartment , Brewster
This two-bedroom apartment is located in Ocean Edge, Brewster, a short drive from the Cape Cod Rail Trail, scenic Route 6A, a 36-hole golf course, and 10 Brewster bay beaches.
The apartment features a fully equipped kitchen, comfortable dining room, rear balcony, en suite master bedroom with TV/DVD player, second bedroom with bunk beds and a trundle bed, air conditioning, fresh linens, towels, bathroom toiletries, smart TVs, internet, DVDs, books, games, and a workspace.

Best Orleans, MA holiday rentals with a pool

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

Exceptional Mid-cape Oasis With Many Amenities! - Orleans, MA
9.6 23 reviews
Orleans, MA
25/06 – 30/06
SG$1849/nighttotal: SG$9245 (5 )

Exceptional Mid-cape Oasis With Many Amenities!

4 2
apartment , Harwich
This apartment is ideally located in Harwich, just 16km from the charming town of Chatham and 48km from Provincetown. The property has excellent user, location, and cleanliness ratings, indicating a high-quality stay.
This spacious home has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The apartment offers a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and parking, ensuring a relaxing and enjoyable stay.
Enjoy Harwich, Pool, Large Hot Tub & Ac! - Orleans, MA
Orleans, MA
06/07 – 10/07
SG$2635/nighttotal: SG$10540 (4 )

Enjoy Harwich, Pool, Large Hot Tub & Ac!

1 3
house , Harwich
This Harwich property is located 19 kilometres from Nauset Lighthouse and 21 kilometres from Wellfleet Bay Wildlife Sanctuary, offering convenient access to nearby Cape Cod attractions.
This detached house, covering 191 square meters, accommodates up to 31 guests with its 1 bedroom and 3 bathrooms, featuring a private balcony, hot tub, air conditioning, and complimentary Wi-Fi.
Cape Cod's Best!  Ocean Edge 2br Billington "A"! - Orleans, MA
9.9 44 reviews
Orleans, MA
25/06 – 30/06
SG$641/nighttotal: SG$3205 (5 )

Cape Cod's Best! Ocean Edge 2br Billington "A"!

1 2
house , Brewster
This Brewster townhouse, located in the Billington area, offers direct access to the 9th fairway of a Jack Nicklaus-designed golf course and is within easy reach of beaches, restaurants, and the Cape Cod Baseball League.
The two-bedroom, two-bathroom property sleeps six, boasts a family-friendly layout with a ground-floor master bedroom, updated kitchen with granite worktops and stainless steel appliances, private patio with gas grill, and access to multiple pools, hot tubs, saunas, tennis courts and fitness centres (passes required).
Wequassett Resort And Golf Club - Orleans, MA
9.3 348 reviews
Orleans, MA
11/07 – 15/07
SG$2662/nighttotal: SG$10648 (4 )

Wequassett Resort And Golf Club

1 3
resort , Harwich
The Wequassett Resort And Golf Club is situated in Harwich, a short drive from the centre of town and close to Cape Cod National Golf Center and the stunning Cape Cod National Seashore. It has received excellent ratings for both its location and overall experience, with guests praising its cleanliness and friendly service.
The resort offers a range of accommodation options, from spacious rooms to luxurious suites, all featuring comfortable sitting areas and private decks or patios. Guests can enjoy a variety of amenities, including a swimming pool, hot tub, fitness centre, tennis court, and a restaurant serving delicious seafood and American classics.

Frequently asked questions about holiday rentals in Orleans, MA

Destinations nearby

Best Orleans, MA holiday rentals with a balcony

Pleasant Bay Village Resort - Orleans, MA
9.6 458 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.
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.
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.
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.

Best Orleans, MA holiday rentals with parking

5 Bedrooms Ocean View Estate Overlooking Cape Cod Bay - Orleans, MA
9.4 57 reviews
Orleans, MA
06/07 – 10/07
SG$1605/nighttotal: SG$6420 (4 )

5 Bedrooms Ocean View Estate Overlooking Cape Cod Bay

5 3
apartment , Orleans
This Orleans holiday home, situated 1.2km from the town centre, Skaket Beach, and a cycle path, and a short walk from Rock Harbour, offers easy access to Orleans' attractions and the Cape Cod Trail.
The 325 square metre property boasts five bedrooms, four bathrooms, sleeps twelve, and includes a terrace, garden, spa, parking, and a fully equipped kitchen; nearby activities include kayaking, birdwatching, and fishing trips from Rock Harbour.
Eastham, Cape Cod - Town Cove Waterfront - Orleans, MA
9.0 99 reviews
Orleans, MA
11/07 – 15/07
SG$515/nighttotal: SG$2060 (4 )

Eastham, Cape Cod - Town Cove Waterfront

1 3
cottage , Eastham
This Eastham waterfront holiday home is less than 1.6km from the Edward Penniman House and Barn and Jonathan Young Windmill, and within 4.8km of Fort Hill and Eastham Windmill.
The 46 square metre property boasts one bedroom, one bathroom, sleeps five, and includes a fully equipped kitchen, patio, garden, free Wi-Fi, and parking.
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.
Sleeps 2-8/soaking Tub/firepit~burrows - Orleans, MA
9.9 103 reviews
Orleans, MA
06/07 – 10/07
SG$1024/nighttotal: SG$4096 (4 )

Sleeps 2-8/soaking Tub/firepit~burrows

3 3
apartment , Eastham
This Eastham holiday home is situated near the sea, less than 3.2km from the Three Sisters Lighthouses, Cape Cod beaches, and Arnold's Mini Golf.
The 121 square metre property offers three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, Wi-Fi, private patio, and fireplace.
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