Best Holiday rentals and Airbnb offers in Orleans, MA
Orleans, MA
25/06 – 30/06
SG$440/nighttotal: SG$2200 (5 )
New Brewster Condo Near Beach
1 2
apartment , Brewster
This renovated condominium is situated within the Ocean Edge Resort community, a short distance from Brewster's beaches, the Cape Cod Rail Trail, and local amenities. This apartment offers accommodation for four guests and features a modern kitchen with a dishwasher, air conditioning, a private patio with golf course views, and a garden, providing a comfortable base for exploring Cape Cod.
8.0 19 reviews
Orleans, MA
06/07 – 10/07
SG$574/nighttotal: SG$2296 (4 )
Charming Dog-friendly Home With Large Yard & Wifi
3 3
apartment , Eastham
This Eastham flat is located 800 metres from Kingsbury Beach and 3 kilometres east of Coast Guard Beach, offering convenient access to Cape Cod Bay and Atlantic Ocean shores. This property accommodates up to 8 guests with 3 bedrooms, 2 bathrooms, a well-equipped kitchen featuring a fridge, microwave, and dishwasher, air conditioning, parking, and a spacious garden ideal for outdoor activities.
9.7 85 reviews
Orleans, MA
06/07 – 10/07
SG$528/nighttotal: SG$2112 (4 )
Walk To Beach/kayaks/bocce/ocean Cottage
2 3
apartment , Eastham
This charming cottage is located just 0.16 kilometres from Thumpertown Beach in Eastham, a peaceful area close to Wiley Park and Great Pond. The property consistently receives excellent ratings for its location, cleanliness, and overall user experience. The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a private patio with a BBQ area, a bocce court, a badminton set, a hammock, and a lush vegetable garden, plus complimentary kayaks for exploring the bay.
10 49 reviews
Orleans, MA
06/07 – 10/07
SG$439/nighttotal: SG$1756 (4 )
Bright & Cozy With Patio, Grill Near Beach & Golf
1 3
house , Brewster
This Brewster guesthouse is situated in a quiet cul-de-sac near Nickerson State Park, a short distance (under 6.5 km) from Brewster town centre, Jackknife Beach, Wequassett Resort and Captains Golf Course. The self-catering property offers one bedroom, one bathroom, sleeping up to three guests, and features a fully equipped kitchenette, in-unit laundry, a shared patio with barbecue, and amenities including beach accessories and a smart TV.
10 7 reviews
Orleans, MA
25/06 – 30/06
SG$851/nighttotal: SG$4255 (5 )
Very Quiet Wooded Neighborhood In East Orleans
1 2
apartment , Orleans
This Orleans apartment, situated in a peaceful, wooded neighbourhood less than 3.2km from Nauset Beach, offers easy access to the town centre and other Cape Cod attractions. The self-catering flat comprises one bedroom, one bathroom, and in-unit laundry facilities, comfortably accommodating two guests and featuring a fully equipped kitchen and ample storage.
10 1 review
Orleans, MA
06/07 – 10/07
SG$663/nighttotal: SG$2652 (4 )
Peaceful Retreat On Chilton Lane
2 3
apartment , Brewster
This Brewster condo, situated on Chilton Lane near Widger Hole Pond, offers easy access to Brewster's beaches and trails. The two-bedroom, two-bathroom apartment sleeps five, boasting a modern kitchen with granite countertops, a pondside patio, and access to Ocean Edge Resort amenities (at an extra cost), including pools, a fitness centre, and kayak/paddleboard rentals at Blueberry Pond.
9.9 66 reviews
Orleans, MA
06/07 – 10/07
SG$917/nighttotal: SG$3668 (4 )
Cape Cod Sunscape. Orleans
2 3
apartment , Orleans
This Orleans holiday home, near the coast, is under 2km from Cape Cod Beaches and Rock Harbour Beach, and within 5km of Orleans Bowling Centre and the Edward Penniman House and Barn. The 102 square metre property sleeps six, boasting two bedrooms, a fully equipped kitchen with dishwasher, a private fenced garden with BBQ, plus a spa, fitness centre, and free WiFi.
9.9 56 reviews
Orleans, MA
06/07 – 10/07
SG$1082/nighttotal: SG$4328 (4 )
Lovely Two-acre Nature Oasis Near Nauset! Hot Tub!
4 3
apartment , Orleans
This secluded Orleans holiday home, situated between two conservation areas, is a short walk from Crystal Lake and Kent's Point, and 14.5km from Nauset Beach. The four-bedroom, three-bathroom property sleeps eight guests and boasts a hot tub, recreation barn with ping pong and foosball, a large deck with fire table and Weber gas grill, high-speed Wi-Fi (up to 1000 Mbps), and a well-equipped kitchen.
Orleans, MA
25/06 – 30/06
SG$564/nighttotal: SG$2820 (5 )
Sunny Orleans Cottage Near Skaket Beach! 1929
2 2
apartment , Orleans
This Orleans cottage is located in a quiet neighbourhood, just a short distance from the popular Skaket Beach. This property offers accommodation for up to five guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, a three-season sunroom, a finished basement with a ping pong table, a private deck with a gas grill, and an enclosed outdoor shower.
8.6 7 reviews
Orleans, MA
06/07 – 10/07
SG$477/nighttotal: SG$1908 (4 )
Hurry Back Cottage
1 3
apartment , Brewster
This two-bedroom, two-bathroom apartment in Brewster, Cape Cod, enjoys a central location offering easy access to beaches in Brewster, Chatham, Harwich and Orleans. The self-catering property sleeps six, features a fully equipped kitchen including dishwasher, and provides parking, air conditioning, and Wi-Fi; nearby attractions include the Captains Golf Course and Pleasant Bay Sailing Club.
Orleans, MA
25/06 – 30/06
SG$451/nighttotal: SG$2255 (5 )
60 M² Cottage ∙ 1 Bedroom ∙ 2 Guests
1 2
cottage , Eastham
This Eastham holiday let is situated on Town Cove, providing direct water access and a private dock, with Rock Harbor Beach and the Cape Cod Rail Trail within 3.2 kilometres. This 60 square metre bungalow accommodates two guests with one bedroom and one bathroom, featuring air conditioning, Wi-Fi, a kitchen with a fridge and microwave, and complimentary daily tickets to local attractions through the Xplorie partnership, alongside provided kayaks and canoes.
Orleans, MA
11/07 – 15/07
SG$680/nighttotal: SG$2720 (4 )
Wellfeet Retreat
3 3
apartment , Eastham
This Wellfleet flat offers proximity to Cahoon Hollow Beach, bayside waters for swimming, and downtown Wellfleet's restaurants, galleries, and shops, with the Wellfleet Drive-In Theater also nearby. This property accommodates up to six guests, featuring three bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a garden with a grill and fire pit, and an in-home washer and dryer.
Best family friendly Orleans, MA holiday rentals
Among the 741 accommodations in Orleans, MA, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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).
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
Orleans is a charming town, but for a real treat, head to the nearby Cape Cod National Seashore. Walk along the beautiful beaches, visit the Nauset Light, or explore the Salt Pond Visitor Center. The town of Chatham is also a short drive away, with its quaint shops and historic lighthouse.
What are the best Airbnb and vacation rentals in Orleans, MA?
The Cape Cod Rail Trail is a fantastic option for both walking and cycling. It stretches for 26 miles, offering picturesque views of the Cape Cod landscape. For a shorter walk, try the Orleans Town Beach path, offering stunning views of the Atlantic Ocean.
Orleans is a haven for outdoor enthusiasts. You can enjoy swimming, sunbathing, and surfing at the many beaches. The town also offers opportunities for kayaking, paddleboarding, and even whale watching tours. If you're looking for something more adventurous, try hiking or biking the trails at the Cape Cod National Seashore.
What are the best vacation rentals with a pool in Orleans, MA?
Orleans is ideally situated for exploring the Cape. You can easily reach the bustling town of Chatham, with its charming shops and restaurants. The historic town of Provincetown, known for its art scene and whale watching, is also within a reasonable drive.
What are the best rentals for families and kids in Orleans, MA?
Vacation rentals in Orleans often come equipped with comfortable amenities like kitchens, laundry facilities, and outdoor spaces like decks or patios. Many rentals also offer Wi-Fi, cable TV, and even private hot tubs.
What are the best rentals or Airbnbs with a jacuzzi in Orleans, MA?
The best time to visit Orleans depends on your preferences. Summer offers warm weather and plenty of sunshine, perfect for beach activities. Spring and autumn are milder, with fewer crowds and beautiful foliage. If you're looking for a winter escape, Orleans offers a peaceful and tranquil atmosphere.
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.
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.
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
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.
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.
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.
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.