Best Holiday rentals and Airbnb offers in 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.
9.8 9 reviews
Orleans, MA
25/06 – 30/06
SG$646/nightTotal: SG$3230 (5 )
Relax And Refresh In Eastham
1 2
apartment , Eastham
This Eastham flat offers a prime location, a mere 800 metres from First Encounter Beach and 1.6 kilometres from Coast Guard Beach. This newly available coastal retreat sleeps up to six guests across two bedrooms and a loft, featuring an open-plan living, dining, and kitchen area with air conditioning, Wi-Fi, and off-street parking.
9.2 11 reviews
Orleans, MA
11/07 – 15/07
SG$1385/nightTotal: SG$5540 (4 )
The Alpine/walk To Beach For 2 Or More!
3 3
apartment , Eastham
This Eastham holiday home, situated 0.16km from Thumpertown Beach and close to the Cape Cod Rail Trail, offers easy access to Nauset Light Beach and other local attractions. The 106 square metre property features four bedrooms, two bathrooms, sleeps up to twelve guests, and includes a fully equipped kitchen, screened porch, game room with pool and poker tables, and a Bocce court.
Orleans, MA
25/06 – 30/06
SG$645/nightTotal: SG$3225 (5 )
Light-filled Home Steps From Rail Trail - Near Pond, Bay & Ocean Beaches
3 2
apartment , Eastham
This Eastham holiday home is situated on a wooded plot, a short distance from the Cape Cod Rail Trail, 1.6 kilometres from Herring Pond, 3.2 kilometres from First Encounter Beach, and a brief drive from other Cape Cod National Seashore attractions. This 107 square metre holiday home accommodates up to six guests across three bedrooms and two bathrooms, featuring a well-equipped kitchen with a dishwasher and air fryer, a gas grill on the expansive back deck, a spacious garden, and indoor entertainment including a smart TV and Ping-Pong table.
9.5 4 reviews
Orleans, MA
25/06 – 30/06
SG$690/nightTotal: SG$3450 (5 )
Large Family Home & Yard: Your Cape Cod Getaway
1 2
apartment , Eastham
This Eastham holiday home enjoys a superb location, less than 1.6km from the Cape Cod Rail Trail, Fort Hill Trail, and Great Pond Beach, with First Encounter Beach (3.2km) and Nauset Light Beach (6.4km) also within easy reach. Sleeping eight, this three-bedroom, two-bathroom property boasts a full kitchen, air conditioning, Wi-Fi, a private garden with barbecue and fire pit, plus bikes and beach toys; a unique basement 'Connie's Pub' adds a quirky touch.
Orleans, MA
25/06 – 30/06
SG$563/nightTotal: SG$2815 (5 )
Serene Retreat With Cove Views
1 2
cottage , Eastham
This waterfront bungalow in Eastham offers direct access to Town Cove, featuring a private dock ideal for launching kayaks and canoes, and is conveniently located within 5 kilometres of the Cape Cod National Seashore, bay and ocean beaches, and local amenities. This dog-friendly property boasts a 60 square meter open-plan interior for two guests, with air conditioning, Wi-Fi, a kitchen equipped with a fridge and microwave, and includes daily $750 worth of tickets to local attractions via the Xplorie partnership.
9.9 86 reviews
Orleans, MA
25/06 – 30/06
SG$713/nightTotal: SG$3565 (5 )
Custom House W Central Ac At The Heart Of The Cape
1 2
apartment , Brewster
This three-bedroom Cape house is situated in a desirable location near the centre of Orleans, offering easy access to all the attractions of the Cape. The property features a spacious master suite with a private bathroom, two further bedrooms, a fully equipped kitchen, and a large private deck, ideal for enjoying al fresco dining.
Orleans, MA
11/07 – 15/07
SG$601/nightTotal: SG$2404 (4 )
121 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests
2 3
cottage , Eastham
This Eastham holiday home is located directly on Town Cove, offering private dock access for kayaking and canoeing, and is situated within 3.2 kilometres of Rock Harbor Beach and the Cape Cod Rail Trail. This 120 square metre bungalow sleeps four guests and features two bedrooms, two bathrooms, air conditioning, Wi-Fi, a kitchen with a fridge and microwave, a deck with outdoor dining and a grill, and includes the Xplorie program offering $750 worth of daily free tickets to local attractions.
Orleans, MA
11/07 – 15/07
SG$1077/nightTotal: SG$4308 (4 )
Ranch-style Retreat By Leavetown Vacations
3 3
house , Harwich
This ranch-style property is situated in Harwich, 19 kilometres from Cape Cod Gateway Airport, 23 kilometres from Nauset Lighthouse, and 26 kilometres from Wellfleet Bay Wildlife Sanctuary. This spacious 158 square metre dwelling accommodates up to 11 guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen with a dishwasher, air conditioning, a fireplace, and a terrace, with free WiFi provided.
Orleans, MA
25/06 – 30/06
SG$589/nightTotal: SG$2945 (5 )
Serene Retreat With Cove Views
1 2
house , Eastham
This Eastham holiday cottage is located approximately 8.4 kilometres from Nauset Lighthouse, with attractions such as Truro Historical Museum (30.6 kilometres), Commercial Street (41.8 kilometres), and Pilgrim Monument (41.8 kilometres) within a 30.6 to 43.5 kilometre radius. This property accommodates up to three guests with one bedroom and one bathroom, featuring air conditioning, a microwave oven, a fridge, and cable television, whilst being conveniently situated 10.3 kilometres from Wellfleet Bay Wildlife Sanctuary and 12.7 kilometres from Cape Cod National Seashore.
10 12 reviews
Orleans, MA
11/07 – 15/07
SG$903/nightTotal: SG$3612 (4 )
Lakefront Retreat W/ Deck, Dock, Sandy Beach, 4 Watercraft, <6 Mins To 2 Beaches
2 3
apartment , Orleans
This Orleans condo, centrally located near Crystal Lake, offers direct waterfront access with a private sandy beach and is within 1km of Nauset and Skaket Beaches. The 77 square metre property sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, and outdoor amenities including a patio, BBQ, and enclosed shower; kayaks and canoes are also available for use.
Orleans, MA
11/07 – 15/07
SG$650/nightTotal: SG$2600 (4 )
Peaceful Waterfront Cottage Escape
2 3
apartment , Eastham
This waterside cottage in Eastham offers direct access to Town Cove, with the Cape Cod National Seashore, bay and ocean beaches, local eateries, and cycle routes all within easy reach. This two-bedroom, two-bathroom holiday home accommodates four guests and includes a private dock with complimentary kayaks and canoes, a shared patio with a fire pit, an enclosed dog area, and the Xplorie programme providing $750 daily for attractions such as Island Cruises and Whale Watch.
Best family friendly Orleans, MA holiday rentals
Among the 741 accommodations in Orleans, MA, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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
What are some interesting places to visit in or near Orléans, 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?
Which walking or cycling routes are the best in Orléans, 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.
What sports or outdoor activites can visitors enjoy in and around Orléans, MA?
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?
What other towns or cities can be easily accessed from Orléans, 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?
What amenities are commonly available in vacation rentals in Orléans, 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?
What time of year is best to rent a vacation rental Orléans, 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.
Destinations nearby
Best Orleans, MA holiday rentals with a balcony
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.
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.
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).
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
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.
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.
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.
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.