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Best Vacation rentals and Airbnb offers in Orleans, MA
Orleans, MA
06/25 – 06/30
$846/nighttotal: $4230 (5 )
Private Orleans Getaway Near Bakers Pond & Beaches (2422)
5 2
apartment , Orleans
This Orleans house offers deeded access to Bakers Pond and is located minutes from downtown Orleans' shopping and dining. This 2090 sq ft home accommodates 8 guests with 5 bedrooms and 3 bathrooms, featuring a sunroom, a large deck, and driveway parking for 4 cars.
9.8 9 reviews
Orleans, MA
06/25 – 06/30
$502/nighttotal: $2510 (5 )
Relax And Refresh In Eastham
1 2
apartment , Eastham
This Eastham condo offers a prime location, just a 5-minute drive to First Encounter Beach and a 10-minute drive to Coast Guard Beach. This newly available coastal retreat features 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests with a king bed, queen bed, and loft space, boasting amenities like air conditioning, internet, a dishwasher, and parking.
9.2 11 reviews
Orleans, MA
07/11 – 07/15
$1077/nighttotal: $4308 (4 )
The Alpine/walk To Beach For 2 Or More!
3 3
apartment , Eastham
This Eastham vacation rental, located 176 yards from Thumpertown Beach and near the Cape Cod Rail Trail, offers easy access to Nauset Light Beach, Salt Pond Visitor Center, the Eastham Windmill, and First Encounter Beach. This 1140-square-foot home features four bedrooms, two bathrooms, sleeps twelve (two to eight adults plus four children), and includes a game room with pool and poker tables, a bocce court, grills, Smart TVs, and strong Wi-Fi.
Orleans, MA
07/11 – 07/15
$529/nighttotal: $2116 (4 )
Wellfeet Retreat
3 3
apartment , Eastham
This 3-bedroom, 2-bathroom house in Wellfleet is located minutes from Cahoon Hollow Beach, bayside waters, downtown Wellfleet restaurants and galleries, and the Wellfleet Drive-In Theater. This pet-friendly rental accommodates up to 6 guests and features a fully outfitted kitchen, air conditioning, a garden with a grill and fire pit, and an in-home washer and dryer.
8.4 41 reviews
Orleans, MA
07/06 – 07/10
$389/nighttotal: $1556 (4 )
Comfy Cabin With Deck, Firepit, & Bike Path Access - Walk To Nauset Light Beach
2 3
apartment , Eastham
This Eastham vacation rental is located two miles north of town hall, offering seclusion on a spacious property near the Atlantic Ocean, a bike path, and Nauset Light Beach. This 690 sq ft dwelling accommodates up to eight guests with two bedrooms and one bathroom, featuring central air conditioning, WiFi, a full kitchen, a private deck, outdoor shower, and firepit.
Orleans, MA
07/11 – 07/15
$822/nighttotal: $3288 (4 )
Screened Porch Overlooking Marsh, Spacious Yard, Patio, Fire Pit, And Close To Beach
2 3
cottage , Eastham
This vacation rental, a cottage in North Eastham, is located 5 miles from South Sunken Meadow Beach and close to the Cape Cod National Seashore. This 700 square foot dwelling accommodates up to 4 guests in 2 bedrooms and features 2 bathrooms, air conditioning, a full kitchen, and on-site laundry, with opportunities for birdwatching and kayaking nearby.
9.4 8 reviews
Orleans, MA
06/25 – 06/30
$531/nighttotal: $2655 (5 )
Spacious Harwich Haven Near Round Cove (1116)
3 2
apartment , Harwich
This 3-bedroom, 2-bathroom house in Harwich is located on a quiet cul-de-sac, 0.5 miles from Round Cove on Pleasant Bay, offering convenient access to Chatham and Orleans. This rental accommodates up to 6 guests and features a well-equipped kitchen, air conditioning, a garden, parking, and is 800 meters from Round Cove, with opportunities for sailing, surfing, and fishing nearby.
9.8 298 reviews
Orleans, MA
07/06 – 07/10
$343/nighttotal: $1372 (4 )
The Secret Garden
1 3
apartment , Harwich
This Harwich garden apartment, a mile from Pleasant Bay, Eastward Ho! Golf Course, and the Wequassett Inn, offers easy access to shopping and restaurants. The one-bedroom unit sleeps four with a queen bed, queen pull-out sofa, full kitchen, Wi-Fi, and parking for two cars, plus access to outdoor showers and gardens.
9.8 111 reviews
Orleans, MA
06/25 – 06/30
$459/nighttotal: $2295 (5 )
Cozy Cape Condo Minutes From Brewster Beaches
1 2
apartment , Brewster
This Brewster condo, located on the Ocean Edge Resort Golf Course, offers easy access to Breakwater Beach and Crosby Landing Beach, plus proximity to restaurants like The Brewster Fish House. The 2-bedroom, 2-bathroom unit sleeps 6, features a fully equipped kitchen, patio overlooking the golf course, beach gear, and a 55-inch 4K Samsung TV with streaming services.
10 49 reviews
Orleans, MA
07/06 – 07/10
$342/nighttotal: $1368 (4 )
Bright & Cozy With Patio, Grill Near Beach & Golf
1 3
house , Brewster
This Brewster guesthouse, near Nickerson State Park, offers easy access to Jackknife Beach (9 minutes), Wequassett Resort (8 minutes), and downtown Brewster (7 minutes). The one-bedroom, one-bathroom rental sleeps three, features a well-equipped kitchenette, in-unit laundry, a shared patio with grill, and a comfortable living area with a smart TV; keypad entry ensures convenient access.
Orleans, MA
06/25 – 06/30
$522/nighttotal: $2610 (5 )
Relaxing Eastham Retreat With Waterfront Views
1 2
house , Eastham
This Eastham cottage offers proximity to coastal attractions, located 1.9 miles from South Orleans Beach and 5.2 miles from Nauset Lighthouse. This pet-friendly rental accommodates up to 7 guests and features a fireplace, air conditioning, and a kitchen equipped with a microwave and refrigerator.
9.7 33 reviews
Orleans, MA
07/06 – 07/10
$514/nighttotal: $2056 (4 )
Pet-friendly Cape Escape 6 Min To Beach
1 3
apartment , Harwich
This Harwich vacation rental is located just 2.6 miles from Red River Beach and close to shops and restaurants. It boasts excellent user, location, and cleanliness ratings. This two-bedroom home comfortably sleeps five guests and features a large deck with a gas grill, patio furniture, and an outdoor shower. The fully equipped kitchen includes a fridge, freezer, microwave, and washer and dryer, and the property also has parking, air conditioning, and Wi-Fi.
Best Orleans, MA vacation rentals with a balcony
9.6 17 reviews
Orleans, MA
06/25 – 06/30
$817/nighttotal: $4085 (5 )
Beach & Town Walkable:family Friendly Cape Getaway
4 2
apartment , Eastham
This Eastham vacation home is located within 1-2 miles of Campground Beach and Thumpertown Beach on Cape Cod. This four-bedroom, four-bathroom house sleeps eight guests and features a fully equipped kitchen, free Wi-Fi, a private balcony, and outdoor amenities including a garden and grills; limited housekeeping is available.
This Brewster vacation home, located on Chilton Lane, is 1.3 miles from Ellis Landing Beach and 15 miles from Cape Cod Gateway Airport. The 940-square-foot house features two bedrooms, two bathrooms, and accommodates up to nine guests, offering a private garden, swimming pool, jacuzzi, tennis court, and on-site restaurant and bar.
10 4 reviews
Orleans, MA
06/25 – 06/30
$1038/nighttotal: $5190 (5 )
Charming Retreat Near The Ocean With W/d, Games, & Trails
5 2
apartment , Eastham
This Eastham vacation home is located adjacent to the Cape Cod National Seashore, a short walk from the beach and the Cape Cod Rail Trail. This spacious 2050 sq ft residence accommodates up to 10 guests with 5 bedrooms and 4 bathrooms, offering a screened porch, outdoor games, a grill, and in-room air conditioning or ceiling fans.
Guest-Favorite Family Vacation Rentals in Orleans, MA
These family-friendly vacation rentals in Orleans, MA offer plenty of room to spread out near local beaches.
10 46 reviews
Orleans, MA
07/06 – 07/10
$1120/nighttotal: $4480 (4 )
2021 Construction 3br 3ba, Close To Bike Trail & Beaches. Central Ac Firepit
3 3
apartment , Eastham
This vacation rental in Eastham is located just a short distance from the Cape Cod National Seashore and within 2 kilometers of the Edward Penniman House and Barn. It's a fantastic choice for families or groups of friends looking for a relaxing getaway in a beautiful location. This property has received excellent user ratings, so you can be sure it's a comfortable and well-maintained place to stay. The house has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 6 guests. Enjoy the beautiful weather with a garden, barbecue grills, and a patio, or relax indoors with a fireplace and free Wi-Fi.
9.9 103 reviews
Orleans, MA
07/06 – 07/10
$797/nighttotal: $3188 (4 )
Sleeps 2-8/soaking Tub/firepit~burrows
3 3
apartment , Eastham
This Eastham vacation rental is located less than two miles from the Three Sisters Lighthouses and offers easy access to Nauset Light Beach and Cape Cod beaches. The 1300-square-foot house features three bedrooms, two bathrooms, sleeps eight guests, and includes amenities such as a fully equipped kitchen, Wi-Fi, air conditioning, a patio, and a fireplace.
10 26 reviews
Orleans, MA
07/11 – 07/15
$913/nighttotal: $3652 (4 )
Townhouse At Ocean Edge 2b/2b + Loft
2 3
apartment , Brewster
This Brewster townhouse, a 10-minute drive from the beach, offers access to Ocean Edge Resort amenities for an additional fee. The newly remodeled two-story unit features two bedrooms, two bathrooms, a loft with a convenient workspace, a fully equipped kitchen with dishwasher, in-unit laundry, and a private patio with grill; it comfortably sleeps six guests.
9.2 26 reviews
Orleans, MA
07/06 – 07/10
$410/nighttotal: $1640 (4 )
Cozy Cape Cottage
1 3
cottage , Brewster
This Brewster cottage rental is conveniently located less than 2 kilometers from Nickerson State Park, Linnell Landing Beach, and Ocean Edge Golf Club, offering easy access to Cape Cod's beaches and attractions. This 500-square-foot vacation home features two bedrooms, one bathroom, and accommodates three guests, complete with a fully equipped kitchen, air conditioning, a patio, and on-site parking.
Frequently Asked Questions about vacation rentals in Orleans, MA
The best walking and cycling route in Orleans is the Cape Cod Rail Trail, which runs for 22 miles along the old railroad line. You can also explore the scenic walking trails at the Nickerson State Park or take a leisurely stroll along the Orleans town center.
What are the best Airbnb and vacation rentals in Orleans, MA?
Orleans is a great place for outdoor activities. You can go swimming, sunbathing, or surfing at Nauset Beach. You can also go kayaking or canoeing on the Pleasant Bay or go fishing in the surrounding waters. If you're looking for something more adventurous, you can try kitesurfing or windsurfing on the bay.
Orleans is ideally located on Cape Cod, so you can easily visit nearby towns like Chatham, Harwich Port, and Dennis. You can also take a short drive to Provincetown, the northernmost town on Cape Cod, or to Hyannis, the main transportation hub for the Cape.
What are the best vacation rentals with a pool in Orleans, MA?
Vacation rentals in Orleans typically offer a range of amenities, including kitchens, laundry facilities, Wi-Fi, and outdoor spaces like patios or decks. Some rentals may also have swimming pools, hot tubs, or fireplaces.
What are the best rentals for families and kids in Orleans, MA?
The best time to visit Orleans is during the summer months, from June to August, when the weather is warm and sunny. However, if you're looking for a more peaceful experience, you can visit during the shoulder seasons, spring or fall, when the crowds are smaller and the prices are lower.
What are the best rentals or Airbnbs with a jacuzzi in Orleans, MA?
Orleans is known for its fresh seafood, so you'll find plenty of restaurants serving up lobster rolls, clam chowder, and other seafood dishes. You can also try local specialties like Cape Cod cranberry sauce and Cape Cod oysters.
Destinations nearby
Best Orleans, MA vacation rentals with parking
Orleans, MA
07/11 – 07/15
$1078/nighttotal: $4312 (4 )
Peaceful Stay With Town Cove Access
3 3
house , Eastham
This Eastham vacation rental offers direct access to Town Cove and is located 4.8 miles from Nauset Lighthouse and 6 miles from Wellfleet Bay Wildlife Sanctuary. This 1770 square foot house accommodates up to 11 guests with 3 bedrooms and 2 bathrooms, featuring air conditioning, free WiFi, a full kitchen with a dishwasher, and outdoor dining.
9.3 348 reviews
Orleans, MA
07/11 – 07/15
$2070/nighttotal: $8280 (4 )
Wequassett Resort And Golf Club
1 3
resort , Harwich
The Wequassett Resort And Golf Club is located in Harwich, a short drive from the town center and the Cape Cod National Golf Center. This resort has received excellent ratings for its location, user experience, and cleanliness. The resort has spacious rooms with sitting areas and private decks or patios. Guests can enjoy a variety of amenities, including a swimming pool, hot tub, tennis court, fitness center, and restaurant, as well as a golf course and spa.
8.3 2767 reviews
Orleans, MA
06/25 – 06/30
$903/nighttotal: $4515 (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. The resort has excellent ratings for location, cleanliness, and overall experience. The resort offers spacious villas with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a private beach, indoor and outdoor pools, a golf course, tennis courts, a kids' club, multiple dining options, and a fitness center.
9.4 57 reviews
Orleans, MA
07/06 – 07/10
$1249/nighttotal: $4996 (4 )
5 Bedrooms Ocean View Estate Overlooking Cape Cod Bay
5 3
apartment , Orleans
This Orleans vacation home, located at the end of a cul-de-sac in an exclusive neighborhood, is ¾ mile from Orleans town center, Skaket Beach, and a bike path, and a short walk from Rock Harbor. This 3,800-square-foot waterfront estate boasts five bedrooms, four bathrooms, and sleeps twelve, featuring a private orchard, gazebo, kayak access to the beach, and a separate downstairs apartment with kitchenette.
Check Out Vacation Rentals with a Pool in Orleans, MA
A vacation rental with a pool in Orleans, MA is the ideal way to complement your daily coastal adventures.
10 1 review
Orleans, MA
07/06 – 07/10
$623/nighttotal: $2492 (4 )
Peaceful Retreat On Chilton Lane
2 3
apartment , Brewster
This Brewster apartment rental is conveniently located near Cape Cod beaches and attractions such as the Cape Cod Inflatable Park, offering easy access to other Cape Cod destinations. This 940-square-foot condo boasts two bedrooms, two bathrooms, sleeps five, and includes amenities such as a fully equipped kitchen, free Wi-Fi, a balcony, an on-site water park, indoor pool, and hot tub.
9.1 21 reviews
Orleans, MA
07/11 – 07/15
$2260/nighttotal: $9040 (4 )
Ocean Edge, Bay Pines Villa Two Bedroom
2 3
house , Brewster
The Presidential Bay Villa is located in the Ocean Edge Resort, directly behind the historic Mansion in Brewster, a short walk from the resort's private beach. This two-bedroom, 1,200 square foot villa offers a king-size bed in the master bedroom, a queen-size bed in the second bedroom, a pull-out sofa, a fully equipped kitchen, two bathrooms, a private balcony, and daily housekeeping service.
9.6 23 reviews
Orleans, MA
07/06 – 07/10
$1541/nighttotal: $6164 (4 )
Exceptional Mid-cape Oasis With Many Amenities!
4 3
apartment , Harwich
This Harwich rental is located in central Cape Cod, just minutes from a pond or bay for swimming and a short drive from many Cape beaches. It has excellent user, location, and cleanliness ratings. This four-bedroom, three-bathroom home comfortably sleeps eight guests. The home offers a fully fenced yard, a seasonal swimming pool, a hot tub, a fireplace, a dedicated loft office with wifi, plenty of outdoor lounging space, a well-equipped kitchen, and a master bathroom with an indoor spa.
Ocean Edge Resort offers a second-floor, 2-bedroom, 2-bathroom condo in Brewster, Massachusetts, with excellent user, location, and cleanliness ratings. This end unit has a spacious balcony with golf course views and is just minutes away from Brewster Bay Beaches. The condo comfortably accommodates up to 6 guests and features a fully equipped kitchen, cozy dining room, and master bedroom with an en suite bathroom. Guests can enjoy access to pools, gyms, tennis courts, and resort activities through Ocean Edge Resort Amenities. The condo also includes beach chairs, an umbrella, smart TVs, internet, DVDs, books, and family games for entertainment.
Search Coastal Vacation Rentals near Orleans, MA
Discover charming seaside vacation rentals in Orleans, MA near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
Orleans, MA
06/25 – 06/30
$458/nighttotal: $2290 (5 )
Serene Retreat With Cove Views
1 2
house , Eastham
Orleans, MA
06/25 – 06/30
$1281/nighttotal: $6405 (5 )
Nan's Beach House
2 2
house , Eastham
Orleans, MA
07/11 – 07/15
$468/nighttotal: $1872 (4 )
121 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests
2 3
cottage , Eastham
Orleans, MA
06/25 – 06/30
$379/nighttotal: $1895 (5 )
Serene Retreat With Cove Views
1 2
apartment , Eastham
Discover 5-Star Vacation Rentals in Orleans, MA
Premium waterfront rentals in Orleans, MA combine upscale design with refined service for a truly superior getaway.
9.4 24 reviews
Orleans, MA
06/25 – 06/30
$669/nighttotal: $3345 (5 )
Areys Pond Point
4 2
house , Orleans
Best Vacation Rentals with a Steam Room in Orleans, MA
Elevate your wellness routine with a vacation rental featuring a sauna in Orleans, MA , ideal for a restorative end to your day.
