Orleans, MA Vacation rentals & Airbnb

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.

9.6 458 reviews

Orleans, MA

07/06 – 07/10

$467/nighttotal: $1868 (4 )

Pleasant Bay Village Resort

1 3

resort, Chatham

The Pleasant Bay Village Resort is located in Chatham, Massachusetts, just 2.5 miles from the Chatham Railroad Museum and an 8-minute drive from the Chatham Lighthouse. This 4-star resort has received excellent user ratings for its location, cleanliness, and overall experience.
The resort offers spacious rooms with comfortable furnishings, floral décor, cable TV, a fridge, and a work desk. Guests can enjoy a variety of amenities and activities, including a seasonal outdoor pool, a hot tub, a game room, a children's playground, ping-pong, laundry facilities, and a restaurant.

Orleans, MA

07/06 – 07/10

$617/nighttotal: $2468 (4 )

Peaceful Retreat On Chilton Lane

2 3

house, Brewster

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

Which walking or cycling routes are the best in Orléans, 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?
Walk To Private Beach - Spacious Peaceful Apartment, Charming Waterfront Lake House On Spring Fed Pilgrim Lake and Highly Rated Cottage In Orleans - Cape Cod are the most popular Airbnb and vacation rentals in Orleans, MA among travelers.
What sports or outdoor activites can visitors enjoy in and around Orléans, 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.
What are the most popular Airbnbs in Orleans, MA?
Among the Airbnbs in Orleans, MA, Charming Waterfront Lake House On Spring Fed Pilgrim Lake, Walk To Private Beach - Spacious Peaceful Apartment and 1 Min Drive To Rock Harbor - 2 Min To Town are the most popular ones.
What other towns or cities can be easily accessed from Orléans, MA?
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?
Stunning Property With Private Heated Pool - Walk To Ocean Beaches - Sleeps 12, 5 Br\/4 Bath W\/heated Pool -2 Miles To Nauset Beach and Luxury 8 Bedroom Home W\/ Pool - 4 Minutes To The Beach are the best vacation rentals with a pool in Orleans, MA.
What amenities are commonly available in vacation rentals in Orléans, 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 rentals for families and kids in Orleans, MA are Walk To Private Beach - Spacious Peaceful Apartment, Charming Waterfront Lake House On Spring Fed Pilgrim Lake and Stunning Property With Private Heated Pool - Walk To Ocean Beaches - Sleeps 12.
What time of year is best to rent a vacation rental Orléans, 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?
The best vacation rentals or Airbnb with a jacuzzi in Orleans, MA are Stunning Property With Private Heated Pool - Walk To Ocean Beaches - Sleeps 12, Large - Charming Cape Cod Home Close To Orleans And Chatham Beaches and Luxury 8 Bedroom Home W\/ Pool - 4 Minutes To The Beach.
What are the local dishes in Orléans, MA region?
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.

9.9 198 reviews

Orleans, MA

07/06 – 07/10

$503/nighttotal: $2012 (4 )

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

1 3

apartment, Brewster

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.

10 102 reviews

Orleans, MA

07/06 – 07/10

$544/nighttotal: $2176 (4 )

Ocean Edge Resort-pool Access-centralac-2 Bdr/2bth

2 3

apartment, Brewster

Search vacation rentals in Orleans, MA from 100+ sites!

Best Vacation rentals and Airbnb offers in Orleans, MA

Private Orleans Getaway Near Bakers Pond & Beaches (2422)

Relax And Refresh In Eastham

The Alpine/walk To Beach For 2 Or More!

Wellfeet Retreat

Comfy Cabin With Deck, Firepit, & Bike Path Access - Walk To Nauset Light Beach

Screened Porch Overlooking Marsh, Spacious Yard, Patio, Fire Pit, And Close To Beach

Spacious Harwich Haven Near Round Cove (1116)

The Secret Garden

Cozy Cape Condo Minutes From Brewster Beaches

Bright & Cozy With Patio, Grill Near Beach & Golf

Relaxing Eastham Retreat With Waterfront Views

Pet-friendly Cape Escape 6 Min To Beach

Beach & Town Walkable:family Friendly Cape Getaway

Pleasant Bay Village Resort

Peaceful Retreat On Chilton Lane

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

2021 Construction 3br 3ba, Close To Bike Trail & Beaches. Central Ac Firepit

Sleeps 2-8/soaking Tub/firepit~burrows

Townhouse At Ocean Edge 2b/2b + Loft

Cozy Cape Cottage

Peaceful Stay With Town Cove Access

Wequassett Resort And Golf Club

The Mansion At Ocean Edge Resort & Golf Club

5 Bedrooms Ocean View Estate Overlooking Cape Cod Bay

Peaceful Retreat On Chilton Lane

Ocean Edge, Bay Pines Villa Two Bedroom

Exceptional Mid-cape Oasis With Many Amenities!

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

Serene Retreat With Cove Views

Nan's Beach House

121 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

Serene Retreat With Cove Views

Areys Pond Point

Ocean Edge Resort-pool Access-centralac-2 Bdr/2bth