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Orleans, MA accommodations
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774 Lodgings in Orleans, MA

Popular Lodgings with a Pool in Orleans, MA

Choosing a lodging in Orleans, MA with a pool means you’ll always have a swimming option to complement a day by the water.

Charming 2nd-floor Retreat With Balcony View - Orleans, MA
9.3 37 reviews
Orleans, MA
08/24 – 08/26
$648/nighttotal: $1296 (2 )

Charming 2nd-floor Retreat With Balcony View

2 4
apartment , Brewster
This Brewster apartment rental, located within the Ocean Edge Resort Golf Course, is 1.4 miles from Ellis Landing Beach, 18 miles from Cape Cod National Seashore, and 32 miles from Provincetown.
The two-bedroom, two-bathroom condo sleeps six, features an open-concept kitchen and living area, a swimming pool, jacuzzi, fitness center, and includes free parking and a damage waiver; resort amenities (amenities pass required) such as tennis and pickleball courts are also available.
Peaceful Retreat On Chilton Lane - Orleans, MA
Orleans, MA
08/03 – 08/07
$644/nighttotal: $2576 (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.
Lovely Home W/free Wifi/spacious Patio/spiral Staircase - Near Shops/restaurants - Orleans, MA
8.8 21 reviews
Orleans, MA
08/24 – 08/26
$589/nighttotal: $1178 (2 )

Lovely Home W/free Wifi/spacious Patio/spiral Staircase - Near Shops/restaurants

1 4
apartment , Brewster
This Brewster vacation rental, located 15 miles from Chatham, offers convenient access to Cape Cod Beaches, Cape Cod National Seashore, the Cape Cod Museum of Natural History, and Sheep Pond Woodlands Trail.
This 1070 sq ft, family-friendly apartment sleeps 6 and features a full kitchen, air conditioning, a swimming pool, jacuzzi, spa, and a private patio with a gas grill, with optional Ocean Edge pool/sports club passes available.
Cape Cod Oasis: Heated Salt Water Pool, Game Room, Bike Path! - Orleans, MA
10 12 reviews
Orleans, MA
08/24 – 08/26
$2132/nighttotal: $4264 (2 )

Cape Cod Oasis: Heated Salt Water Pool, Game Room, Bike Path!

4 4
apartment , Eastham
This Eastham apartment is conveniently located just a short distance from Great Pond and Coast Guard Beach, offering easy access to the area's natural beauty and attractions. With excellent user ratings, this property is a popular choice for travelers seeking a comfortable and enjoyable stay. This spacious vacation rental boasts 4 bedrooms and 3 bathrooms, accommodating up to 8 guests, and features a private heated saltwater pool, a large backyard deck with a gas grill and pizza oven, and a finished basement with entertainment options for all ages.

Best family friendly Orleans, MA lodging

Among the 774 accommodations in Orleans, MA, here are the 4 best for families

209 M² House ∙ 4 Bedrooms ∙ 8 Guests - Orleans, MA
8.0 1 review
Orleans, MA
06/25 – 06/30
$659/nighttotal: $3295 (5 )

209 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 2
house , Eastham
This Eastham, Cape Cod home is located less than a mile from Thumpertown Beach and a short drive from Provincetown.
This 2,240-square-foot house features four bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, multiple living areas with smart TVs, a deck with a BBQ, a yard with a fire pit, and family-friendly amenities.
Cape Cod Villa Pond Front Vacation Home, Retreat, Spa, Venue, Film Location - Orleans, MA
10 6 reviews
Orleans, MA
08/24 – 08/26
$1683/nighttotal: $3366 (2 )

Cape Cod Villa Pond Front Vacation Home, Retreat, Spa, Venue, Film Location

5 4
house , Harwich
This Harwich lakefront villa is located within three miles of Nickerson State Park, Adventure Chatham, and two golf courses—Captains Golf Course and Captain's Cove Golf Course.
This five-bedroom, two-bathroom home sleeps eight guests and boasts a spa, game room, fully equipped kitchen, outdoor barbecue grills, and a terrace overlooking the lake, offering easy access to water activities.
Family Friendly Home, Walk To Beach, Central Ac - Orleans, MA
9.8 9 reviews
Orleans, MA
09/02 – 09/10
$439/nighttotal: $3512 (8 )

Family Friendly Home, Walk To Beach, Central Ac

3 4
apartment , Harwich
This charming Cape Cod home is located just steps from a 27-acre swimming pond and an 8-minute drive from the ocean, offering a peaceful retreat close to the beach. Guests consistently rate this property "excellent" for its amenities and location.
The house has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 7 guests. Enjoy amenities like a fully equipped kitchen, a private yard with a deck, and a peaceful pondside setting perfect for swimming, kayaking, or simply relaxing by the water.
Antique Home With Cape Cod Charm - Orleans, MA
8.7 135 reviews
Orleans, MA
08/24 – 08/26
$567/nighttotal: $1134 (2 )

Antique Home With Cape Cod Charm

3 4
apartment , Brewster
This Brewster house, perfect for families, offers easy access to Brewster's beaches and attractions, though its precise location within Brewster is unspecified.
The three-bedroom home, sleeping up to eight with two futons, includes a full kitchen with fridge, microwave, and dishwasher, a garden, ample parking for five cars, laundry facilities, and beach toys—guests supply their own linens.

Frequently Asked Questions about accommodations in Orleans, MA

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Best Orleans, MA accommodation with a balcony

Perfectly Private Location W/deeded Beach Access! - Orleans, MA
9.8 9 reviews
Orleans, MA
08/24 – 08/26
$1102/nighttotal: $2204 (2 )

Perfectly Private Location W/deeded Beach Access!

3 4
apartment , Orleans
This Orleans seaside vacation home boasts stunning ocean views and is conveniently located 2.7 miles from the Orleans Bowling Center and 2.9 miles from the Jonathan Young Windmill, with easy access to Cape Cod Beaches and Rock Harbor Beach within 6 miles.
This 2490-square-foot property features three bedrooms, four bathrooms, and accommodates up to six guests, offering a fully equipped kitchen, in-house laundry, a private balcony, and a garden with barbecue grills.
Stylish Orleans Home With Spacious Deck - Near Bay & Ocean Beach - Orleans, MA
Orleans, MA
09/02 – 09/10
$564/nighttotal: $4512 (8 )

Stylish Orleans Home With Spacious Deck - Near Bay & Ocean Beach

4 4
apartment , Orleans
This Orleans rental is located next to a wetland preserve, under 2 miles from Skakket Beach and 3 miles from Nauset Beach, offering convenient access to local shopping and dining in downtown Orleans.
This 1920 square foot, family-friendly house accommodates up to 8 guests with 4 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a spacious deck, and a garden on a 1.5-acre property.
Book Eastham, Plenty Of Room For Entire Family! - Orleans, MA
9.6 11 reviews
Orleans, MA
08/03 – 08/07
$1021/nighttotal: $4084 (4 )

Book Eastham, Plenty Of Room For Entire Family!

3 3
apartment , Eastham
This three-bedroom house in Eastham is located about one mile from Nauset Light Beach and near bayside beaches with tide pools, offering a private and quiet residential setting.
This 1800-square-foot rental accommodates up to six guests with a fully equipped kitchen, separate entertainment area, outdoor shower, and parking for four cars, all within a peaceful neighborhood.
Guest House Ocean Whisper - Orleans, MA
9.7 4 reviews
Orleans, MA
09/02 – 09/10
$1123/nighttotal: $8984 (8 )

Guest House Ocean Whisper

4 4
house , Harwich
Guest House Ocean Whisper is a beachfront property in Harwich, just 12 miles from Nauset Lighthouse and 19 miles from Wellfleet Bay Wildlife Sanctuary. The property boasts excellent user, location, and cleanliness ratings, ensuring a pleasant stay.
The house offers 3 bedrooms and 1 bathroom, spanning 1210 square feet and accommodating up to 13 guests. Enjoy features like a private balcony, a fully equipped kitchen, air conditioning, a garden, parking, and a shared kitchen and luggage storage area for added convenience.

Best Orleans, MA accommodation with a kitchen

Cozy Condo With Golf Course View, Balcony, W/d, Ac, & Games - Orleans, MA
9.0 10 reviews
Orleans, MA
08/24 – 08/26
$424/nighttotal: $848 (2 )

Cozy Condo With Golf Course View, Balcony, W/d, Ac, & Games

1 4
apartment , Brewster
This condo is located in the Ocean Edge Community in Brewster, MA, offering tranquil golf course views and a short drive to Cape Cod Beaches and the Cape Cod National Seashore.
This 580 square foot unit accommodates up to four guests with a full-size bed and a full-size Murphy bed, featuring a galley kitchen with a washer and dryer, and access to amenities at the Spa at Ocean Edge.
The Secret Garden - Orleans, MA
9.8 297 reviews
Orleans, MA
08/24 – 08/26
$472/nighttotal: $944 (2 )

The Secret Garden

1 4
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.
Dog-friendly Forest Cottage With Firepit & Great D - Orleans, MA
8.5 8 reviews
Orleans, MA
08/24 – 08/26
$654/nighttotal: $1308 (2 )

Dog-friendly Forest Cottage With Firepit & Great D

2 4
apartment , Eastham
This Eastham cottage, located on the tranquil north side, is a half-mile from Thumpertown Beach and within one mile of the Cape Cod Rail Trail and Route 6 restaurants.
This pet-friendly (one dog up to 50 lbs) house boasts two bedrooms, one bathroom, sleeps seven, and features a large deck with a gas grill, firepit, and outdoor shower, plus a modern kitchen with stainless steel appliances and high-speed WiFi.
West-facing Pure Waterfront Home In Orleans, Overl - Orleans, MA
9.0 21 reviews
Orleans, MA
06/25 – 06/30
$510/nighttotal: $2550 (5 )

West-facing Pure Waterfront Home In Orleans, Overl

4 2
apartment , Orleans
This Orleans vacation home boasts 2+ waterfront acres with Arey's Pond access, situated four miles from Nauset and Skaket Beaches and within one mile of two freshwater swimming lakes.
This four-bedroom, two-bathroom house sleeps eight, features a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, free parking for four cars, and offers extraordinary privacy with access to 11+ acres of conservation land for nature walks.
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