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Holiday rentals with a pool in Massachusetts

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Massachusetts

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
An outdoor lounge area features a circular table surrounded by curved sofas adorned with cushions. Soft curtains frame the space, while potted flowers add vibrant color. Natural light filters through the overhead structure, creating a relaxed atmosphere for gatherings.
Home in Worcester

Gather, Cook & Unwind, 3BR, Fireplace

A private resort — without leaving Worcester. Heated pool, fire table, garden courtyard … your own enclosed escape. ★ "Tania’s place was much more than a place….it was a full on fabulous experience." 🏊Heated Pool (to 81F) 🌿 Courtyard w. lounge + garden 🔥Patio w/ Zen fire table* 🍽️ Natural gas + charcoal grills 💧 Reverse osmosis water filter 66” smart TV projector ❄️ Central air conditioning 🔥Indoor gas fireplace 📶300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.

FamilyValueComfort

4.97 out of 5 average rating, 130 reviews
Guest favourite
Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

Waterfront retreat with private beach access, panoramic marsh views, and unforgettable sunsets. Designed for families and groups looking to relax, reconnect, and enjoy the best of Plum Island living. Enjoy the private pool (open seasonally), expansive outdoor living spaces, firepit lounge, and peaceful wildlife views directly from the property. Spend your days walking the island, to local beaches and restaurants, or simply unwinding by the water. Inside, the home features a modern kitchen, was

ValueFamilyBeach

4.93 out of 5 average rating, 140 reviews
Guest favourite
A spacious yard is surrounded by tall trees, showcasing a playground with a slide and swings. A garden area is interspersed with colorful flowers and is set against the backdrop of lush greenery. A trampoline is visible in the distance, along with a greenhouse.
Farm stay in Rutland

Farm Living

We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, donkeys, peacocks, emu, rabbits, dogs, chickens, ducks and wildlife strolling now and then. There’s opportunity to interact with the animals. Pack n play available for little ones upon request and another twin fold up bed. We truly want all of our guest to enjoy all the farm has to offer and enjoy the peacefulness. Please inquire about kayak rentals. We also have a game room available to rent. See photos

ValueLocationWi-Fi

4.95 out of 5 average rating, 423 reviews
Top Guest favourite
Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

ValueLocationCheck-in

4.99 out of 5 average rating, 102 reviews
Top Guest favourite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 4 futons/mattresses. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families. Great pool and hot tub!

ValueLocationBackyard

4.95 out of 5 average rating, 179 reviews
Guest favourite
A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.
Apartment in Brighton

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

FamilyValueGetting around

4.96 out of 5 average rating, 159 reviews
Top Guest favourite
A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.
Farm stay in Hopkinton

1790 Stone Manor Farm

This historic New England farm and home is on almost 7 acres of land with mature gardens and places to hike, it is a warm and inviting place to spend lovely summer days by the pool and enjoy warm nights by the fire in the fall and winter. Kitchen and bathrooms all renovated. Located centrally in Ma- 90/495 interchange. Located 45 minutes from Boston, beach, history, mountains, lakes, & NE sports. This home is in historic Hopkinton, where the Boston Marathon starts, center of MA.

LocationFamilyDecor

4.96 out of 5 average rating, 166 reviews
Superhost
A serene pool area is surrounded by lush gardens, featuring vibrant flowers in planters. A pool house is visible in the background, framed by greenery. The clear water of the pool reflects the surrounding natural beauty, inviting relaxation and enjoyment.
Home in Plymouth

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & a fire pit. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod.

LocationValueWi-Fi

4.9 out of 5 average rating, 198 reviews
Guest favourite
A clear, inviting pool is surrounded by lush greenery and mature trees, providing a serene and private atmosphere. The pool features a gently curving shape and is bordered by textured stone paving, with sunlight reflecting off the water's surface.
Apartment in Holyoke

NE Historical Mansion-pets and pet lovers welcome

Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

FamilyLocationLaundry

4.81 out of 5 average rating, 317 reviews
Top Guest favourite
A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.
Home in North Andover

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

ValueLocationLayout

4.95 out of 5 average rating, 184 reviews
Top Guest favourite
A spacious wrap-around porch is shown with comfortable seating, offering panoramic views of the waterfront. The warm glow of sunrise reflects on the water, and a distant bridge is visible under a clear sky. The setting invites relaxation and enjoyment of the serene environment.
Home in Somerset

Beachfront W/ Hot Tub, Sauna, Pool & Panoramic View

Welcome to the Heart of Somerset! Read our reviews & stay a while! Nestled at the very tip of Somerset on a private dead-end road, this coastal waterfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure Marvel at the panoramic views and dramatic colors from Sunrise to Sunset. Grab a kayak, or sit back and relax and let the gentle sea breeze wash your worries away!

LocationValueBarbecue

4.99 out of 5 average rating, 192 reviews
Guest favourite
A spacious bedroom features a large bed adorned with a patterned green and white quilt. Natural light floods the room through multiple windows, highlighting a small desk and ergonomic chair. Soft lighting is provided by sconces on the walls.
Guesthouse in Worcester

Quiet Oasis In The City

Forget your worries in this spacious and serene space. We are right in the city but you'll feel miles away. This two level guest home is surrounded by nature and very relaxing. Two bedrooms and two baths. Two king sized beds. One full bath with oversized tub downstairs. Upstairs bath with standing shower. Full kitchen and coffee and tea. Hot tub is included with BNB. Pool is a separate rental. Message for details.

FamilyLocationAccess

4.82 out of 5 average rating, 115 reviews

Popular amenities for Massachusetts rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
Home in Colrain

The 1770 House

FamilyLocationLaundry

4.9 out of 5 average rating, 143 reviews
Top Guest favourite
The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.
Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

FamilyLocationAir conditioning

4.96 out of 5 average rating, 143 reviews
Top Guest favourite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

LocationFamilyLayout

4.9 out of 5 average rating, 239 reviews
Guest favourite
The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.
Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

LocationFamilyBathroom

4.93 out of 5 average rating, 108 reviews
Superhost
Home in Becket

Berkshires Lodge | Pool, Hot Tub & Fire Pit

FamilyLocationIndoor spaces

4.87 out of 5 average rating, 116 reviews
Top Guest favourite
The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.
Home in Weston

Spacious vacation unit in premium suburban town

LocationValueParks

4.97 out of 5 average rating, 120 reviews
Guest favourite
Home in Wareham

Edgewater Retreat | Oceanfront Home | Heated Pool

FamilyLocationTV

4.91 out of 5 average rating, 104 reviews
Superhost
An indoor pool area features large windows and skylights that allow ample natural light. A tropical plant in a pot is positioned in the foreground. The pool is surrounded by a spacious deck with seating options, providing a relaxed environment for enjoyment.
Home in New Bedford

Poseidon's Palace - 2.0

FamilyValueHeating

4.73 out of 5 average rating, 228 reviews

Condo rentals with a pool

Guest favourite
Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

ValueLocationKitchen

4.97 out of 5 average rating, 179 reviews
Top Guest favourite
An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.
Condo in Brewster

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

ValueLocationOutdoor spaces

5.0 out of 5 average rating, 101 reviews
Guest favourite
A scenic view showcasing the bay with gently rippling waters and distant land on the horizon. The foreground features coastal vegetation, including pines and shrubs, along a wooden pathway leading toward the beach. Nearby, a stop sign indicates road access.
Condo in Provincetown

P-Town Beach Beauty on the Bay. Water View!

LocationValueLayout

4.97 out of 5 average rating, 262 reviews
Top Guest favourite
A spacious living area features a light-colored sofa and a patterned accent chair. A dining table for four and a coffee table are present. Large windows allow natural light, showcasing the balcony view. A ceiling fan provides ventilation, and an air conditioning unit is visible.
Condo in Brewster

Ocean Edge Resort-Pool Access-Golf View-2 bdr/2bth

ValueFamilySleep quality

5.0 out of 5 average rating, 99 reviews
Top Guest favourite
A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.
Condo in Dennis Port

Sea Salt Studio - Steps to Glendon Rd Beach

LocationValueHospitality

4.92 out of 5 average rating, 133 reviews
Guest favourite
A crystal-clear pool is framed by a deck lined with blue lounge chairs. The setting includes landscaped greenery and trees, with two-story buildings in the background providing serene surroundings. The clear blue sky enhances the tranquil atmosphere of this communal outdoor space.
Condo in West Dennis

Mid Cape Cod, 3 Season Haven by Bass River

LocationFamilyIndoor spaces

4.86 out of 5 average rating, 64 reviews
Guest favourite
A wooden sign is displayed on a light-colored wall, featuring the phrase 'Heaven is a little closer by the Beach' in white lettering on a teal background. The sign is framed in a rustic white border, enhancing its coastal charm.
Condo in West Dennis

Hidden Hideaway

LocationFamilyCheck-in

4.87 out of 5 average rating, 69 reviews
Guest favourite
The living area features a light-colored sofa paired with matching armchairs. A small table holds fresh flowers. Soft lighting from lamps creates a comfortable environment. Large sliding doors provide natural light and open to an outdoor patio with a dining set.
Condo in Brewster

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

ValueFamilyAccess

4.96 out of 5 average rating, 99 reviews

Other holiday rentals with a pool

Top Guest favourite
A cozy living area is featured with a brown sofa adorned with patterned cushions. A small coffee table sits on a patterned rug, and a lamp is positioned beside a side table. In the background, the kitchen is visible, showcasing stainless steel appliances and additional cabinetry.
Guest suite in Hubbardston

In-law Apartment, Full Kitchen, Near Mt Wachusetts

FamilyValueParking

4.98 out of 5 average rating, 221 reviews
Top Guest favourite
A spacious exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.
Apartment in Groton

Farmhouse Guest Apartment

ValueLocationCleanliness

5.0 out of 5 average rating, 108 reviews
Guest favourite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury

Country Cottage in the City

LocationValueCheck-in

4.95 out of 5 average rating, 217 reviews
Superhost
Home in Sterling

Pool•1000mbpsWiFi•DeepTub•Fireplace•Full Kitchen

ValueLocationDecor

4.83 out of 5 average rating, 24 reviews
Superhost
Home in Methuen

The Stunning Melita Farms Geodesic Dome Farmhouse

LocationFamilyComfort

4.91 out of 5 average rating, 11 reviews
Guest favourite
Cabin in Bellingham

Rustic Cabin | 25 Min (16 Mi) to Gillette Stadium

LocationFamilyCheck-in

4.92 out of 5 average rating, 79 reviews
Guest favourite
A large, inviting pool is surrounded by a neatly landscaped yard featuring an array of lounge chairs. A wooden cabana is situated nearby, and expansive views of the lake and trees are visible in the background under a clear blue sky.
Home in Winchendon

Amazing Lakefront Home with Pool- Tatum's Place

LocationFamilyWalkability

4.89 out of 5 average rating, 54 reviews
Top Guest favourite
Home in Waltham

Private/Quiet Single Family Home

FamilyValueAccuracy

4.94 out of 5 average rating, 84 reviews

Destinations to explore