Vacation 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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Guest favorite

Bungalow in Easthampton

4.92 out of 5 average rating, 472 reviews

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Guest favorite

Rental unit in Waltham

4.97 out of 5 average rating, 267 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Guest favorite

Rental unit in Winthrop

4.96 out of 5 average rating, 297 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favorite

Home in Somerset

5 out of 5 average rating, 102 reviews

Beachfront W/ HotTub,Sauna, Pool & Panoramic view

Welcome to the Heart of Somerset! 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 of the Braga Bridge, Mt. Hope Bridge & Bay, Bristol, Tiverton Rhode Island & the Fall River cityscape on the horizon. Grab a kayak or relax, soak up the sun & let the gentle sea breeze wash your worries away!

Guest favorite

Rental unit in Northampton

4.98 out of 5 average rating, 283 reviews

Sunny Inspirit Apartment in best downtown location

Two blocks from Main St & steps from Smith College, in the heart of vibrant downtown, this sun-flooded 2br apt/terrace with original 1890s wood floors is in the home of the family behind Northampton's iconic Inspirit Crystals shop. Your 2 south-facing BRs (1 w/sitting area) are drenched in sunlight. A fully equipped eat-in kitchen opens onto a small private terrace with café seating for 2 overlooking tree-shaded Trumbull Rd. Shared outdoor pool, garden w swing, play gym & sandbox for kids' use.

Guest favorite

Home in Plymouth

4.89 out of 5 average rating, 238 reviews

Ocean Side, Amazing View, close to town/beach, Spa

PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF. We only use this listing to fill gaps when the larger listing isn't rented & will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

Guest favorite

Cottage in Marblehead

4.98 out of 5 average rating, 107 reviews

4 Houses from Harbor | Old Town | Pool | Parking

Sitting a mere 4 houses down from the harbor in Old Town Marblehead, this home is a quaint antique cottage with a backyard pool that is surrounded by a beautiful garden — just steps away from The Barnacle Restaurant. Private backyard pool with indoor and outdoor seating. Close to attractions like Fort Sewall, Fort Beach, and local eateries. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

Guest favorite

Rental unit in Winthrop

4.95 out of 5 average rating, 222 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Our saltwater pool is nicely terraced and overlooks stunning ocean views. We are 4 short miles from the city and public transportation is easily accessible; a convenient option into Boston. Winthrop is a welcome relief from the hustle and bustle of the city where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Guest favorite

Guesthouse in Lenox

4.92 out of 5 average rating, 190 reviews

Modern Barn with Loft at House on Golden Hill

Featuring 35 foot cedar ceilings, large windows, and skylights, The Barn is an oversized two-bedroom apartment with loft at House on Golden Hill, a 1790's farmhouse property in Lenox. The Barn is a detached dwelling with large secluded outdoor space and reserved parking for 3 cars. Situated next to the property's river, the barn provides sweeping mountain views and an idyllic Berkshires experience. Centrally located in the Berkshires and minutes from downtown Lenox and Tanglewood.

Guest favorite

Home in Hopkinton

4.94 out of 5 average rating, 145 reviews

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 2 futons and a mattress. 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.

Guest favorite

Rental unit in Northampton

4.99 out of 5 average rating, 103 reviews

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.

Guest favorite

Farm stay in Rutland

4.96 out of 5 average rating, 350 reviews

Farm Living

We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, 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 or replace and enjoy the peacefulness. Please inquire about kayak rentals.