Vacation rentals with a pool in Hampshire County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hampshire County

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

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Guest favorite

A circular pool is set within a grassy area, surrounded by lush greenery. A shaded picnic area features a large table beneath a white umbrella. Colorful inflatables are visible on the water's surface, adding a playful touch to the serene outdoor setting.

Bungalow in Easthampton

4.92 out of 5 average rating, 495 reviews

The Creation Station

SpencerRating, 5 stars2 weeks ago

We love the creation station! We stayed for one night and it simply wasn’t enough! What a cool and magical property. Inside is quite a trip. Surround sound for your listening pleasure, huge projection screen for watching tv. Comfortable beds, and the place was well kept up and clean. Outside is magical at night and the hot tub was just perfect after a long day. John was super nice and very helpful. We will certainly be back for some more fun. Highly recommend this place you will not be disappointed. Peace & Love: Spencer and Julie

Top guest favorite

A vibrant swimming pool reflects the blue sky and fluffy clouds above. Lush green hills and colorful flowers can be seen in the background, surrounded by a rustic wooden fence, creating a serene outdoor retreat.

Home in Chesterfield

4.98 out of 5 average rating, 55 reviews

High Field Farm

Christopher WRating, 5 stars6 months ago

Set upon the eastern bluffs of the Berkshire hills, Highfields farm is a stunningly beautiful property with great vistas. The autumn leaves were changing and the crisp clear mornings gave way to comfortably warm days.! The night sky was spectacular without light pollution. We will be back

A spacious outdoor area features a rectangular pool bordered by a wooden fence. A pool slide extends into the water, while lounge chairs and pool equipment are arranged around the deck, all set against a backdrop of a two-story cabin with large windows. Snow gently blankets the ground.

Home in Deerfield

4.8 out of 5 average rating, 221 reviews

Perfectly Polished Deerfield Home 5 min to I-91

GuthrieRating, 5 stars4 weeks ago

From the beginning of this stay until the end, Cindy and Ron were great hosts. We were coming together as a 4-generation family from Vermont, California and Massachusetts to be here for a birth, and we could not have found a better place to stay than this one!

A contemporary guest house sits adjacent to the main home, featuring large windows that invite natural light. The structure is oriented towards a tranquil in-ground pool. Outdoor seating is positioned near the pool, and lush greenery is visible in the surrounding yard.

Guesthouse in Northampton

5 out of 5 average rating, 3 reviews

Newly Constructed Guest House with Pool

JenniferRating, 5 stars6 months ago

I really enjoyed my stay! The location is excellent -- Florence is a lovely small town, and it's only a short drive to Smith College and Northampton. Julie actually came outside to greet us, so I can't speak about the lockbox check in. Her adorable dog Charlie escorted us into the house and hung out with us for a while, which was fantastic -- such a cutie! The guesthouse itself was perfect for our needs -- small and clean, and had everything we needed.

Top guest favorite

A living room is displayed, featuring a comfortable blue couch adorned with patterned pillows. Three framed landscape images are mounted on the wall above a wooden coffee table. Natural light enters through a window with sheer curtains, illuminating a cozy reading nook in the background.

Apartment in Northampton

4.99 out of 5 average rating, 139 reviews

Cozy Haven: Convenience & Charm

PennyRating, 5 stars4 days ago

Beth and Michael's Cozy Haven is so thoughtfully laid out. The apartment has everything needed for a very comfortable and relaxing stay. We made excellent use of their beautifully outfitted kitchen. The really have thought of everything and we had the best time. Thank you.

Top guest favorite

A refreshing pool is surrounded by vibrant flowers and greenery, providing a serene outdoor setting. Lounge chairs are arranged around the pool, inviting relaxation. The pool area is fenced, ensuring privacy and safety for guests.

Guest suite in Amherst

4.96 out of 5 average rating, 294 reviews

Sunlit Clean Amherst Cozy Log Cabin

ChrisRating, 5 stars2 months ago

Such lovely hosts! They went way above and beyond -- even going as far as unnecessarily shoveling all of the snow from my car, as there was significant snow fall overnight. And, for the first time in my life, I left an item behind at an airbnb, and they generously offered to mail it back to me. So grateful!

Guest favorite

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

4.78 out of 5 average rating, 211 reviews

NE Historical Mansion-pets and pet lovers welcome

NoahRating, 5 stars5 days ago

We loved our stay! We were coming out to see family, and this was a great place to stay with toddlers. Very big, with a great common room. The beds were comfy, and basics provided. It's not super decked out for cooking, but accurately described online. Beautiful views- we loved waking up and seeing the landscape. Very cool old house.

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What guests are saying

Light-bathed 3br w porch in best downtown location

4.93 out of 5 average rating, 215 reviews1 month ago

Perfect location for walking downtown and exploring the surrounding areas. The home is inviting, and the couch and beds are very comfortable. Instructions are clear and easy, and Sue has a notebook full of wonderful local recommendations. Our family of four felt very much at home and would definitely return.

Apartment in Northampton

What guests are saying

Pool hot tub pet friendly

4.2 out of 5 average rating, 10 reviews34 months ago

Katie and Mike are fabulous hosts! Katie provided helpful information prior to our arrival. Mike helped us pump up a flat bike tire and gave us great tips on area activities. The apartment was very clean and spacious given its size because it's not cluttered. The bed is very comfortable, and everything in the apartment worked well. The pool is lovely! It's shared with the family, but Mike and Katie were very thoughtful about making it accessible to us when their kids weren't in the pool. The house is set in a quiet, rural setting but only 20 minutes from downtown Northampton. I would definitely recommend this spot to other travelers!

Apartment in Williamsburg

What guests are saying

Wood, sunshine & movies in best downtown location

4.93 out of 5 average rating, 235 reviews1 month ago

This is our third time staying in one of Sue's Northampton properties (a different place each time) and, as always, the apartment was great. It's spacious, comfortable, and thoughtfully appointed. The location is wonderful, with easy walking to everything, and Sue is an excellent host. Highly recommended!

Apartment in Northampton

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Popular amenities for Hampshire County rentals with a pool

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House rentals with a pool

Top guest favorite

Home in Chesterfield

4.98 out of 5 average rating, 55 reviews

High Field Farm

Christopher WRating, 5 stars6 months ago

Set upon the eastern bluffs of the Berkshire hills, Highfields farm is a stunningly beautiful property with great vistas. The autumn leaves were changing and the crisp clear mornings gave way to comfortably warm days.! The night sky was spectacular without light pollution. We will be back

Home in Amherst

5 out of 5 average rating, 8 reviews

Stay in Robert Frost's beautiful house

HilaryRating, 5 stars18 months ago

Lovely home. Everything was as great as we expected. Alexander is a superb host. There was even a great book collection! We look forward to coming back. Thank you Alexander!

Top guest favorite

This living area features a stone fireplace as a focal point alongside large skylights allowing natural light to fill the space. A cozy seating arrangement is present, complemented by a patterned area rug. Large glass doors open to an accessible outdoor deck, enhancing the connection to nature.

Home in Westhampton

5 out of 5 average rating, 20 reviews

Happy Valley getaway

BarbaraRating, 5 stars5 days ago

We had a lovely family Easter weekend - 6 adults, 4 kids. The house was very comfortable and spacious. The kids loved the game room and the giant downstairs television! Great yard too.

Guest favorite

An outdoor dining area features a table and chairs set on a stone patio, alongside a barbecue grill. A heated, in-ground pool is surrounded by comfortable lounge chairs, with shaded umbrellas. Lush greenery and trees provide a private backdrop, enhancing the tranquil environment.

Home in Worthington

5 out of 5 average rating, 6 reviews

Morning Side

RebeccaRating, 5 stars4 months ago

Morning Side is filled with character and charm. The house itself, the furnishings, and even the book collection take you back to 18th century New England. The kitchen and dining area are particularly cozy and inviting. The windows and views are magical, particularly with a good snowfall. The host was very helpful, particularly proactive about preparing the sidewalk and driveway for snowfall, even on Thanksgiving Day!

Guest favorite

Home in Northampton

5 out of 5 average rating, 12 reviews

Sun-drenched 6BR Victorian steps from downtown

HerveRating, 5 stars3 weeks ago

Just What We Needed We had a marvelous trip to Northampton MA and Sue's large Victorian house was perfect for our group's stay. Of course it was clean and comfortable, but in many ways it had more than what we needed, from parking to rooms and other amenities, I was especially pleased to find convenient outlets and USB ports, even by the bed (which is better than some hotels I've stayed at). Sue had a welcoming gift in the kitchen, communicated responsively and helpful with ideas about the area, as our 'home' was truly conveniently located just blocks from the trendy downtown area. An enjoyable stay in a charming city.

Top guest favorite

A serene outdoor pool is surrounded by vibrant greenery and a wooden fence. A covered pavilion is situated nearby, featuring seating options. Natural stone pavers line the pool area, providing easy access, while lush grass enhances the tranquil setting.

Home in Amherst

4.97 out of 5 average rating, 37 reviews

Calm Post+Beam Retreat

DeborahRating, 5 stars1 week ago

My daughter and I were visiting colleges and we booked this home. It’s super cozy and was a wonderful spot to stay. We’d love to stay there again!

Home in Deerfield

4.8 out of 5 average rating, 221 reviews

Perfectly Polished Deerfield Home 5 min to I-91

GuthrieRating, 5 stars4 weeks ago

From the beginning of this stay until the end, Cindy and Ron were great hosts. We were coming together as a 4-generation family from Vermont, California and Massachusetts to be here for a birth, and we could not have found a better place to stay than this one!

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Vacation rentals with a pool in Hampshire County

Top-rated rentals with a pool in Hampshire County

Light-bathed 3br w porch in best downtown location

Sunny Inspirit Apartment in best downtown location

Skylights, art + design in best downtown location

Northampton-area Hot tub Pet Friendly

Luxury w sunny balcony in best downtown location

Pool hot tub pet friendly

Wood, sunshine & movies in best downtown location

Vacation rentals for every style

Popular amenities for Hampshire County rentals with a pool

House rentals with a pool

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