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 charming property is illuminated with colorful lights during the evening. The spacious deck is adorned with festive decorations, and a Christmas tree can be seen through large windows. The surrounding area is dark, emphasizing the warm glow of the lights.

Bungalow in Easthampton

4.92 out of 5 average rating, 530 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

Top guest favorite

A bright and airy living space features a vaulted ceiling with a mounted ceiling fan. Large glass doors open to a balcony, framed by orange curtains. A rustic wooden coffee table sits at the center, surrounded by a leather couch and armchair, with a TV and bookshelf visible.

Apartment in Northampton

4.99 out of 5 average rating, 241 reviews

Skylights, art + design in best downtown location

Elegant spacious sun-drenched 2-bdrm penthouse in 4-family Victorian on tree-lined street in downtown Northampton. Easy walk to Smith campus. Skylights; large tiled bathroom w/ shower, jacuzzi tub, washer/dryer; renovated kitchen with Italian-tiled floor; open floor plan with ample dining area; living area with large leather couch, handmade rustic wood coffee table, lg TV, Yamaha digital piano, cathedral ceiling, and glass doors onto a balcony. Home theatre in master bedroom. Off-street parking.

Guest favorite

A sunlit living space features a black leather chair and a small coffee table. A wooden bookshelf filled with books and decorative items lines the wall, accompanied by wall-mounted art pieces. The room's yellow walls add warmth, while a window provides natural light.

Apartment in Northampton

4.98 out of 5 average rating, 321 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.

Top guest favorite

An aerial view presents High Field Farm set amidst vibrant autumn foliage, with rolling hills stretching into the distance. The classic farmhouse is nestled within expansive grounds, featuring lush greenery and a fenced-in swimming pool, all bathed in soft, natural light.

Home in Chesterfield

4.98 out of 5 average rating, 63 reviews

High Field Farm

Come to High Field Farm to getaway and unwind in a beautiful, classic New England farmhouse. Set on over 500 acres of land, enjoy a spacious, tasteful and pristine country vacation home, lovingly cared for by the same family for over 50 years. The house offers four bedrooms and two full bathrooms, and endless outdoor opportunities like hiking or fly-fishing. You'll enjoy spectacular mountain views in an idyllic and private country setting that will enchant and nourish your heart and soul.

Guest favorite

A living area features a spacious blue sofa with ample cushions, complemented by a wooden coffee table. Large sliding glass doors provide access to a balcony, framed by light curtains that enhance natural light. Two windows on the side allow additional sunlight to fill the room.

Apartment in Northampton

4.9 out of 5 average rating, 211 reviews

Luxury w sunny balcony in best downtown location

Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.

Superhost

A spacious living area is highlighted by a curved sectional sofa facing a media console, featuring a variety of television options. Large windows invite natural light, while warm wooden beams add structural interest to the ceiling.

Home in Deerfield

4.8 out of 5 average rating, 246 reviews

Perfectly Polished Deerfield Home 5 min to I-91

A perfectly polished home, nestled in the Sugarloaf Mountain Range with a view of Mount Toby! This property offers 4 bedrooms and 4 beds. With over 2000 sqft of living space, you will enjoy coming home to wind down after a day at Yankee Candle, hiking, or other event in the beautiful Pioneer Valley. The house has something for everyone, whether it’s streaming your favorite show on Netflix, Hulu or Prime Video or relaxing on the patio deck while the kids enjoy the huge pool and water slide!

Top guest favorite

A modern guest house is visible beside a clear in-ground pool. The structure features dark siding and large windows, with a private patio area decorated with lounge chairs. Surrounding greenery and fencing provide a tranquil outdoor setting, suitable for relaxation.

Guesthouse in Northampton

5 out of 5 average rating, 14 reviews

Newly Constructed Guest House with Pool

200 sf guest house adjacent to our home. Space complete w/ wifi, heat, A/C + ceiling fan. QUEEN size sleeper sofa , full size mattress in sleeping loft, kitchenette w/sink + mini fridge, HALF bath, OUTDOOR shower, private patio and in-ground pool. Outdoor lighting allows for nighttime enjoyment of guest house, pool and enclosed yard. Walking distance to Florence ctr, 2 mi from downtown Northampton. THIS SPACE IS MORE COMFORTABLE FOR 2 PEOPLE - but there is enough sleeping space for 3.

Top guest favorite

Home in Deerfield

5 out of 5 average rating, 5 reviews

Serene South Deerfield Retreat

Discover a quiet escape in the heart of historic South Deerfield, MA. This thoughtfully renovated home blends rustic charm with modern comforts, creating a warm and welcoming space for adult families, couples, or professionals looking to unwind, explore and recharge. Located at the base of Mt Sugarloaf and minutes from Yankee Candle, Treehouse Brewery, Deerfield Academy and the Connecticut River. This cozy retreat offers easy access to some of Western MA most beloved attractions.

Top guest favorite

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

4.96 out of 5 average rating, 118 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

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

4.79 out of 5 average rating, 251 reviews

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.