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.

0 of 0 items showing

1 of 3 pages

Guest favorite

A serene swimming pool is surrounded by tall greenery, offering a tranquil escape. The crystal-clear water reflects sunlight, inviting relaxation. A decorative statue is visible in the background, enhancing the peaceful atmosphere of the outdoor space.

Apartment in Northampton

4.97 out of 5 average rating, 361 reviews

1880s sun-bathed beauty in best downtown location

Sun-drenched, recently renovated 2nd floor apartment in gracious 4-family Victorian home, steps from Northampton's vibrant downtown. Wonderful open living/dining/kitchen space with new stainless-steel appliances, butcher block counters, wood floors, lots of seating & 42" HDTV. Master BR with queen bed, small 2nd BR with double bed, pull-down sofa in living room. Comfy high-end mattresses. New, small-ish bathroom with shower and tiled floor. Washer and dryer in basement (shared with another apt).

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

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.

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, 39 reviews

Calm Post+Beam Retreat

Escape into our airy, light-filled, modern, cabin. Built with wood milled right here, this serene retreat has lovely sunset views. 700 sqf detached cabin. Sleeping + office loft, 2nd queen sleeper, wood-burning stove, digital thermostat, wifi, 55” TV with Netflix, ample parking. Summer dips in the pool. North Amherst is 10 min from Amherst center, UMASS, Amherst College; 27 min to Smith College. **To access the 2nd floor office, you need to step over a beam. 1-step to the front door.

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, 223 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!

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

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

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, 142 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.

Home in Amherst

5 out of 5 average rating, 8 reviews

Stay in Robert Frost's beautiful house

From 1931 to 1938, Robert Frost lived in this gracious 1874 house, located on a quiet, lovely Amherst street a short walk from town, Amherst College, and UMass. The house can be yours for a country getaway, family get-together, or reunion/graduation weekend. High-ceilinged, private, full of remarkable details, and surrounded by beautiful old trees, this is a piece of Amherst history that is ready for your convivial group.

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

Peaceful log cabin on an 8 acre property. Truly a gem to enjoy: a quiet, relaxing, cozy, sunlit cabin with a vaulted ceiling. Beautiful gardens, warm electric fireplace, and steps away from Atkins Reservoir and hiking trails. You will feel secluded but close to local attractions. Umass only 7 minutes away and close to Amherst College, Hampshire College, Smith College, and Mount Holyoke as well.

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, 214 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. Just 5 min to I-91 and Pike, 15 min to Northampton.