Holiday rentals with a pool in Hampden County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hampden County

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

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Guest favourite

Bungalow in Easthampton

4.93 out of 5 average rating, 518 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 favourite

Apartment in Northampton

4.99 out of 5 average rating, 226 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.

Superhost

Apartment in Northampton

4.93 out of 5 average rating, 243 reviews

Wood, sunshine & movies in best downtown location

Sun-drenched 1st fl apt in 2-family Victorian, steps from Northampton's vibrant downtown. 2 spacious queen bedrooms, 1 bedroom/study with pull-out king. Pine-paneled kitchen with breakfast bar; open living/dining room; stereo with turntable and vintage record collection; home theater with projector. Private deck. Wood floors throughout apartment. 42" HDTV in master bedroom. Hi-speed Internet. Laundry room in basement with washer/dryer (shared with upstairs apt). Shared heated pool (Mar-Nov).

Superhost

Home in Brimfield

4.88 out of 5 average rating, 76 reviews

Luxury Home * Pool * Fireplace

This private spacious home sits high on a hill, ringed with trees over looking rolling hills and grazing cattle. Step inside, and be instantly captivated by its natural warmth and glowing ambiance. Just 3 hrs from NYC, 1 hr from Boston, 45 mins. from Hartford and 5 mins. from I90 and I84. Features a sprawling New-England styled front porch. Crystal clear pool nestled in cobblestone paths, lush green grass and whimsical flowers. Modern country charm, vaulted ceilings and open floor plan.

Guest favourite

Campsite in Brimfield

4.9 out of 5 average rating, 10 reviews

Cozy Campground Cabin Steps from a Gorgeous Lake

Ammenities include a pool, beach access,bathrooms, a rec hall with weekend activities, and more! Our cabins come equipped with a bunk bed with full mattresses, a kitchenette with mini fridge, coffee maker, and microwave. You will have your own private bathroom with a shower, toilet and sink. Our cabins come equipped with cable and a flat screen TV. our cabins are not fully equipped so you will need to supply your own bedding, toiletries, and anything else you may need during your stay.

Top Guest favourite

Home in Blandford

5 out of 5 average rating, 7 reviews

Whitetail Ridge Acres of The Berkshires

There are so many wonderful things that make our home such a special peaceful getaway. From the fruit trees to the flower gardens to our big beautiful deck full of morning sunshine! We also offer a new swimming pool and a outdoor dining setup with a new grill and lots of space and seating for everyone. We are so close to many of the area's attractions such as Jacob's Pillow (17 mins.) to Tanglewood in Lenox (45 mins.) but still located in a lovely small town on a quiet peaceful road.

Top Guest favourite

Guesthouse in Northampton

5 out of 5 average rating, 10 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.

Home in Longmeadow

Luxury 2 Bedroom Basement Apt

Fully-finished basement (approx. 1700 sq.ft.) including 2 large bedrooms & a bathroom. The Family Room has a stone fireplace and flat screen TV. There is also a separate Exercise Room. The Master Bedroom has a King-size Bed, with luxury linens and the second bedroom holds bunk-beds and a twin futon. The unit is private, w/ a stairway leading directly to the Garage. There is also access to a private washer/dryer, pool, jacuzzi. There is NO Kitchen but a Small frig. and eating area.

Guest favourite

Home in Enfield

4.91 out of 5 average rating, 11 reviews

3 bdrm house great neighborhood

Enjoy plenty of extra room at this spacious home. Fully furnished…Eat in kitchen, relax in the big family room or enjoy alone time in the living room, on-site laundry, WiFi, no cable,free parking. Quiet neighborhood for strolls or enjoy a run around the area. Close to the Massachusetts border as well as minutes from the center of town. Baypathcollege and university within 15 min. Baystate hospital is north about 15 min and Hartford Hospital is south about 30 minutes away

Guest favourite

Apartment in Otis

4.95 out of 5 average rating, 108 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.

Top Guest favourite

Villa in Longmeadow

5 out of 5 average rating, 56 reviews

Comfort and Luxury - 180 year Old Gothic Estate

This 180 year old home provides luxury and comfort for up to 10 guests. Perfect for family gatherings or a group of friends wanting to get away . Chef prepared meals and house keeping services are offered at additional rates. Conveniently located only 15 miles north of Hartford/Springfield BDL Airport and a 5 minute drive to Springfield's MGM casino. PLEASE note that guest of record is required to have at least 3 Five Star reviews in order to book

Guest favourite

Apartment in Holyoke

4.78 out of 5 average rating, 233 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.