Vacation 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 favorite

Bungalow in Easthampton

4.92 out of 5 average rating, 476 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

Campsite in Brimfield

5 out of 5 average rating, 8 reviews

Cozy Campground Cabin #2 Steps From 420 Acre Lake

Ammenities include a pool, beach access, bath houses,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, toaster 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.

Guest favorite

Rental unit in Northampton

4.98 out of 5 average rating, 288 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 Enfield

4.91 out of 5 average rating, 11 reviews

3 bdrm house great neighborhood

Get comfortable and 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.

Superhost

Rental unit in Northampton

4.88 out of 5 average rating, 164 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.

Guest favorite

Rental unit in Northampton

4.98 out of 5 average rating, 192 reviews

Skylights, art + design in best downtown location

Elegant spacious sun-drenched 2-bdrm penthouse in gracious 4-family Victorian on tree-lined street in the heart of downtown Northampton. Easy walk to Smith College campus. Skylights; large tiled bathroom with shower, jacuzzi tub, washer/dryer; hardwood floors; renovated kitchen with Italian-tiled floor; open floor plan with ample dining area; living area with large leather couch, handmade rustic wood coffee table, 42" TV, Yamaha digital piano, cathedral ceiling, and glass doors onto a balcony.

Guesthouse in Northampton

5 out of 5 average rating, 3 reviews

Newly Constructed Guest House with Pool

New (2023) 200 sf guest house adjacent to our home. Space complete with wifi, heat, A/C + ceiling fan. Includes full size sleeper sofa (Room + Board, no springs!), sleeping loft, kitchenette w/sink and mini fridge, half bath, outdoor shower, private patio and in-ground pool. Dedicated outdoor lighting allows for nighttime enjoyment of guest house, pool and enclosed yard. Walking distance to Florence center, 2 miles from downtown Northampton. We have a friendly dog who suns herself in our yard.

Guest favorite

Home in Brimfield

4.87 out of 5 average rating, 71 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 favorite

Home in Blandford

5 out of 5 average rating, 5 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.

Guest favorite

Rental unit in Northampton

4.99 out of 5 average rating, 106 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

Villa in Longmeadow

5 out of 5 average rating, 51 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 favorite

Home in South Hadley

5 out of 5 average rating, 5 reviews

Pool, Pickleball, 3 bed/2 bath

Lovingly renovated mid century modern home very close to Mt Holyoke College with a pool and gourmet kitchen. Hardwood floors throughout and the most comfortable beds and amenities. Tennis court with pickleball set up and basketball hoop all on 1.8 acres. I live in a connected in law apt with my delightful hypoallergenic dog with totally separate entrance.