Holiday 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 favourite

Bungalow in Easthampton

4.92 out of 5 average rating, 504 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

Flat in Northampton

4.9 out of 5 average rating, 193 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.

Campervan/Motorhome in Village of Pelham

5 out of 5 average rating, 3 reviews

Upscale RV - 1 king BR w/Pool! Near Amherst

Spacious 35-ft camper w/private king BR for 1-2 guests, plus 2 twin sized "sleeping pads" if needed for kids. Full kitchen & outdoor grill. Heat & AC. Shower & toilet. Chromecast TV & Bluetooth sound system. Private pool (Jul & Aug only) & firebowl. Free parking for 1 vehicle. Only 8 mins to Amherst & 25 mins to Northampton. Plenty of wildlife & lots of excellent trails (Buffam Falls, Quabbin Reservoir, Lake Wyola, etc). Top-notch stargazing on clear nights. Come get away to the country...

Home in Deerfield

4.81 out of 5 average rating, 227 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!

Cabin in Sunderland

New place to stay

3 Mi to UMass Amherst: Peaceful New England Cabin

Pet Friendly w/ Fee | Private Pool | Secluded Setting | Orchards Nearby No matter what brings you to town, you'll feel right at home at this spacious vacation rental in Sunderland, MA! Located on a tranquil yet convenient private property, this 3-bedroom, 2-bathroom cabin allows you to kick back and relax while never being too far from what's important. When you're done exploring the lush forests of New England or strolling through Amherst, return to a crackling fire and a gooey s'more.

Top guest favourite

Guest house in Northampton

5 out of 5 average rating, 5 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 Amherst

5 out of 5 average rating, 9 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 favourite

Guest suite in Amherst

4.96 out of 5 average rating, 298 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 favourite

Home in Worthington

5 out of 5 average rating, 7 reviews

Morning Side

Morning Side is a charming New England colonial home located in the center of Worthington. The house is set back and landscaped, offering privacy with a fenced in backyard that has a heated, in-ground pool, goshen stone patio, outdoor dining and barbecue area and several acres of open yard that is landscaped with a variety of trees and stone walls to meander and enjoy your time in the country.

Guest favourite

Home in South Hadley

5 out of 5 average rating, 6 reviews

Dog friendly, 2 fireplaces,Pool, Pickleball, 3 bd

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. 2 working fireplaces and 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.

Guest favourite

Flat in Holyoke

4.78 out of 5 average rating, 223 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.