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Holiday rentals with a pool in Hampshire County

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Popular amenities for Hampshire County rentals with a pool

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Top Guest favourite
Home in Chesterfield
4.98 out of 5 average rating, 59 reviews

High Field Farm

TracyRating, 5 stars3 days ago
⸻ A perfect countryside escape! This was our second stay at High Field Farm, and it was just as amazing as the first. The farmhouse is beautiful, with spectacular woodland views from every window that make it feel like a peaceful retreat. It’s incredibly relaxing and well-stocked with all the essentials you could need. Everything was spotless and exactly as described. Jenny is a wonderful host—warm, responsive, and thoughtful. We’re already looking forward to our next visit. Highly recommend to anyone looking for a tranquil getaway in nature!
Home in Amherst
5 out of 5 average rating, 9 reviews

Stay in Robert Frost's beautiful house

PattyRating, 5 stars2 weeks ago
Wonderful historic home that is very comfortable and extremely well located. We would definitely love to stay here again the next time we come to Amherst - whether that’s with kids or with other couples.
Top Guest favourite
Home in Westhampton
5 out of 5 average rating, 27 reviews

Happy Valley getaway

ChrisRating, 5 stars5 days ago
We had a wonderful stay in Westhampton. The place itself had plenty to do and was well stocked with amenities. The owners were also very proactive in letting us know about an issue with the previous renters that resulted in a deeper cleaning than expected. Nevertheless, we recommend Jen’s house and would definitely stay there again.
Guest favourite
Home in Worthington
5 out of 5 average rating, 7 reviews

Morning Side

RebeccaRating, 5 stars6 months ago
Morning Side is filled with character and charm. The house itself, the furnishings, and even the book collection take you back to 18th century New England. The kitchen and dining area are particularly cozy and inviting. The windows and views are magical, particularly with a good snowfall. The host was very helpful, particularly proactive about preparing the sidewalk and driveway for snowfall, even on Thanksgiving Day!
Guest favourite
Home in Northampton
5 out of 5 average rating, 14 reviews

Sun-drenched 6BR Victorian steps from downtown

KevinRating, 5 stars3 weeks ago
I wish I had known about this property sooner for my visits to Amherst College. It was better than advertised. Sunny, clean, comfortable and so close to walk to town. My whole family enjoyed it very much.
Home in Deerfield
4.81 out of 5 average rating, 227 reviews

Perfectly Polished Deerfield Home 5 min to I-91

LisaRating, 5 stars2 weeks ago
A great place to stay and very quiet! Loved having basic amenities like tea and coffee, cereal, orange juice, butter, and spices available. A nice touch!
Guest favourite
Home in South Hadley
5 out of 5 average rating, 6 reviews

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

BrianRating, 5 stars8 months ago
This was exactly what we needed for a trip out to see our son at school. Not only did it have what we needed but so much we didn't know we wanted. An excellent kitchen, plenty of space, dog friendly, a pool and pickleball! We had a couple of big battles with the kids while they were at the house for some much needed home cooking. The bed was very comfortable and Mary was very helpful if needed. I look forward to many future stays at Mary's home
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