House vacation rentals in Hampshire County

Find and book unique houses on Airbnb

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Popular amenities for Hampshire County house rentals

House rentals with a pool

Top guest favorite
Home in Chesterfield
4.98 out of 5 average rating, 55 reviews

High Field Farm

Christopher WRating, 5 stars6 months ago
Set upon the eastern bluffs of the Berkshire hills, Highfields farm is a stunningly beautiful property with great vistas. The autumn leaves were changing and the crisp clear mornings gave way to comfortably warm days.! The night sky was spectacular without light pollution. We will be back
Home in Amherst
5 out of 5 average rating, 8 reviews

Stay in Robert Frost's beautiful house

HilaryRating, 5 stars18 months ago
Lovely home. Everything was as great as we expected. Alexander is a superb host. There was even a great book collection! We look forward to coming back. Thank you Alexander!
Top guest favorite
Home in Westhampton
5 out of 5 average rating, 20 reviews

Happy Valley getaway

BarbaraRating, 5 stars1 week ago
We had a lovely family Easter weekend - 6 adults, 4 kids. The house was very comfortable and spacious. The kids loved the game room and the giant downstairs television! Great yard too.
Guest favorite
Home in Worthington
5 out of 5 average rating, 6 reviews

Morning Side

RebeccaRating, 5 stars4 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 favorite
Home in Northampton
5 out of 5 average rating, 12 reviews

Sun-drenched 6BR Victorian steps from downtown

HerveRating, 5 stars1 month ago
Just What We Needed We had a marvelous trip to Northampton MA and Sue's large Victorian house was perfect for our group's stay. Of course it was clean and comfortable, but in many ways it had more than what we needed, from parking to rooms and other amenities, I was especially pleased to find convenient outlets and USB ports, even by the bed (which is better than some hotels I've stayed at). Sue had a welcoming gift in the kitchen, communicated responsively and helpful with ideas about the area, as our 'home' was truly conveniently located just blocks from the trendy downtown area. An enjoyable stay in a charming city.
Top guest favorite
Home in Amherst
4.97 out of 5 average rating, 39 reviews

Calm Post+Beam Retreat

Daniel PRating, 5 stars6 days ago
Great place just a few minutes away from umass and Amherst. Very peaceful and clean.
Home in Deerfield
4.8 out of 5 average rating, 223 reviews

Perfectly Polished Deerfield Home 5 min to I-91

KimberlyRating, 5 stars2 weeks ago
This place was the perfect fit for my son and myself. Very close to Yankee candle Village minutes from the highway. It was very warming and peaceful. The hosts Ron and Cindy were extremely welcoming and so were the dogs. I would def stay again as I frequent the area.

Weekly house rentals

Top guest favorite
Home in Ashfield
5 out of 5 average rating, 15 reviews

J&J’s Retreat

YixinRating, 5 stars6 months ago
We had a fantastic stay at Joan’s house! She went above and beyond to make us feel welcome, even baking delicious banana bread and providing snacks, wine and water for us. The house was spotless and had everything we needed for a comfortable stay. Highly recommend this place for anyone looking for a cozy and well-kept home away from home. Thank you for a wonderful experience!
Top guest favorite
Home in Northampton
4.94 out of 5 average rating, 70 reviews

Florence Cottage

MelissaRating, 5 stars2 months ago
We booked this adorable cottage for a long weekend honeymoon for our daughter and her military husband. It was so convenient to everything and the space was clean and bright! Anna was extra thoughtful and responsive.
Guest favorite
Home in Becket
4.95 out of 5 average rating, 37 reviews

Pristine Home In Becket Woods

WillRating, 5 stars1 month ago
My dog and I had a wonderful 2 week stay! The house is charming, well appointed and located on a quiet dirt road in a beautiful location. I highly recommend!
Top guest favorite
Home in Goshen
5 out of 5 average rating, 14 reviews

Waterfront Wonderland | Luxe Log Cabin (Sauna/Gym)

AshleighRating, 5 stars2 weeks ago
Wow, I can't recommend Elle's place enough! Beautiful setting and the cabin felt cozy but had more than ample room and privacy for our large party. Everything was spotless and the beds were very comfortable. Elle was a wonderful host and had a huge basket of snacks waiting for us! Checkout was a breeze. We were very appreciative that checkout did not include a list of chores to do! We also loved the sauna. 10 stars!!!
Top guest favorite
Home in Becket
5 out of 5 average rating, 32 reviews

Berkshires Lakefront Stylish Retreat w/Gameroom

LaurenRating, 5 stars3 months ago
We had a lovely long weekend here with family, enjoying the surrounding areas for winter fun. Christina was so responsive and helpful, the space was cozy and the outdoor areas gorgeous!
Guest favorite
Home in Amherst
5 out of 5 average rating, 7 reviews

Amherst Treehouse

DavidRating, 5 stars3 months ago
Victoria's house felt like home. It was so easy to get comfortable and relax and the property is serene and beautiful. It had everything we needed and her communication was clear, helpful and swift. We highly recommend.
Guest favorite
Home in Hadley
4.78 out of 5 average rating, 27 reviews

Amherst/Hadley Country Living 5 Colleges Gardens

ShelleyRating, 5 stars6 months ago
Great home with plenty of amenities. Would recommend to others.
Superhost
Home in Northampton
4.8 out of 5 average rating, 51 reviews

Elegant 2-bedroom apartment in historic downtown

JasmineRating, 5 stars1 week ago
Beautiful home with lots of old house charm. Comfortable beds. Tian was super responsive and clearly communicated everything we needed to know. Walking distance to lots of wonderful shopping and restaurants. Easy check in and check out.

Private house rentals

Top guest favorite
Home in Northampton
4.97 out of 5 average rating, 31 reviews

Spacious and lovely house with hot tub

EveRating, 5 stars6 months ago
Lovely house at on a private cul-de-sac. Lots of room for 3 adult couples in town for a family wedding. Well appointed kitchen. Each couple had a separate bathroom, handy when getting ready for the wedding. Enjoyed hanging out in the comfortable common spaces. Sharing take out in the formal dining room one night was a treat. Beautiful back yard with patio and open porch surrounded by trees.
Guest favorite
Home in Easthampton
4.93 out of 5 average rating, 58 reviews

Sunny Valley Mountain View

LianeRating, 5 stars3 weeks ago
Erin was a great host and very responsive to messages. The place was beautiful, clean, quiet, and I loved the decor. We slept great both nights due to the extremely comfortable beds.
Guest favorite
Home in Ashfield
4.9 out of 5 average rating, 48 reviews

Luxury log style home with views to Mt. Monadnock!

ClaireRating, 5 stars4 months ago
We had a wonderful 5 days at the house and felt right at home. The location is very secluded and peaceful which is exactly what we wanted. It felt very cosy with the woodburning stove. Despite the freezing temperatures we felt very warm and comfortable. We had some communication with Debra beforehand as one of our party had recently broken her arm and conditions at the house were snowy and icy. Debra was very concerned for our safety and was proactive in letting us know the conditions and willing to let us change the date of our booking if we wanted (we didn't), which we very much appreciated. We were met at the property by Jorma who kindly showed us around the house and how to use the woodburner, he also checked in on us a couple of times via text to make sure all was going well. We were provided with lots of info and recommendations about the local area, trails, and things to do. We also had a lovely gift basket on our arrival. Thanks for a lovely vacation!
Superhost
Home in Hadley
4.85 out of 5 average rating, 54 reviews

Farm House of Hadley

DanielRating, 5 stars1 week ago
Staying at Kristen’s farmhouse is a classic Valley experience. The property is located far enough off Route 9 to avoid traffic noise but directly connected for easy access. Do yourself a favor and take the backroads traveling between Hadley and UMASS campus - the correct road back to 116 and 47 is directly accessible. The house is adjacent to a walkable path along a river and right on Hadley common. Very quiet but easy to get out and explore. I would stay at Kristen’s again anytime I’m in the area. It’s perfect for 4-5 people, but note the bottom floor bedroom is noticeably more updated. The second floor bedroom is more of a converted attic space, but plenty of room and perfectly comfortable. The best parts are the shower (water pressure, temperature and space = 👏), the kitchen and how QUIET it is. We know the area and the houses are 100-200 years old. We expected creaky floors and thinner walls. We were astounded at how minimal any noise from inside or outside was. 10/10
Top guest favorite
Home in Northampton
4.98 out of 5 average rating, 61 reviews

Home Away from Home in Northampton

JoannaRating, 5 stars1 week ago
This lovely home is located quite close to town, and is on a very quiet street. We were greeted on arrival by Joan who was quite friendly and showed us around. Joan responded within minutes any time I reached out to her. I had some specific requests when I booked the space, and they were remembered and accommodated, which was so appreciated. The house is well maintained. The beds are quite comfortable and we liked the furnishings. The kid's room is quite sweet and my teen was happy to claim it on arrival. We appreciated how well stocked the kitchen was, and the great book, game and puzzle cabinet. We will return to this house if we come back to Northampton.
Top guest favorite
Home in Ashfield
5 out of 5 average rating, 49 reviews

An 18th century farmhouse

GordonRating, 5 stars2 weeks ago
We had a great time. Actually had heavy snow our first morning that added to the ambiance. Kitchen had everything we needed. We were visiting my daughter at Smith College and enjoyed the contrast between Northampton and the countryside of Ashfield. Looking forward to returning to take advantage of the hiking.
Top guest favorite
Home in Easthampton
5 out of 5 average rating, 16 reviews

An oasis - spacious and bright

JoannaRating, 5 stars6 months ago
Perfect house for traveling with a toddler and family! Beautiful backyard with views of Mt. Tom and lots of books and toys for our kiddo.
Superhost
Home in Chicopee
4.83 out of 5 average rating, 23 reviews

Relax & Enjoy it all to yourself

DavidRating, 5 stars2 weeks ago
Grest house. Would highly recommend to anyone with young kids - playhouse & trampoline and other fun for little ones.

Destinations to explore