House holiday rentals in Hampshire County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Hampshire County

House rentals with a pool

Top guest favourite
Home in Chesterfield
4.98 out of 5 average rating, 58 reviews

High Field Farm

CatherineRating, 5 stars1 week ago
Such a relaxing place, space for everyone to spread out and to gather…kids played in the barn because it was a rainy weekend and sadly too cold for a swim. Great kitchen with all necessities. four minutes to gorge trail head where my son ran 50 miles in the beast coast ultra. highly recommend
Home in Amherst
5 out of 5 average rating, 8 reviews

Stay in Robert Frost's beautiful house

HilaryRating, 5 stars20 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 favourite
Home in Westhampton
5 out of 5 average rating, 26 reviews

Happy Valley getaway

DamarisRating, 5 stars3 days ago
We enjoyed our stay! Everything was beautiful and our Hosts were great and very responsive. We would definitely recommend and hopefully get to come back 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 stars2 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, 226 reviews

Perfectly Polished Deerfield Home 5 min to I-91

WillRating, 5 stars2 weeks ago
good space for a medium sized group or family. hosta are very nice. beautiful surroundings.
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

Weekly house rentals

Superhost
Home in Easthampton
4.67 out of 5 average rating, 3 reviews

2BR Private Home~Old World Charm

KathyRating, 5 stars1 week ago
Mindy & her spacious home were perfect; just what we needed for a last-minute trip to Easthampton. The location on beautiful acreage is centrally located… Just minutes from the quaint uptown & many shops and groceries. Everything was immaculately clean & we especially appreciated the detailed information she left throughout the house so that we could understand what light switches did what, how to use the washing machine, the preference for having an outdoor light on at night, etc. Mindy thought of everything. She greeted us upon arrival, had pleasant conversations when we’d see her out & about on the property, & was prompt/helpful when we had questions. Bed/pillows were very comfortable, seating in living room was relaxing & comfortable, kitchen was fully stocked & perfect for cooking all our meals. Shower & bathroom were modern, with ample hot water. Washer & dryer were so convenient. We rented downstairs but were allowed to look up…we will definitely rent entire house for family!
Guest favourite
Home in Easthampton
4.92 out of 5 average rating, 61 reviews

Sunny Valley Mountain View

ChrisRating, 5 stars4 weeks ago
We were visiting our son and new grandchild in Easthampton for a week and Erin's apt was ideal in terms of location and a peaceful environment. The neighborhood is beautiful and quiet. Her open air second floor porch was a gem. The kitchen was very well-appointed. The apt was more spacious than we expected and had wonderful extra rooms and furnishings. It is also very competitive price wise for the Pioneer valley. Erin is very kind and responsive. We will certainly consider another stay when we are in Easthampton.
Guest favourite
Home in Becket
4.92 out of 5 average rating, 26 reviews

Forest Home with Sauna

MissyRating, 5 stars5 months ago
Our second stay and would return again. Beautiful and well maintained home in a picturesque setting in the always beautiful Berkshires. Pele is a responsive and helpful host, while amenities in her home ensure a comfortable stay.
Guest favourite
Home in Sunderland
5 out of 5 average rating, 16 reviews

Charming and Cozy Hilltop Home

KimberlyRating, 5 stars3 months ago
The words that come to mind is this place is breathtaking. The host was amazing and sends awesome videos of the wildlife at night. There isn't enough to say about how at home you feel here. Would love to stay again if I'm in the area. Thank you Barbara and Max
Top guest favourite
Home in Northampton
4.98 out of 5 average rating, 44 reviews

Low-scent, historic, well-located downtown house

LuisRating, 5 stars1 week ago
Plenty of space to spread out and a nice yard if the weather allows you to enjoy it. Easy walk if you are hungry or just want to check out the town. Debra is kind and accommodating. She is enthusiastic about her home and the beautiful area she resides in. Already planning a trip back to enjoy more of the biking and hiking in this area.
Guest favourite
Home in Becket
4.95 out of 5 average rating, 37 reviews

Pristine Home In Becket Woods

WillRating, 5 stars3 months 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!
Superhost
Home in Chicopee
4.78 out of 5 average rating, 27 reviews

Relax & Enjoy it all to yourself

AlexRating, 5 stars2 weeks ago
We had a great stay at the hiuse. It was clean comfortable and had everything we needed. No hesitation to book again next time. Thanks Natalya
Top guest favourite
Home in Becket
5 out of 5 average rating, 33 reviews

Berkshires Lakefront Stylish Retreat w/Gameroom

BenRating, 5 stars2 weeks ago
What an amazing stay. The house is right on a peaceful pond and our kids had the best time exploring every day by canoe. We saw foxes, beavers, tons of birds, and ended each day with s’mores by the fire. Total magic! The house itself was super comfortable and had everything we needed. And the full-size arcade machines were a huge hit with the kids! We’d come back in a heartbeat!

Private house rentals

Guest favourite
Home in Northampton
4.98 out of 5 average rating, 63 reviews

Home Away from Home in Northampton

LynnRating, 5 stars3 weeks ago
House is beautiful w carefully selected furnishings & art! The owner goes above & beyond w food items & a wide array of toiletries/extras. Separate heat/air control in each bedroom. Beds were comfortable, high quality bedding. Bedrooms have ample storage/seating. Well equipped for kids - toys, books, games, art supplies, high chair, first aid, etc. Keep in mind the 1 bathroom is upstairs. We loved the charming kitchen - mix of old/new components, beautiful selection of dishware, large sliding window. Appliances + toaster, microwave, electric kettle, 2 coffee-making options, selection of tea/coffee, pantry staples, cleaning supplies. Directions posted for trash, recycling, compost. Rules seemed overwhelming at first but turned out to be helpful. Front porch great for relaxing - overlooks the street, pretty sidewalk flower garden, charming neighborhood. Street parking fluctuated but always found a spot. Location is walkable to restaurants, coffee shops, shopping, concerts, Smith College!
Guest favourite
Home in Williamsburg
4.85 out of 5 average rating, 41 reviews

Cute and Cozy Lake Cottage

BarbaraRating, 5 stars4 weeks ago
While the weather was not optimal (sometimes western MA spring is slow to come), we loved the cottage. It is perfect for walking, hiking, reading and other quiet activities. But, you have access easily to Northampton or other local towns for a meal or night out. Debra was easy to reach but not at all intrusive. Check in was smooth. All in all, a lovely experience.
Guest favourite
Home in Otis
4.93 out of 5 average rating, 15 reviews

Spacious Lake Front Home

JeanRating, 5 stars6 months ago
Beautiful location in Otis, right on the lake and so peaceful. The house is very spacious and easily accommodated our family ( 7 adults and 2 children). All the windows in the house provided great views of the lake, especially from the deck. Our host Nick was very responsive when we had questions or any concerns. Would be nice to come for a stay during the summer.
Top guest favourite
Home in Easthampton
5 out of 5 average rating, 16 reviews

An oasis - spacious and bright

JoannaRating, 5 stars7 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.
Guest favourite
Home in Becket
5 out of 5 average rating, 14 reviews

Private Lakehouse in the heart of the Berkshires

AaronRating, 5 stars7 months ago
I want to say thank you to Christopher and his family for allowing my friends and me to stay in their home. it was clean, beautiful, serene and exactly what it was described to be. Christopher, your suggestions on golf courses for my friends and me were exceptional. I hope we were as good of guests as you were hosts!
Guest favourite
Home in Becket
4.94 out of 5 average rating, 31 reviews

Lakefront Cottage on Private Beach

GillianRating, 5 stars2 weeks ago
Our family had an AMAZING stay in this cottage. It was clean and comfortable, and just what we were looking for. A quiet spot where we could enjoy fishing, kayaking, biking, etc with the comforts of home. Because of all the amenities offered, we didn’t have to pack too much which is always a bonus! We are already talking about our next visit 😊
Guest favourite
Home in Becket
4.92 out of 5 average rating, 25 reviews

Lakefront Jewel By: Evergreen Home

ItayRating, 5 stars1 month ago
The house was great and had most of what we needed, we used it as a base for a motorcycle trip.
Guest favourite
Home in Easthampton
4.9 out of 5 average rating, 61 reviews

Charming 4 bd/2 bth home near Williston

SonyaRating, 5 stars3 weeks ago
We stayed here for graduation weekend from Smith College. It was an easy drive and nice to be a little removed. The house was perfect for a large group and the host was very responsive! We loved the neighborhood and the back deck. It was also fun for the kids in the group to watch the high school track meet one afternoon. The layout worked very well and the beds were very confortable. Probably one of my favorite air bnbs.

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