
Vacation rentals in Cheshire County
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Top-rated vacation rentals in Cheshire County
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Top guest favorite

Home in Jaffrey
4.97 out of 5 average rating, 76 reviewsWillow Falls Home ~Hot tub & Waterfront
JoyRating, 5 stars1 week ago
Such an amazing place to stay - easy to get to surrounding towns and local attractions but the physical location and the space lends itself to such a beautiful tranquility and peace we could feel ourselves relaxing the minute we got out of the car. Everything we could have wanted was provided, including a washer and dryer, the beds were so very comfortable, and being able to soak in the hot tub beneath the stars after a long day was just an added bonus. We were so grateful to be able to be in this space for about a week and hope to be able to rerun in the future!
Top guest favorite

Home in Swanzey
5 out of 5 average rating, 6 reviewsLake Front Cottage
JordanRating, 5 stars8 months ago
My wife and I escaped to Swanzey for our one year anniversary. When we arrived, Kate knew we were showing up late, so she left lights on and a little dessert + bottle of wine for our celebration. Kate was very responsive, left recommendations for where to go and made this an excellent stay.
Guest favorite

Apartment in Putney
4.97 out of 5 average rating, 97 reviewsMinimal organic hideaway inspired by nature
ItaRating, 5 stars3 weeks ago
Katherine’s space was so cozy! It was exactly what I needed for a retreat from daily life. I found both the loft and the daybed very comfortable. There were dimmers on most of the light fixtures, which was important to me because I like low-light settings. The kitchen included a counter with stools and was really quite beautiful. This Airbnb was within walking distance to a local restaurant, the general store and a food co-op. I decided not to rent a car because I was there for R&R., however , if you had a car, just a few minutes outside of town you would see beautiful trees all with leaves in there spring splendor. You could get to Brattleboro in about 20 minutes if you’re looking for more choices of restaurants.. (I decided to take the train up so I took a taxi to the Airbnb from the train and back to the train at the end of my trip.). Although it rained most of the time I was there, it was perfect for my goal of R&R.
Guest favorite

Apartment in Keene
5 out of 5 average rating, 6 reviewsCozy unit in Downtown Keene
NellRating, 5 stars1 week ago
Great location! Newly renovated and extremely clean space! Very happy with the comfort of the apt. Traveled to Keene for work - perfect place for rest and meals. Would stay again in the same scenario. Zack was very responsive and helpful. Thank you for the treats and perfectly stocked kitchen.
Guest favorite

Cottage in Brattleboro
4.97 out of 5 average rating, 31 reviewsOn the Water at North Bridge Cove
StephRating, 5 stars3 weeks ago
2nd time staying here, lovely little spot on the river. Well-priced and met our needs. Best for 1-2 travelers and folks who either have a car or don't mind the easy walk into town. I'll likely stay here again when I next visit Bratt!
Guest favorite

Cottage in Keene
4.84 out of 5 average rating, 70 reviewsHeron Cove Cottage: A Sweetwater Stay
SamuelRating, 5 stars2 weeks ago
Celia’s cottage was the perfect setting for a father daughter weekend. We comfortably enjoyed some fishing off the dock (perfect for a kindergartener), curling up On the couch and watching a movie on a rainy evening and being close to everything Keene has to offer. Thank you for hosting a great weekend for us!
Top guest favorite

Farm stay in Jaffrey
5 out of 5 average rating, 54 reviewsComfy Quarters Suite 2 Saltbox Hideaway
JoeRating, 5 stars2 days ago
Lori was super attentive and accommodating - clear communication and direction. The place is cool! Loved the room - so warm and at home feel. The view from the porch is sweet. And there is even a stone motorcycle to boot! I am certainly going back!
Guest favorite

Treehouse in Alstead
5 out of 5 average rating, 21 reviewsOwls Nest Treehouse
NicoleRating, 5 stars1 month ago
Super cozy and really innovative tree house. The bathroom especially with the rain shower head was amazing. Mirror was interesting also with special lighting. Decor is perfect for the setting in the cedar trees. Rustic and dreamy. ⭐️
Destinations to explore
- Apartment rentals Cheshire County
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- Waterfront rentals Cheshire County
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