
Apartment vacation rentals in Cheshire County
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Top-rated apartment rentals in Cheshire County
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Popular amenities for Cheshire County apartment rentals
Weekly apartment rentals

The Barry Faulkner Suite: Seasonal Stays
This was a spacious, comfortable, clean apartment full of old New England charm. You feel like Ralph Waldo Emerson or Margaret Fuller are going to come up the stairs for some tea and conversation. Every room felt inviting to hang out in and the apartment had everything you need for a family to get away for a few days. The pictures on the walls were endlessly fascinating. The beds were very comfortable and the bedrooms spacious and cozy at the same time. The house is basically a block off the main square in downtown Keene and walkable to the Keene Public Library (among other things) so the location was perfect. We were there over a frigid few days in January and the heat was on and kept us toasty the whole time. My only suggestion would be a few more bowls/serving items in the kitchen. Would love to stay here again.

Gorgeous 1-Bedroom Space in Historic Bellows Falls
Remy was a great host! Perfect place to stay in Bellows Falls! Easy parking and great restaurant right below! Highly recommend staying here!

"Midtown" at Ro & Oak House
This was a beautiful apartment conveniently located to downtown. The kitchen and rooms were updated to feel modern and welcoming though it had details reflecting its historic past. The shower had the best water pressure I’ve experienced in a long time. Hannah was very communicative and I would definitely stay here again.

"The Ramsdell Suite @ The Large House"
Another enjoyable & super excellent stay at Shane's place! Very comfortable & safe, impeccably clean first floor apartment. Shane is an extremely kind, attentive, super excellent Host!

Downtown Duplex a Seasonal Stay
Thank you for being a great host! The house was perfect for our needs.

Abbott Handerson Thayer Suite: Seasonal Stays
This place was a great place to walk to downtown and to bike around the area! We enjoyed our 6 days in Keene and this place being so close, was great! Everything was comfortable and we enjoyed the place! There is some minor noise at night, but is manageable. Super place and would go back to stay if in the area again!

Spacious Studio in VT Village
Spacious room in the heart of a classic Vermont village.

Murray's Gallery: Seasonal Stays
Great place to stay close to downtown! Very walkable. Even more spacious in person than the pictures made it look!
Private apartment rentals

The Nest at Aldworth Manor
We were attending a wedding at a nearby venue, and this place worked out great! I hope to come back one day when I am doing the Sunapee to Monadnock Greenway Trail....

Lovely light-filled 2 bedroom flat
We really enjoyed our stay at Kristen’s place in Rockingham. Location was perfect, very quiet at night and very easy to walk into the little town of Bellows Falls. The bed was comfortable and the apartment was very spacious. We would highly recommend and definitely return.

Minimal organic hideaway inspired by nature
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.

Schoolhouse No. 1
Such a gorgeous little place! We stayed because we were in between places at the time, stayed 16 days total. David responded quickly to questions or issues that we had. Only thing I would have liked to see was another lock of sorts on the door, my 2 year old knows how to use door handles(he hasn’t figured out door knobs yet) and tried to escape a few times so another lock that he couldn’t reach would have been great. Otherwise, amazing stay!

"Always Summer" Walk to Downtown
The only negative for us was the television/Roku. We were unable to figure out how to watch some live news shows and various other programs that we know were televised. A written primer or directions on how to use Roku effectively would have. been nice. I did not bring this to Lindsay's attention as I should have.

Privacy, View, Amenities, Gym, Garage included too
Laura’s place was better than expected. The pictures don’t do it justice. I wish I knew about it 4 years ago when my son started college. I would’ve stayed there every year. They are very welcoming. The suite is amazing and the scenery is beautiful. I wish we could’ve stayed there longer.

Southern Vermont Getaway
Really nice spot in the country - a great value. The double bed is in a loft. There is a settee where someone can sleep on the first floor.

Mountain View Getaway
Wonderful spot to stay for a weekend ski trip. Super helpful hosts. Would definitely book again.
Family-friendly apartment rentals

Beautiful lake side getaway, quiet.
Very nice place. The lake is gorgeous. Wish it was warmer, so i could use the kayaks. Bill and Sandie are very friendly and helpful. Their not intrusive at all, but were very responsive to any questions or concerns we had. I would definitely stay here again.

Apartment by the Lake
We are returning guests and we’re thrilled to see the property and surrounding area in spring. We were serenaded by nearby loon calls and found our whole stay quite peaceful. This is a special place at a great price!

Apartment in Historic Home
Jeanne's place was perfect, and I will definitely be staying again. Location was 5 miles from my family, and I had a wonderful time. Jeanne was very responsive and easy to communicate with.

Private 1st Floor Apartment/ Secluded Paradise
My stay at paradise Island was great and exactly what I needed for a couple weeks while I was working on a project ,I was able to relax ,rest, and enjoy a nice peaceful area and set my mind at ease ,met such wonderful hosts and very welcoming ,I appreciate the hospitality and what a beautiful place thank you again .
Destinations to explore
- Rentals with a kayak Cheshire County
- Rentals with a hot tub Cheshire County
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- Rentals with lake access Cheshire County
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- Kid-friendly rentals Cheshire County
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- Rentals with a fireplace Cheshire County
- Rentals with a patio Cheshire County
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Bear Brook State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Manchester Country Club - NH
- Berkshire East Mountain Resort
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Ragged Mountain Resort
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Nashoba Valley Ski Are
- Clarksburg State Park
- Mount Tom State Reservation
- Brattleboro Ski Hill
- Bretwood Golf Course