Apartment holiday rentals in Cheshire County

Find and book unique apartments on Airbnb

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Popular amenities for Cheshire County apartment rentals

Weekly apartment rentals

Superhost
Flat in Keene
4.82 out of 5 average rating, 202 reviews

The Barry Faulkner Suite: Seasonal Stays

RachelleRating, 5 stars4 months ago
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.
Guest favourite
Flat in Keene
4.98 out of 5 average rating, 60 reviews

"Midtown" at Ro & Oak House

KimikoRating, 5 stars1 week ago
Fantastic place and experience at Hannah’s! Very convenient location and walkable to downtown. Apartment was immaculately clean also and very very spacious. Hannah was quick to respond to questions. If I find myself in Keene again I’ll definitely want to stay here!
Superhost
Flat in Keene
4.5 out of 5 average rating, 8 reviews

Downtown Duplex a Seasonal Stay

MattRating, 5 stars3 months ago
Thank you for being a great host! The house was perfect for our needs.
Guest favourite
Flat in Town of Rockingham
4.95 out of 5 average rating, 275 reviews

Stunning Studio in historic Downtown Bellows Falls

BradleyRating, 5 stars1 month ago
This is one of the favorite places I've stayed at. The unit had character and the building did as well. Great high ceilings, spacious and well decorated. The village is lovely and walkable. Remy was pleasant and is involved with one of the restaurants downstairs, which is a must for a meal while you are in town. Can't speak highly enough of the experience.
Superhost
Flat in Keene
4.79 out of 5 average rating, 56 reviews

Abbott Handerson Thayer Suite: Seasonal Stays

MarkRating, 5 stars3 weeks ago
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!
Guest favourite
Flat in Keene
4.94 out of 5 average rating, 220 reviews

The Carriage House Loft: Seasonal Stays

StephenRating, 5 stars1 month ago
Fantastic location and a really comfortable place to stay with a great feeling of space inside
Guest favourite
Flat in Keene
5 out of 5 average rating, 21 reviews

The Darling Suite

GarnerRating, 5 stars3 days ago
The space was newly renovated. There was intricate trim molding around the doors. The grey hardwood floors gave a a contemporary vibe mixed with the historic see through floor in the kitchen. The patio in the back was spacious and had a gas grill. The area was quiet at night and we felt very safe. The property is well cared for and we would definitely go there again. We enjoyed the short ride to the downtown area. The bike riding trails were in close proximity. Garner and Marylu give it a thumbs up!
Superhost
Flat in Keene
4.83 out of 5 average rating, 59 reviews

Murray's Gallery: Seasonal Stays

ChristinaRating, 5 stars4 months ago
Great place to stay close to downtown! Very walkable. Even more spacious in person than the pictures made it look!

Private apartment rentals

Guest favourite
Flat in Harrisville
4.94 out of 5 average rating, 31 reviews

The Nest at Aldworth Manor

DonRating, 5 stars1 month ago
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....
Top guest favourite
Flat in Town of Rockingham
4.91 out of 5 average rating, 79 reviews

Lovely light-filled 2 bedroom flat

BrendaRating, 5 stars3 days ago
Sweet place. Comfortable, Quiet and safe. Three things I look for!
Guest favourite
Flat in Keene
5 out of 5 average rating, 5 reviews

Dover by Downtown

RyanRating, 5 stars2 weeks ago
Nice place. Very clean. Well-stocked. Short walk to downtown Keene with lots of restaurants and breweries. Great communication! Owner even put in a fire pit after I asked if she had one!
Guest favourite
Flat in Putney
4.97 out of 5 average rating, 97 reviews

Minimal 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 favourite
Flat in Keene
5 out of 5 average rating, 6 reviews

Cozy unit in Downtown Keene

LisaRating, 5 stars1 week ago
Wonderful stay and convenient to everything!
Guest favourite
Flat in Jaffrey
4.97 out of 5 average rating, 33 reviews

Schoolhouse No. 1

JenniferRating, 5 stars1 month ago
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!
Superhost
Flat in Peterborough
5 out of 5 average rating, 3 reviews

"Always Summer" Walk to Downtown

RobertRating, 5 stars9 months ago
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.
Superhost
Flat in Putney
4.93 out of 5 average rating, 81 reviews

Southern Vermont Getaway

StephenRating, 5 stars3 months ago
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.

Family-friendly apartment rentals

Flat in Winchester
4.68 out of 5 average rating, 44 reviews

Beautiful lake side getaway, quiet.

BrittRating, 5 stars2 months ago
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.
Private room in Harrisville
4.83 out of 5 average rating, 158 reviews

Apartment by the Lake

JenRating, 5 stars1 month ago
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!
Top guest favourite
Flat in Jaffrey
4.95 out of 5 average rating, 75 reviews

Apartment in Historic Home

LaurieRating, 5 stars6 months ago
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.
Guest favourite
Flat in North Westminster
4.9 out of 5 average rating, 68 reviews

Private 1st Floor Apartment/ Secluded Paradise

JamesRating, 5 stars7 months ago
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