House holiday rentals in Cheshire County

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for house rentals in Cheshire County

House rentals with a pool

Superhost
Home in Winchendon
4.75 out of 5 average rating, 4 reviews

The Perfect Spot at the Lake @ Tatum's Place

AshleyRating, 5 stars3 months ago
Great stay! House was clean and spacious for our party of 8. We had everything we needed for our weekend stay in January. We traveled with our twin 18 month olds and had access to playpens and a high chair for which I was very grateful! They even had some books and legos for the kids to play with!
Superhost
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars6 months ago
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!
Superhost
Home in Winchendon
4.95 out of 5 average rating, 22 reviews

Amazing Lakefront Home with Pool- Tatum's Place

NidhiRating, 5 stars2 weeks ago
Great stay overall — just be mindful of seasonal comfort! We had a lovely time at this beautiful property — it’s well-maintained, peaceful, and has a lot of charm. The host was responsive and check-in was easy. Just a heads-up for future guests: the property has seasonal settings, so you’ll either get heat or A/C depending on the time of year, not both. It made things a bit uncomfortable during a weather transition, but manageable. Still, the beauty and uniqueness of the space definitely made up for it. Would recommend with that one caveat in mind!

Weekly house rentals

Top guest favourite
Home in Antrim
4.97 out of 5 average rating, 79 reviews

The Cozy Place

LauraRating, 5 stars4 months ago
We had such a great time here even in the winter! Pats peak is 20 minutes away so we did some skiing and had a nice clean, warm home to come back to! Thanks Laura and Hanna!
Guest favourite
Home in Northfield
5 out of 5 average rating, 8 reviews

Minimalist forest retreat

JoseRating, 5 stars7 months ago
We had a great stay at Sally and Noava’s place! The surroundings were so peaceful and beautiful, truthfully a cabin in the woods. The house was perfectly clean and relaxing. The hosts were so responsive making it that much more comfortable of a stay. We would definitely come back here again!
Guest favourite
Home in Brattleboro
4.79 out of 5 average rating, 24 reviews

Eco Friendly Garden House

JayRating, 5 stars3 weeks ago
When we walked into the house my wife and I both felt at home. Loved the earthy feel (wood stove, cast iron cookware).
Top guest favourite
Home in Rindge
5 out of 5 average rating, 83 reviews

The Crowcroft House

JoyRating, 5 stars4 months ago
Family of four stayed for a week while visiting family. As I think one other review may have said, the description is accurate however the space is much more roomy than the photos would have you believe. Two full bathrooms, a washer and dryer, incredible kitchen, comfortable beds and a serene location all made this location an incredible space but the small, thoughtful touches like hair towels, cotton rounds/swabs/balls in the main bath made our stay exceptional.
Superhost
Home in Rindge
4.93 out of 5 average rating, 73 reviews

Charming Lake Front Home

DawnRating, 5 stars8 months ago
A great spot for R & R! We loved being right in the lake, great view, private and quiet, hiking, walking trails, kayaking! Plenty of room to spread out! Clean and all amenities supplied! We enjoyed family and friends through the week. Local to Mt Madanock.
Guest favourite
Home in Rindge
5 out of 5 average rating, 21 reviews

Changes in Attitude

KatherineRating, 5 stars6 months ago
We had a wonderful fall trip and stay at Lorraine's well-appointed cabin. It is very tastefully designed with everything you need. We love cooking and she had everything we needed, including oil & some spices. We climbed Mount Monadnock on one of the most beautiful fall days and were able to take the kayaks provided out on Contoocook Lake one morning and it was so beautiful. The bed was comfortable, the heat worked great, the shower was hot and we loved all the cozy touches. The bottle of champagne was unexpected, but so appreciated. We didn't spend too much time on the porch or use the fire pit because we were out & about enjoying, but those were other great benefits! The trail behind the house to the water in gorgeous in fall. Highly recommend this Airbnb!
Superhost
Home in Troy
4.78 out of 5 average rating, 41 reviews

Monadnock 4-Bedroom Charmer by Cheshire Rail Trail

DzmitryRating, 5 stars3 months ago
Best stay in this area, thanks
Top guest favourite
Home in Stoddard
5 out of 5 average rating, 11 reviews

Water views, 2 min to public beach, 4 bedrooms

Yolanda SRating, 5 stars4 days ago
I had an excellent experience staying at Jennifer’s place! The home was exactly as described—clean, comfortable, and well-stocked with everything I needed. The location was perfect for enjoying a quiet weekend. Jennifer was a wonderful host very attentive and respectful.

Private house rentals

Top guest favourite
Home in Nelson
5 out of 5 average rating, 11 reviews

The Boat House on Granite Lake

MichelleRating, 5 stars1 week ago
We stayed at the boathouse while in the area for a family wedding. We were very happy with how clean, cozy and beautiful this place was! Jennifer was very responsive and accommodating. This home had everything you could need for a relaxing stay. The games came in perfect during a rainy day, and the views of loons and a beaver on the lake was a treat.
Top guest favourite
Home in Walpole
5 out of 5 average rating, 70 reviews

Walpole NH Peaceful Farmhouse Getaway-VT/NH Border

LoribethRating, 5 stars7 months ago
Stunning property with beautiful views and tons of charm. Very warm and friendly quintessential New England farmhouse.
Guest favourite
Home in Walpole
4.89 out of 5 average rating, 19 reviews

Country Cottage

SiruiRating, 5 stars2 months ago
Great place! We went to ski and chose this house for one night. It was great
Superhost
Home in Fitzwilliam
4.84 out of 5 average rating, 77 reviews

Covey House Retreat with Sauna/Red Light/Biomat

BernardRating, 5 stars4 days ago
This place was great and perfect for my circumstances. My ex-boyfriend passed away, and this place was awesome to be in. It was very calming, spacious, and beautiful. Having been there in person, the pictures do not do it justice! Last but not least, I also tried out some of her services for healing,. I will definitely be coming back!!
Superhost
Home in Town of Rockingham
4.86 out of 5 average rating, 76 reviews

Beautiful Victorian Home

RyenRating, 5 stars5 months ago
Barbara, was an amazing host. Her house is absolutley beautiful. Amazing kitchen, that is perfect, for so many occasions. Very kid frinedly, our family loved staying here, would highly reccomend. Quick to reapond and gives tips and reminders or important information as to where things are 😊
Home in Putney
4.83 out of 5 average rating, 6 reviews

Charming 4-bedroom house

MaryRating, 5 stars2 months ago
Jeremy's house was the perfect spot for a winter get away! The house is thoughtfully designed and furnished and decorated in a way that feels both elegant and comfortable. The space was perfect for our 3 generation family of 8, with room for the littles to play while parents and grandparents cooked in the well-equipped kitchen, and enjoyed each others' company with the warmth from the wood stove while watching the snow fall on the hills and fields outside. We felt truly "at home". The beds are super comfortable, with organic cotton bedding and cozy down comforters. We slept well after sledding and snowshoeing in the yard and cross country skiing on the amazing trails at the Putney School, just a 10 minute drive away. Jeremy was incredibly responsive and accommodating, and followed up to make sure we had everything we needed for a great stay. Our only regret is that the deep snow cover meant we didn't get to enjoy the patio and fire pit - we will have to come back in the warmer weather!

Destinations to explore