House vacation rentals in Cheshire County

Find and book unique houses on Airbnb

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Popular amenities for Cheshire County house rentals

House rentals with a pool

Home in Troy
4.59 out of 5 average rating, 22 reviews

Mountain View escape

HelenRating, 5 stars3 weeks ago
We had a wonderful stay at Jon‘s place. The surroundings are very peaceful and we loved spending time in the hot tub and enjoy the view. The living room is huge and the entertainment options were great for the weekend. Jon was very responsive and helped us with our questions. Two things I noticed: The layout of the house is a little interesting with three out of four bedrooms connected, but it worked for us. And the upstairs bedrooms don’t have blinds or curtains, so it was bright quite early. But I would stay here again and enjoy a peaceful, relaxing weekend.
Superhost
Home in Winchendon
4.95 out of 5 average rating, 20 reviews

Amazing Lakefront Home with Pool- Tatum's Place

AnnRating, 5 stars1 month ago
What a perfect places for family and friends long weekend ski trip. Our group consisted of 8 adults and 8 children (ranging ages 4-11). quick drive for tubing and ski/snowboarding. one of the bedrooms was a tricky location since you had to walk through it to get to the lower level kitchen/living room and another bedroom. overall would love to come back again if planning a trip in the area. Ashley was also very easy to communicate with
Guest favourite
Home in Rindge
4.93 out of 5 average rating, 27 reviews

The Shoreline

FendyRating, 5 stars3 weeks ago
I had a wonderful stay at this beautiful lakehouse !The home is cozy and well-kept, with stunning big windows overlooking the lake. Even though it was winter and we couldn’t fully take in the view, I can only imagine how breathtaking it must be in the summer. The host was incredibly responsive and quick to answer any questions I had, making the stay even more enjoyable. I can’t wait to come back in the warmer months to experience the lake in all its glory! Highly recommend this spot for a peaceful getaway.
Superhost
Home in Winchendon
4.75 out of 5 average rating, 4 reviews

The Perfect Spot at the Lake @ Tatum's Place

AshleyRating, 5 stars1 month 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 stars4 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!!
Home in Fitzwilliam
New place to stay

Seasonal Camp with Amenities!

Weekly house rentals

Top guest favourite
Home in Walpole
5 out of 5 average rating, 70 reviews

Walpole NH Peaceful Farmhouse Getaway-VT/NH Border

LoribethRating, 5 stars5 months ago
Stunning property with beautiful views and tons of charm. Very warm and friendly quintessential New England farmhouse.
Top guest favourite
Home in Northfield
5 out of 5 average rating, 8 reviews

Minimalist forest retreat

JoseRating, 5 stars6 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!
Top guest favourite
Home in Walpole
4.94 out of 5 average rating, 17 reviews

Country Cottage

JiayiRating, 5 stars1 month ago
Great place to stay! Sean is really responsive. His place is exactly as he described—cozy and full of character with a charming vintage feel. Despite its age, the house is well-equipped with everything you need for a comfortable stay. Perfect for a short visit or exploring the city. Would definitely recommend!
Superhost
Home in Fitzwilliam
4.84 out of 5 average rating, 76 reviews

Covey House Retreat with Sauna/Red Light/Biomat

AlexanderRating, 5 stars3 months ago
Absolutely wonderful Airbnb! Clare and Allen were able to accommodate a very last minute check-in due to me being in the area for work at the last minute. Even during a pretty bad snow storm! I would definitely stay here again :)
Superhost
Home in Town of Rockingham
4.86 out of 5 average rating, 76 reviews

Beautiful Victorian Home

RyenRating, 5 stars3 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 😊
Top guest favourite
Home in Rindge
5 out of 5 average rating, 82 reviews

The Crowcroft House

JoyRating, 5 stars2 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.
Guest favourite
Home in Rindge
5 out of 5 average rating, 21 reviews

Changes in Attitude

KatherineRating, 5 stars5 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!

Private house rentals

Guest favourite
Home in Nelson
5 out of 5 average rating, 7 reviews

The Boat House on Granite Lake

PatriciaRating, 5 stars4 weeks ago
Jennifer was a great host. She was always responsive and helpful. The house is as pictured and comfortable. The view is beautiful and it's so peaceful. There's nothing better than a hot cup of coffee watching the sunrise too! It's absolutely incredible! The price is fair and her cleaning fee is only $100, nothing outrageous like other rentals! My only suggestion would be to update the coffee maker. It's not good quality and seems old. For someone like me, starting your day off with good cup of coffee is magical! :)
Top guest favourite
Home in Rindge
5 out of 5 average rating, 37 reviews

Lake house on walking trail near mountain

KavanRating, 5 stars1 month ago
Our stay at was truly wonderful, and the place was absolutely beautiful. We visited during the winter, and the snow blanketing the area transformed everything into a picturesque winter wonderland. The accommodation itself was clean and spacious, providing us with a comfortable and relaxing retreat. The surrounding area offered plenty of wonderful things to do, making our stay even more enjoyable. Rindge's natural beauty, enhanced by the snowy landscape, created a magical atmosphere perfect for outdoor activities and scenic drives. Can't wait to visit again!
Home in Putney
4.83 out of 5 average rating, 6 reviews

Charming 4-bedroom house

MaryRating, 5 stars4 weeks 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!
Guest favourite
Home in Rindge
5 out of 5 average rating, 7 reviews

Divol Pond Cabin

MichaelaRating, 5 stars5 days ago
They where amazing. Very responsive and very sweet. The house was amazing. So peaceful!
Home in Windsor
4.71 out of 5 average rating, 58 reviews

Spacious, Sunny Lake House! Close to ski trails.

GloriaRating, 5 stars5 months ago
We had a great stay! Clean space and easy to find. Had everything we needed. We didn't use the golf cart or explored the area itself, but it was a great place for us to rest. Happy to book again!
Guest favourite
Home in Dublin
5 out of 5 average rating, 13 reviews

Modern Cottage / Farmhouse

JoyRating, 5 stars1 month ago
Beautifully renovated home in a peaceful and serene location that was perfect for my family of four and my MIL with mobility challenges thanks to a first floor bedroom and bathroom with walk in shower. We didn’t need the kitchen for cooking but it had all needed and necessary items if we had wanted to. The entire home was comfortable and cozy - the radiant flooring throughout the house and in the entryway mudroom was amazing. We also didn’t need to use the washer and dryer while we were there, but it was nice to know it was available if needed. In general, most of the rooms were much larger than what you see in the photos - especially the kitchen and dining areas. The table and island with stools allowed my kids to spread out and do school work using the home’s WiFi (no challenges at all with speed or access). Emily was easy to communicate with and quick to respond, which I appreciated. Family loved the location and we’ll add it to the list for return trips to the area.
Guest favourite
Home in Fitzwilliam
5 out of 5 average rating, 6 reviews

Waterfront House on Private Lake - Amazing Sunsets

PaigeRating, 5 stars5 months ago
We loved staying at the lake house! It was so lunch a beautiful setting; Rob and Pam were incredibly friendly and responsive. The house was cozy and fantastic, ready to go for us, and nice and clean. Lots provided- beach towels, fishing rods, local maple syrup & smores supplies. We had a magical cozy fall weekend, Would 100% stay again, and hope to!

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