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

Superhost
A light-filled living area features a comfortable sectional sofa, two accented chairs, and a wooden sideboard. A large television is mounted on the wall opposite the seating. Windows allow natural light to fill the space, enhancing the cozy ambiance.
Home in Winchendon
4.75 out of 5 average rating, 4 reviews

The Perfect Spot at the Lake @ Tatum's Place

AshleyRating, 5 stars2 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 stars5 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 stars3 days 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 favorite
A two-story lakefront home is situated on a lush green lawn, visible from the water. The structure includes multiple decks and large windows. A floating dock with chairs is seen in the foreground, while the surrounding trees provide natural scenery.
Home in Antrim
4.97 out of 5 average rating, 79 reviews

The Cozy Place

LauraRating, 5 stars3 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!
Top guest favorite
A wooden cabin is situated on a grassy area surrounded by trees, featuring a spacious deck with steps leading to the entrance. The roof is metal, and multiple large windows allow natural light to illuminate the interior.
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 favorite
A sunlit living room features a wood stove surrounded by natural wood flooring. A rocking chair sits beside a dark trunk, while a lamp and a vase of flowers add warmth. Two large windows provide ample light, and a cozy sofa is positioned nearby.
Home in Brattleboro
4.77 out of 5 average rating, 22 reviews

Eco Friendly Garden House

NeilRating, 5 stars3 months ago
Our stay at Lissa’s was absolutely wonderful! The house was ideal for two couples to enjoy time together comfortably. Its convenient location near town makes it an easy stroll in warmer weather. We highly recommend it and would gladly stay again!
Top guest favorite
A bright living area is featured with a modern fireplace and a wall-mounted television. A low wooden coffee table is centered on a light-colored area rug. A cozy armchair and side table complement the space, along with a small plant positioned near a window.
Home in Rindge
5 out of 5 average rating, 82 reviews

The Crowcroft House

JoyRating, 5 stars3 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
A serene view of a private dock situated on the calm waters of Contoocook Lake, framed by tall trees. A small boat is tied to the dock, with a gentle shoreline visible in the background, creating a peaceful lakeside atmosphere.
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 favorite
The living area is characterized by wooden sliding barn doors leading to two separate bedrooms. A round wooden coffee table sits at the center, complemented by a patterned area rug. Natural light filters through soft curtains, enhancing the open and inviting space.
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
The living room features a comfortable gray sofa facing a TV mounted on a wooden stand. A wooden coffee table is centered on a patterned area rug, and a large abstract painting adorns the wall above the couch. A doorway leads to the dining area.
Home in Troy
4.78 out of 5 average rating, 41 reviews

Monadnock 4-Bedroom Charmer by Cheshire Rail Trail

DzmitryRating, 5 stars2 months ago
Best stay in this area, thanks
Top guest favorite
A spacious sunroom is furnished with multiple seating areas, featuring comfortable wicker chairs and a central glass-top table. Natural light filters in through the screened walls, creating a bright atmosphere. An area rug with a striped pattern adds texture to the wooden floor.
Home in Stoddard
5 out of 5 average rating, 10 reviews

Water views, 2 min to public beach, 4 bedrooms

NicoleRating, 5 stars1 month ago
We were very pleased with the beautiful house. We were there for a girls weekend and just looking to stay in and relax for the weekend and this was just perfect for that. I will definitely book this house again!!

Private house rentals

Guest favorite
A serene evening view of Granite Lake is showcased, with a vibrant sunset reflecting on the water's surface. Silhouetted against the colorful sky, a small dock is visible, extending into the lake, and a few boats can be seen leisurely floating in the distance.
Home in Nelson
5 out of 5 average rating, 9 reviews

The Boat House on Granite Lake

MagaliRating, 5 stars3 days ago
We had a wonderful weekend stay at the Boat House on Lake Granite! The house is right on the water, and the views from the living/dining area were stunning—we ended up eating most of our meals there just to enjoy the scenery. The neighborhood was very cute and quaint, especially in the low season. The lake's circumference is about 3 miles, which makes for perfect morning runs. The kitchen was fully stocked with all the amenities we needed for cooking, and there were two large refrigerators (though we only needed one). The décor was cozy and calming, and the beds were incredibly comfortable. Jen was the perfect host—super responsive and provided very helpful check-in information. We had an excellent stay and are looking forward to returning during the warmer months to enjoy all the summer lake activities!
Top guest favorite
An aerial view captures the classic farmhouse nestled within lush green fields and surrounded by trees. A red barn with a metal roof is visible nearby, and the expansive landscape extends towards distant mountains, showcasing the serene rural setting.
Home in Walpole
5 out of 5 average rating, 70 reviews

Walpole NH Peaceful Farmhouse Getaway-VT/NH Border

LoribethRating, 5 stars6 months ago
Stunning property with beautiful views and tons of charm. Very warm and friendly quintessential New England farmhouse.
Top guest favorite
A quaint cape house is set against a lush green lawn, showcasing a charming red door as the focal point. Symmetrical windows with dark shutters frame the front, while garden elements add natural beauty to the inviting exterior.
Home in Walpole
4.89 out of 5 average rating, 18 reviews

Country Cottage

JiayiRating, 5 stars2 months 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
A welcoming front porch features white railings and seasonal decorations. Colorful plants and flowers are arranged in front, including a bicycle leaning against the railing. The entrance is surrounded by a well-maintained garden with a mix of greenery and rocky landscaping.
Home in Fitzwilliam
4.84 out of 5 average rating, 76 reviews

Covey House Retreat with Sauna/Red Light/Biomat

AlexanderRating, 5 stars4 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
The exterior of a large Victorian house is framed by a tall, green hedge, providing privacy. The building features a cheerful yellow facade with decorative trim and a three-story design. Lush trees and blooming flowers can be seen in the background, contributing to a peaceful environment.
Home in Town of Rockingham
4.86 out of 5 average rating, 76 reviews

Beautiful Victorian Home

RyenRating, 5 stars4 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 😊
A large, two-story home is nestled among lush greenery, surrounded by tall trees. A wide front porch invites relaxation, while multiple windows provide natural light. The well-maintained lawn features an arrangement of plants and a stone pathway leading to the entrance.
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!

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