House vacation rentals in Cheshire County

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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 stars4 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
The exterior of the spacious house is shown, featuring a gray facade with multiple windows and a large front yard. Sunlight filters through the trees in the background, casting a warm glow over the lush green grass and surrounding plants.
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars7 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
4.96 out of 5 average rating, 26 reviews

Amazing Lakefront Home with Pool- Tatum's Place

ShawnRating, 5 stars3 days ago
This property and experience was everything and more! From the location on the beautiful lake to the clean bedrooms and common rooms! Plenty of space to entertain everything was clean and modern! The hostess Ashley was very attentive to any questions I had and very friendly! Some places I’ll never return to because of the host. I shall be raving about this place for years to come with memories to accompany them! 10/10 experience for sure!
A rustic metal silhouette of a bear and cub is positioned against a vibrant backdrop of flowers and greenery. The design features trees and mountains, creating an outdoor theme that complements the natural surroundings.
Home in Fitzwilliam

Seasonal Camp with Amenities!

Weekly house rentals

Guest favorite
A welcoming living area features a pair of large windows, allowing natural light to illuminate the space. Comfortable seating includes a dark leather sofa and two rocking chairs. A wooden coffee table is placed in the center, adorned with magazines and decorative items, while the walls are painted in a soft green.
Home in Harrisville
4.94 out of 5 average rating, 34 reviews

The Hemlock House at Aldworth Manor

LindaRating, 5 stars1 month ago
This was the perfect place for a gathering of friends and family from out of town for a wedding at Cobb Hill Estates. It was very convenient to the venue. But it was also a beautiful home, well-equipped for all of our entertaining during the four days of the wedding event. We couldn’t have been happier.
Guest favorite
A serene view of the lakefront home is presented, featuring a sandy beach and a wooden dock extending into the calm waters. Surrounding trees display autumn colors, and the stone-lined shoreline reflects the tranquil lake, creating an inviting atmosphere for relaxation.
Home in Rindge
4.94 out of 5 average rating, 36 reviews

Magic Lakehouse, Waterfront, Private Beach & Dock

DestinyRating, 5 stars3 days ago
Fantastic stay, lovely location, well furnished, clean, great communication. Would stay again!
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
4.98 out of 5 average rating, 82 reviews

The Cozy Place

WayneRating, 5 stars1 week ago
Absolutely beautiful location, the lake is about 20ft from the back deck. Quiet, peaceful and sleeping with the slider open allows you to hear the loons; if you've never fallen asleep to the sounds of loons, this is reason enough to book a stay.
Top guest favorite
A large New England home is shown under a twilight sky, with soft snow covering the ground. Illuminated windows provide a warm glow, and the entrance is framed by neatly arranged shrubs and two small trees, creating a welcoming appearance.
Home in Dublin
4.98 out of 5 average rating, 60 reviews

Cobb Meadow House - Cozy 5 Bedroom New England hom

JamesRating, 5 stars2 weeks ago
We had a great time, the place was just like how it was described!
Guest favorite
An outdoor deck features a large wooden dining table surrounded by comfortable chairs, shaded by a spacious umbrella. The setting is bordered by lush greenery, creating a serene atmosphere for outdoor dining or relaxation.
Home in Peterborough
4.95 out of 5 average rating, 95 reviews

Hazelhurst Vacation House

ERating, 5 stars6 months ago
You walk into Eric’s place and it feels like a home thoughtfully set up so that you can just walk in and be comfortable. It’s an “and, breathe” kind of relaxing, homey place. Eric was super responsive to any & all questions we had. We absolutely loved our time there and look forward to rebooking in the future!
Guest favorite
A bright living area features two rattan chairs with blue cushions positioned beside a small table. A stylish dresser stands against a wall with a circular mirror above it. Large windows provide a view of the lake and let in ample natural light.
Home in Chesterfield
5 out of 5 average rating, 13 reviews

Picturesque Lakefront Retreat at Spofford Lake

AnaRating, 5 stars4 weeks ago
This was our second stay at Palmer’s place and we already can’t wait to go back. It always exceeds expectations. Palmer pays close attention to detail, making sure everything you need is within reach. The home itself is absolutely beautiful, matched only by the view of the lake from the main living area. Although it wasn’t quite warm enough for us to enjoy the outside activities, we thoroughly enjoyed relaxing inside, which speaks to how much the home has to offer. If you’re looking for a place to stay, look no further. This is truly a gem.
Guest favorite
A serene landscape showcases rolling hills under a pastel sky at dusk. The calm water reflects the soft hues of purple and pink, while trees frame the view, enhancing the tranquil setting.
Home in Bellows falls
4.9 out of 5 average rating, 10 reviews

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars4 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Superhost
A spacious bedroom features a wooden bed frame with a soft white bedspread and decorative pillows in shades of gold. Two bedside lamps provide warm light, and a decorative wall hanging adds color to the yellow walls. The ceiling is adorned with a stylish chandelier.
Home in Fitzwilliam
4.84 out of 5 average rating, 77 reviews

Covey House Retreat with Sauna/Red Light/Biomat

BernardRating, 5 stars1 month 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!!

Private house rentals

Top guest favorite
A sunlit living area features exposed wooden beams and vibrant orange walls. A comfortable white sofa is complemented by two patterned pillows, while a wooden table sits in front. Nearby windows allow natural light to illuminate the space, accented by green plants and warm lighting.
Home in Putney
4.92 out of 5 average rating, 60 reviews

Beautiful post and beam home by waterfall.

AngelaRating, 5 stars10 months ago
Three of us stayed at Elissa’s as a launch pad for hiking and biking in the area. It’s a beautiful place, the kitchen is well stocked, and the outdoor space is inviting. We enjoyed a nice fire outside and watched the stars come out. We would love to come back in the winter and experience the coziness of the interior wood burning stove.
Guest favorite
The lakefront home features multiple decks overlooking Contoocook Lake, surrounded by lush greenery and tall trees. A staircase leads from the property down to the water's edge, where kayaks and boats are visible at the dock, highlighting access to year-round outdoor activities.
Home in Rindge
4.8 out of 5 average rating, 5 reviews

Lakefront family vacation home

KristenRating, 5 stars1 month ago
We had a wonderful stay at this home! Stephen and Toby were great hosts who were easy to work with. Some of the house has been renovated recently and is beautiful. The house was clean and the views were amazing! We would definitely stay here again.
Top 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, 14 reviews

The Boat House on Granite Lake

KirstenRating, 5 stars1 month ago
I had an absolutely wonderful stay at Granite Lake! The house is gorgeous—beautifully decorated, incredibly comfortable, and stocked with everything you could possibly need. Jennifer was an amazing and responsive host, making the entire experience extremely easy and welcoming. One of the highlights was the 3-mile loop around the lake, perfect for a run or walk. There are also kayaks for some time out on the water. Mornings and evenings should be spent on the porch—reading, sipping coffee or wine, and watching the stunning sunrises and sunsets. This place is truly a slice of peaceful paradise. I can’t recommend it enough and hope to return soon!
Guest favorite
A two-story house is set among lush greenery, with a pathway leading to the entrance. Vibrant yellow flowers border the walkway, while the vehicle is parked in front. A porch with a sloping roof adds charm to the home, surrounded by trees for privacy.
Home in Town of Rockingham
4.87 out of 5 average rating, 71 reviews

Serenity - Fantastic Spacious House In Quaint VT

MeganRating, 5 stars3 months ago
The space is great for larger parties to sit together and enjoy dinner or hanging out. In the center of town yet quiet and felt like home away from home. The fireplace and access to firewood was great. Chris was friendly to communicate with and responded quickly. We were all very happy with our stay
Superhost
The charming Craftsman-style home features a light green exterior with red accents. Large windows allow for abundant natural light, filling the interior. A sloped metal roof complements the design, while surrounding trees and landscaping enhance the serene setting.
Home in Town of Rockingham

Entire Craftsman House Rental

GerryRating, 5 stars57 months ago
A spacious place with character, Rebecca's place had everything we needed, and she was an extremely attentive host. Quiet neighborhood. Being close to I-91 made Rebecca's house an excellent jumping off point for day trips to various places in Vermont.
Top guest favorite
A screened-in porch is shown overlooking the lake, featuring comfortable seating with a blue couch and wicker chairs. Large windows allow natural light to illuminate the space, with trees visible outside. A dining table is positioned nearby, enhancing the relaxation area.
Home in Swanzey
5 out of 5 average rating, 6 reviews

Lake Front Cottage

JordanRating, 5 stars8 months ago
My wife and I escaped to Swanzey for our one year anniversary. When we arrived, Kate knew we were showing up late, so she left lights on and a little dessert + bottle of wine for our celebration. Kate was very responsive, left recommendations for where to go and made this an excellent stay.
Guest favorite
A wooden deck with a railing extends from the entrance of a rustic, two-story cabin. Large windows brighten the facade, and the structure is surrounded by grass and trees. A clear blue sky is visible above, enhancing the cabin's serene setting.
Home in Hillsborough
5 out of 5 average rating, 10 reviews

Very Private Cabin on 12 Acres

MarkRating, 5 stars3 days ago
If you want privacy this place stands out, It was wonderful to have our dog run around on the grounds, a beautiful deck to sit on as well as a nice fire pit. A warm rustic place with plenty of room to enjoy and unwind.
Top guest favorite
Home in Hillsboro
4.98 out of 5 average rating, 42 reviews

Your private lake retreat awaits

GarmaiseRating, 5 stars4 months ago
This house is absolutely gorgeous and also feels very relaxing at the same time. The views from the house of the lake literally take your breath away. Ewa is very responsive and kind. She accommodated us in ways she really didn't need to and we appreciated that so much. Wifi is great at this house, if you need to work or have meetings. However, you may have issues with reception (depending on your carrier) in the area so be sure to write down directions before going! Also the street is really just the driveway and it's not marked so be sure to follow GPS to know when you have arrived! We would stay here again in a heartbeat. It's a great house for 2 families to stay together! And the basement with the pool table and ping pong - wow- what a bonus!!

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