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Holiday rentals with a pool in Cheshire County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cheshire County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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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!

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!

Top Guest favourite

Cabin in Windsor

5 out of 5 average rating, 15 reviews

*Amazing Mountain Views* log cabin w/ pool+firepit

RobertoRating, 5 stars6 months ago

Daniel and Trisha did such a wonderful job curating an amazing experience in this beautiful home. From small thoughtful amenities like extra chargers in each room, to gifting us a delicious plate of assorted fresh baked goods and everything needed for smores! The inside of the home was absolutely super cozy, spotless, and had a full kitchen. Outside on the porch was where our group witnessed one of the best sunsets we have ever seen! such an incredible view of the landscape that truly took our breath away. Lastly, Daniel and Trisha were very responsive, making sure we had everything we needed as well as providing a ton of hiking and food recommendations. If you are thinking if booking this airbnb, do not think twice!! I cannot speak any more highly of how amazing this home was! We were a group of 11 guys and were comfortable the entire time.

Guest favourite

4.93 out of 5 average rating, 208 reviews

The Brick House on Washington Street

KennethRating, 5 stars2 months ago

We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation

Campervan/RV in Dummerston

4.82 out of 5 average rating, 57 reviews

Airstream Getaway at Full Service Campground

KentonRating, 5 stars33 months ago

I had an amazing time experiencing an Airstream! Great fun! The campground is terrific and I enjoyed live music Friday night with a burger and fries from the food truck. On Saturday I enjoyed a campfire and another burger! Everyone who worked at the campground is very friendly. The location is excellent to explore Brattleboro. I also took a day trip to Woodstock. The Airstream was parked on the edge of an open field in close proximity to another RV. Overall I had a great visit and would recommend!

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!!

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Popular amenities for Cheshire County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

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!

Guest favourite

4.93 out of 5 average rating, 208 reviews

The Brick House on Washington Street

KennethRating, 5 stars2 months ago

We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation

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!

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!!

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