Vacation 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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Superhost

Home in Winchendon

4.96 out of 5 average rating, 26 reviews

Amazing Lakefront Home with Pool- Tatum's Place

ShawnRating, 5 stars2 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!

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!!

Camper/RV in Dummerston

Airstream Atlas

Ever wonder what it would be like to stay in an Airstream Atlas? This is your chance. This exquisite B-Plus RV has a queen size bed, all bedding, TV with cable, Wifi, AC/Heat and 2 comfortable chairs. The small kitchen is complete with a gas cooktop, microwave, K-cup coffee maker and is stocked with all the cooking tools you will need. The bathroom has a full shower, toilet, sink with vanity and towels. Outside you will find a fire pit, with two chairs and a picnic table. NO PETS permitted.

Top guest favorite

A cozy log cabin is nestled in the woods, featuring a welcoming front porch. Surrounding a circular fire pit made of bricks, four red Adirondack chairs are positioned on a gravel area, offering a perfect spot for evening gatherings.

Cabin in Stoddard

4.93 out of 5 average rating, 117 reviews

Rocky Ledge at Highland Lake: Cozy 3BR Log Cabin

Nestled within the woods of Stoddard, NH, Rocky Ledge is a peaceful year-round family retreat. Our cozy log cabin has 3 bedrooms, 2 bathrooms, and a lower-level den perfect for family time. Enjoy outdoor dining on the large 3-sided deck, and cap off your days with s'mores sessions at the fire pit! Boating, hiking, swimming, and skiing are minutes away. Or, get cozy indoors and enjoy movies, puzzles, and games. Rocky Ledge is pet-friendly! We welcome up to two dogs with a flat $50 pet fee.

Top guest favorite

A panoramic view captures the vibrant green landscape, trees, and colorful flowers under a bright blue sky. Mountains are visible in the distance, enhancing the tranquil outdoor setting, which includes a sparkling pool surrounded by lush gardens that invite relaxation.

Cabin in Windsor

5 out of 5 average rating, 16 reviews

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

Escape to Sunset Cabin at Mountain Ledge, with breathtaking mountain views from almost every part of this stunning cabin! Perfect for couples, families & groups alike, this spectacular log home comfortably accommodates up to 10 guests, featuring cathedral ceilings, 3 bedrooms, 2 bath, 2 living rooms, beautiful kitchen, laundry, pool, firepit, propane grill & multiple walkouts to covered gated wrap-around porch, w/ incredible mountain views! *Gorgeous* western sunset views each night!

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!

This seasonal camp offers the perfect retreat for families and pet owners looking for a relaxing yet adventurous getaway. Nestled in a serene setting, it provides easy access to a peaceful pond and beach area where you can enjoy leisurely kayaking and paddle boating or simply take in the views of beautiful Mt.Monadnock. Equipped with a fire pit for cozy gatherings and a shared pool for swimming and lounging. A golf cart is available for you to explore at your own pace!

The Airstream is positioned in a wooded area, surrounded by tall trees with green foliage. The metallic exterior reflects natural light, creating a striking visual. The ground is covered with brown earth, providing a rustic camping atmosphere.

Camper/RV in Dummerston

4.82 out of 5 average rating, 57 reviews

Airstream Getaway at Full Service Campground

Located on the grounds of the full service Kampfires Campground, this modern Airstream is the perfect way to camp in style. Our custom Airstream has a comfortable queen bed, modern bath with shower, kitchen and dining area. You'll find a fire-ring, an outdoor dining area with a picnic table and private parking area for your vehicle. Enjoy all of the campground amenities like our pool, wifi, game room and even miniature golf!

An outdoor deck is showcased with a dining table and several chairs surrounded by a wooden fence. The cabin's exterior is visible in the background, featuring large windows and a welcoming entrance. Surrounding greenery adds a natural touch to the space.

Cabin in Dummerston

New place to stay

Moose Mansion with Paw Pen at Brattleboro KOA

Unpack and unwind in this spacious, fully equipped deluxe cabin. With AC/heat, a full-size fridge, propane grill, and 3 TVs, it’s stocked with the essentials so you can travel light and stay comfortable—whether it’s for the weekend or a full week. This accommodation is pet friendly for an additional fee. Kick back and stream comfortably with high-speed WiFi available right in your cabin.

The interior of a log cabin features a wooden beamed ceiling and walls. A round table with four chairs occupies the center, while a bunk bed and a full bed are positioned against the walls. Windows adorned with patterned curtains allow natural light to illuminate the space.

Cabin in Dummerston

Log Cabin at Brattleboro North KOA

An idyllic Vermont log cabin at Brattleboro North KOA. With room for up to five guests, including your furry friends, our cozy retreat features a full bed and a bunk with a twin and a full mattress. Stay comfortable all-season with a mini split air conditioner/heater. Experience rustic charm and access to all of the amenities including pool, playgrounds, general store, and arcade.

Two vintage cottages are displayed, each featuring a green metal roof and white exterior. A propane grill is positioned in the foreground, alongside a fire pit and picnic table. Lush green grass surrounds the cottages, providing a natural outdoor setting.

Cabin in Dummerston

Vintage Cottage at Brattleboro North KOA

Your Vermont vacation at Brattleboro North KOA will never be the same once you've stayed in a vintage cottage. Built-in 1954 this cozy cottage has two bedrooms making it the best home base for families! Don't leave anyone behind, this cottage is pet-friendly. AC/Heat, Premium WIFI, Propane Grill, and a mini fridge are included with this accommodation.

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Popular amenities for Cheshire County rentals with a pool

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House rentals with a pool

Superhost

Home in Winchendon

4.96 out of 5 average rating, 26 reviews

Amazing Lakefront Home with Pool- Tatum's Place

ShawnRating, 5 stars2 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!

Guest favorite

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

4.93 out of 5 average rating, 212 reviews

The Brick House on Washington Street

CarolRating, 5 stars1 day ago

My daughter and her husband with adult sitters stayed here to attend a wedding. Some of us stayed at the Downtown Marriott. They have three small children and enjoyed the pool. House was nice and in a great location to downtown .

Superhost

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

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!!

Home in Fitzwilliam

Seasonal Camp with Amenities!

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Vacation rentals with a pool in Cheshire County

Top-rated rentals with a pool in Cheshire County

Vacation rentals for every style

Popular amenities for Cheshire County rentals with a pool

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