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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Guest favourite

Home in Winchendon

4.97 out of 5 average rating, 29 reviews

Amazing Lakefront Home with Pool- Tatum's Place

Bring the whole family to this great place for fun. Escape to our stunning waterfront property on Lake Monomonac! With 200 ft of lake frontage, a sandy beach, private boat docks, pool, it's the perfect year-round getaway. Enjoy spacious living with many bedrooms,4 baths, and TWO kitchens, Infrared SAUNA. Summer fun includes boating, swimming. In the winter, snowmobiling + skiing. Close to many amenities makes it ideal for families. Book now for unforgettable memories at our paradise by the lake!

Top Guest favourite

Cabin in Stoddard

4.93 out of 5 average rating, 123 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.

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Home in Winchendon

4.75 out of 5 average rating, 4 reviews

The Perfect Spot at the Lake @ Tatum's Place

Bring the whole family to this great place with lots of room for fun. It has 3 very spacious bedrooms and 3 full bathrooms. Shared laundry room. Lots of space to entertain and a beautiful view of Lake Monomonac. It has 200ft of lake frontage and a large back yard. This is available November- April. In the winter, enjoy ice fishing, snowmobiling + skiing . Close to many amenities makes it ideal for families. Book now and experience unforgettable memories at our paradise by the lake!

Top Guest favourite

Cabin in Windsor

5 out of 5 average rating, 23 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!

Home in Troy

4.52 out of 5 average rating, 25 reviews

Mountain View escape

Come enjoy the sunrise views over Mt. Monadnock (2nd most climbed mtn in the world) from the back decks or hot tub. Relax in the sauna. Spend the day hiking some of the hundreds of miles of trails nearby or in picturesque downtown Keene shopping. There's over 20 ski mountains within 30-90 minutes away including Wachusett, Stratton, Mt. Snow, Okemo and Killington. Keene has plenty of dining options and nightlife along with a casino/ sports bar. Keene State college is 11 minutes away

Guest favourite

Home in Keene

4.93 out of 5 average rating, 214 reviews

The Brick House on Washington Street

Three guest bedrooms in a Colonial home on Washington Street make a great launchpad for visitors to Keene. From here, it's a pleasant walk or drive to Downtown restaurants, the theatre and shops. The Sterling family has owned this pretty place since 1982 and a design studio operates in the barn portion of the space. The open living room with TV and original fireplace adjoin a "tea room" with a bright bay window. Family chef-approved, guests are welcome to use the spacious kitchen.

Home in Fitzwilliam

5 out of 5 average rating, 3 reviews

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!

Guest favourite

Home in Rindge

4.94 out of 5 average rating, 33 reviews

The Shoreline

Welcome to The Shoreline. This Classic New England Lakehouse is located on Lake Monomonac, minutes away from amenities but tucked away in small town America. This property is the ideal getaway for a relaxing peaceful vacation. The kitchen and living areas are comfortable and clean, but the real star is the lake itself—perfect for boating, kayaking, swimming, and fishing. Enjoy the 180 degree water views and over 600 ft of beautiful shoreline.

Campervan/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!

Home in Surry

4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

On two acres of green grass, nestled in the trees, with seasonal mountain views is a beautiful big house with plenty of space for all. A quiet and spacious, family friendly home in the country, 10 minutes from main street in downtown Keene. This home has a large living room with comfortable seating, 4 bedrooms, formal dining area, and a large spacious eat in kitchen with additional dining area.

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Cabin in Dummerston

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.

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Cabin in Dummerston

Log Cabin at Brattleboro 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.