Vacation rentals with a pool in Cheshire County

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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 favorite

Home in Jaffrey

5 out of 5 average rating, 6 reviews

Sunset mountain Retreat

This stylish huge house in Jaffrey, NH is perfect for those who want to relax and unwind nestled within a few short miles of our local treasure Mount Monadnock and Shattuck Golf Course. With a stunning Mountain View, 5 bedrooms (2 king beds, 2 queens and 2 twins), 3 full baths and a huge backyard pool. Close to grocery stores (Shaws, Market Basket and Hannafords) and delicious local restaurants. 70 miles west of Boston Mass in the beautiful Monadnock NH area. Perfect resort-like feel to relax.

Superhost

Home in Winchendon

4.92 out of 5 average rating, 13 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 5 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!

Guest favorite

Cabin in Stoddard

4.91 out of 5 average rating, 90 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.

Guest favorite

Cabin in Windsor

5 out of 5 average rating, 15 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

4.69 out of 5 average rating, 16 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 favorite

Home in Keene

4.93 out of 5 average rating, 205 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.

Guest favorite

Home in Rindge

4.91 out of 5 average rating, 23 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 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 500 ft of beautiful shoreline.

Camper/RV in Dummerston

4.83 out of 5 average rating, 58 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!

Guest favorite

Farm stay in Jaffrey

5 out of 5 average rating, 26 reviews

Comfy Quarters Suite 2 Saltbox Hideaway

This is a brand new suite, designed and built by Mark. All the wood is reclaimed barn boards. Nicely designed with handmade bedside tables, bathroom fixtures and an antique wood cookstove converted to electric with a retro refrigerator. It is a second story suite with a beautiful panoramic view of the eastern sky.