House holiday rentals in Cheshire County

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Top-rated house rentals in Cheshire County

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Guest favourite

Home in Putney

4.89 out of 5 average rating, 210 reviews

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Top Guest favourite

Home in Washington

5 out of 5 average rating, 108 reviews

Newer Home on quiet 200 acre lake - sleeps 6

Less than an hour from Manchester, Concord & Keene, this new home offers relaxation & year-round adventure. This lakefront property has a dock, with kayaks & paddleboards. You could also walk down the paved road to the neighborhood beach & swim platform. About 30 minutes to Pats Peak, Sunapee, or Crotched Mtn ski resorts. Beds for 6, 2 full baths, W/D, fully equipped kitchen, open living space, gas fireplace, water views, gas grill, parking, firepit, internet. We do not allow pets or smoking.

Top Guest favourite

Home in Keene

5 out of 5 average rating, 159 reviews

Downtown Hot Tub Escape

The best outdoor experience in southern NH: HOT TUB OPEN YEAR AROUND 24/7 IN PRIVATE GAZEBO Gorgeous Fire Pit, Hammock, Life size games, swing set Safest/quietest neighborhood in central Keene. Walking distance from downtown Across the street from Keene Ice Hockey Rink close to beaches, hiking trails & ski resorts Renovated fully stocked Kitchen for any chef + wine cooler Luxury PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort

Top Guest favourite

Home in Putney

4.94 out of 5 average rating, 399 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Guest favourite

Home in Keene

4.84 out of 5 average rating, 44 reviews

Cozy Downtown Getaway!

Welcome to our charming Airbnb nestled near downtown Keene, New Hampshire! Our property offers a cozy and welcoming retreat for guests looking to experience the vibrant culture of this historic city. With its convenient location, you'll find yourself just a short stroll away from the bustling shops, eateries, and attractions that downtown Keene has to offer. The spacious Airbnb boasts 3 bedrooms, 2 bathrooms and ample living spaces making it ideal for families or groups of friends traveling.

Superhost

Home in Chesterfield

4.91 out of 5 average rating, 116 reviews

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Superhost

Home in Stoddard

5 out of 5 average rating, 3 reviews

Island Pond Cottage, pet friendly, walk to deli

Sleeps 4-5. Queen bed, Twin bed w/trundle, Full Futon. Cute Cottage in walking distance to boat launch, Island Pond Beach, Country Store/Deli. Pets welcome. Swim or boat at local lakes, explore hiking trails, the Harris Wildlife Center, see Highland cows and buffalo at Pitcher Mountain Farm, or just chill & BBQ at the cottage with a nice beverage by the fire pit. Nice restaurants to visit in Peterborough, Keene, and Jaffery. The little marina on Highland lake is set to reopen this summer.

Superhost

Home in Antrim

4.81 out of 5 average rating, 134 reviews

Quiet House in the Woods

Relax with the whole family at this peaceful place to stay. - Gregg Lake 5 mins away (Swim, Volleyball, Swings, Boat Docks) - Great hiking trails (Monadnock & Miller State Park) - Ski in the winter (Crotched Mountain 20 mins away, Pats Peak 30 mins away) - Small town: Mom & Pop shops/restaurants, Antique stores - 2 Decks: Out door dining & sitting areas This is not an investment property, this is my home. Please be respectful of the property. Thank you! Hope you enjoy your stay!

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.

Guest favourite

Home in Putney

4.9 out of 5 average rating, 106 reviews

Peaceful Beautiful Mountain Home Spectacular Views

15 Spectacular Acres! Plenty of room for the entire family or great for a couples getaway. This home has everything you need. There are brand new mattresses, quilts, linens, towels, cookware, plates and utensils for your comfort. The beautiful mountain views are seen from just about every room. There is a wood burning fireplace, 4 bedrooms and 2 full bathrooms. Both levels have 3 season porches to enjoy the views, coffee, reading or a meal.

Top Guest favourite

Home in Brattleboro

4.94 out of 5 average rating, 125 reviews

Spacious Brattleboro home on river, walk to town

Look no further for the perfect retreat. This spacious area for AirBnB guests (approx 3,000 sq feet) consists of 4 bedrooms, 4 bathrooms (2 en-suite), a formal living room & dining room, a TV-room, and kitchen (eat-in) with family area opening onto a deck. Dramatic river & Wantastiquet Mountain views (foliage or greenery). Ten minute walk to Brattleboro Main Street.

Guest favourite

Home in Walpole

4.92 out of 5 average rating, 24 reviews

A Quaint Setting in the Center of Walpole Village

A classic New England colonial home welcomes you. Recent refurbishments provide a comfortable living space for 1-2 people on the first floor. Located downtown. Walking distance to activities and services including a French Restaurant, adjacent coffee shop, and gourmet market. Golfing, hiking, hang gliding, and skiing are within easy reach.