House vacation rentals in Cheshire County

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Top-rated house rentals in Cheshire County

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Guest favorite

Home in Putney

4.88 out of 5 average rating, 172 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)

Guest favorite

Home in Putney

4.94 out of 5 average rating, 370 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.

Superhost

Home in Chesterfield

4.9 out of 5 average rating, 103 reviews

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, betweeen Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. It’s 15 minutes to Brattleboro, 5 minutes to the boat ramp on the 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.

Superhost

Home in Fitzwilliam

4.85 out of 5 average rating, 74 reviews

The Covey House with Infrared Sauna

Escape the City & enjoy the tranquility of this beautiful sanctuary. Enjoy a romantic get away to reconnect with your spouse, take a sabbatical, spend time alone, or turn it into a healing retreat & add on some Covey House frequency treatments. High speed internet makes it perfect for remote work. Nestled in the center of Fitzwilliam, overlooking the village green it is the gateway to the beautiful Monadnock Region close to mountains, hiking trails, pristine lakes & tax free shopping

Superhost

Home in Antrim

4.84 out of 5 average rating, 112 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 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 Keene

5 out of 5 average rating, 117 reviews

Downtown Hot Tub Escape

Relaxing Escape in central Keene. Walking distance from downtown but just far enough to be quit for a comfortable stay. Also across the street from Keene Ice Hockey Rink HOT TUB OPEN YEAR AROUND 24/7 IN PRIVATE GAZEBO FIRE PIT & Hammock, Games Renovated fully stocked Kitchen, wine cooler 3 PURPLE Queen Beds & 1 Twin Sleeps up to 12ppl 2 Flat screen fire TVs HIGH SPEED WIFI Professionally Cleaned All necessities for a long or short stay Electric Heating/cooling each room

Guest favorite

Home in Putney

4.89 out of 5 average rating, 101 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.

Guest favorite

Home in Keene

4.93 out of 5 average rating, 41 reviews

Little House with Lots to Offer

Little House with Lots to Offer. This private house located off Rte 10 is minutes away from downtown and Keene State College. Staying here lets you enjoy the privacy of your own home, the plentiful city of Keene, and the peaceful outdoors NH is known for. Backyard opens up to 2 acres of private trails surrounded by NH State Land. Can sleep 4 with cots for more. Pets welcome! Send a message for any questions. Here to help.

Guest favorite

Home in Winchester

4.92 out of 5 average rating, 25 reviews

Dragonfly Cottages: A Sweetwater Stay

Dragonfly cottages is a main house with 2 bedrooms and a full kitchen and bath, and two small cottages. A rushing river sits behind the property and direct access to lovely Forest Lake is available a short walk away. The main house is included in this rental fee listed, the home office and the cozy A-Frame are an additional $45 per night each, billed separately through Airbnb after your reservation is booked.

Guest favorite

Home in Brattleboro

4.95 out of 5 average rating, 116 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 favorite

Home in Chesterfield

4.98 out of 5 average rating, 253 reviews

Charming Country Home

Charming one level ranch style home. Quiet country neighborhood 5 miles from Keene, NH, 10 miles from Brattleboro, VT. The home has a fully equipped kitchen, smart TVs, spacious rooms, two bedrooms, two full baths, laundry in basement, couple of steps to master bedroom. Great backyard. Spacious driveway with motion lights.