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House holiday rentals in Cheshire County

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Top-rated house rentals in Cheshire County

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Home in Putney

4.86 out of 5 average rating, 134 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 favourite

Home in Antrim

4.98 out of 5 average rating, 151 reviews

Relaxing Hot Tub Getaway

Come stay at our secluded fully renovated historic home with all new Samsung appliances & furniture. All the necessities for a long or short stay with fully stocked kitchen. A mile from Gregg Lake Beach Professionally cleaned 24/7 Property Manger High speed WiFi ALL YEAR PRIVATE/SECLUDED HOT TUB Fire Pit, Grill, Hammock, Gym equipment Life Size Janga, Yahtzee,Darts,Corn Hole Electric Heating/cooling each room 2 KING PURPLE mattresses 55' Amazon Fire TV 4K in Living Room Vizio 55’ TV in Bedroom

Guest favourite

Home in Putney

4.94 out of 5 average rating, 348 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 Chesterfield

4.92 out of 5 average rating, 88 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.

Home in Town of Rockingham

4.89 out of 5 average rating, 113 reviews

Beautiful Home in the Mountains - The Fox & Owl

When you walk into the Fox and Owl, your stress and anxiety get left outside! The Fox and Owl is perfect for couples and solo adventurers alike - anyone who wants a cozy house in a perfect location for exploring everything southern Vermont has to offer: Hiking, kayaking, skiing, snow-shoeing, bicycling (road, mountain, fat tire), bird and foliage watching, antique and craft shopping, farmers markets and breweries, great local food and great local fishing are all within just a few miles!

Home in Fitzwilliam

4.84 out of 5 average rating, 58 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

Guest favourite

Home in Keene

4.93 out of 5 average rating, 188 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 Winchester

5 out of 5 average rating, 5 reviews

Dragonfly Cottages: A Sweetwater Stay

New Pictures coming soon! Dragonfly cottages is a main house with 2 bedrooms and a full kitchen and bath, and two small cottages. A rushing river runs through it 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 a additional $45 per night each, billed separately through Airbnb after your reservation is booked.

Guest favourite

Home in Keene

5 out of 5 average rating, 19 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 favourite

Home in Brattleboro

4.94 out of 5 average rating, 104 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 Alstead

5 out of 5 average rating, 22 reviews

The Lake House

Relax with friends or family at this peaceful place to stay. Outfitted with two porches, space for four guests, and plenty of privacy. A beautiful spot, ideal for a vacation on the lake. Swim, kayak, explore the island, or just relax on the porch with your favorite drink. You will find this quiet get-a-way home has everything you need.

Guest favourite

Home in Chesterfield

4.97 out of 5 average rating, 235 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.

Holiday rentals for every style

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Flats

Convenient locations with everyday essentials

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Popular amenities for house rentals in Cheshire County

Free parking on premises

Air conditioning

House rentals with a pool

Home in Winchendon

The Perfect Spot at the Lake @ Tatum's Place

Home in Surry

4.71 out of 5 average rating, 34 reviews

Bright, Large, Spacious Family Home

Home in Rindge

New place to stay

The Shoreline

Home in Troy

5 out of 5 average rating, 3 reviews

Mountain View escape

Home in Keene

Dog friendly, Immaculate!

Home in Winchendon

Amazing Lakefront Home with Pool- Tatum's Place

Weekly house rentals

Guest favourite

Home in Keene

4.98 out of 5 average rating, 44 reviews

Winfield & Boots Downtown Retreat

Guest favourite

Home in Keene

4.96 out of 5 average rating, 55 reviews

Keene Center Farmhouse: Large & Cozy + Hot Tub

Guest favourite

Home in Swanzey

4.92 out of 5 average rating, 25 reviews

Hillside Haven: Luxe Farm Escape | 5BR-2 King Beds

Guest favourite

Home in Rindge

5 out of 5 average rating, 81 reviews

Waterfront escape

Guest favourite

Home in Keene

4.95 out of 5 average rating, 40 reviews

Ultimate Family Vacation Home

Guest favourite

Home in Walpole

5 out of 5 average rating, 66 reviews

Walpole NH Peaceful Farmhouse Getaway-VT/NH Border

Guest favourite

Home in Jaffrey

4.75 out of 5 average rating, 12 reviews

A True New England experience -full kitchen

Guest favourite

Home in Keene

4.9 out of 5 average rating, 68 reviews

Sweet Home

Private house rentals

Guest favourite

Home in Spofford

5 out of 5 average rating, 8 reviews

A-Frame Cottage at Lake Spofford

Guest favourite

Home in Hillsboro

5 out of 5 average rating, 22 reviews

Your private lake retreat awaits

Guest favourite

Home in Hillsboro

4.87 out of 5 average rating, 15 reviews

Cottage -Lake and ski!

Guest favourite

Home in Hancock

4.94 out of 5 average rating, 80 reviews

Large Home in Peaceful Historical Village

Home in Putney

4.9 out of 5 average rating, 10 reviews

Beautiful 5-Bedroom Country Home with Home Theater

Guest favourite

Home in Rindge

4.86 out of 5 average rating, 7 reviews

Cottage Cove lakefront home

Home in Spofford

4.88 out of 5 average rating, 59 reviews

Main House

Guest favourite

Home in Walpole

4.98 out of 5 average rating, 62 reviews

Charming, Large House in Walpole NH /VT. Border

Destinations to explore