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Vacation rentals in Cheshire County

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Top-rated vacation rentals in Cheshire County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Social Distance in Separate 2 Bedroom Guest Suite
SUPERHOST
Entire guest suite · 4 guests · 4 beds · 1 bath

Social Distance in Separate 2 Bedroom Guest Suite✓ Two Blocks from Downtown Keene ✓ Self Check-in Keyless Entry ✓ Walk to Restaurants, Cafes and Shops ✓ Two Bedrooms, One Bathroom and Beverage Center ✓ Wifi and Smart TVs with Local Channels. ✓ Complimentary Filtered Water, Snacks, Tea and Coffee. To accommodate guests looking to social distance, the house has been separated into two living areas. Guests enter the front door to their private guest suite on the 2nd floor. We enter the back door and our living space is on the first floor.

The Carriage House in Historic Fitzwilliam
SUPERHOST
Entire guesthouse · 2 guests · 1 bed · 1 bath

The Carriage House in Historic FitzwilliamWelcome to the Carriage House! Former site of the popular Hannah Davis House Bed and Breakfast, this gorgeous space is ready for your visit! Beautiful wood beams throughout, a cozy loft bedroom, and a completely separate entrance for privacy. Short rides to Rhododendron State Park, Mount Monadnock, Gap Mountain, the Cheshire Rail Trail, Laurel Lake, and many more outdoor activities year round. Walking distance to the town common in a town where little has changed and history is preserved.

Highland Haus- Cozy A-Frame Cabin with Wood Stoves
SUPERHOST
Entire chalet · 4 guests · 2 beds · 1 bath

Highland Haus- Cozy A-Frame Cabin with Wood StovesLooking for the perfect winter get-a-way? The Highland Haus is your answer! Cozy 1975 A-frame chalet cabin sleeps 4 with a comfortable living space, two wood stoves, and a full kitchen. Located in the rural quiet lake community of Stoddard. Enjoy the peace and quiet that this area has to offer. Many local hiking options are available. It is less than a 2-hour drive from Boston to the Highland Haus! Follow and tag us on Instagram- highlandhausnh

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Popular amenities for Cheshire County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Cheshire County

SUPERHOST
  1. Entire cabin
  2. Nelson
Granite Lake New Hampshire Waterfront Cottage
SUPERHOST
  1. Entire apartment
  2. Vernon
Farm land view.
SUPERHOST
  1. Entire guest suite
  2. Winchester
Stay at a craft brewery - Winchester NH
  1. Entire apartment
  2. Keene
Beautiful & unique apartment; walk to downtown
  1. Entire cabin
  2. Stoddard
Cozy New Hampshire cabin with lake access
SUPERHOST
  1. Yurt
  2. Putney
Vermont Retreat Yurt, a restorative escape
SUPERHOST
  1. Entire house
  2. Rindge
Charming Lake Front Home
  1. Entire cabin
  2. Marlborough
Don’t judge a book by its cover!
  1. Entire apartment
  2. Peterborough
Bright and lovely in-town apartment
SUPERHOST
  1. Entire cabin
  2. Stoddard
Cozy Comfort on 250 Acre Private Estate
  1. Entire cottage
  2. Winchendon
Little Camp
SUPERHOST
  1. Entire guest suite
  2. Peterborough
Meadow View