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Vacation rentals in Cheshire County

Vacation rentals in Cheshire County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cheshire County

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

  • Honeycrisp Cottage - A Tiny Timber Frame
    SUPERHOSTTiny house · 4 guests · 2 beds · 1 bathroom
    Honeycrisp Cottage - A Tiny Timber Frame

    Honeycrisp Cottage a Tiny Timber Frame is a bright, energy efficient dwelling nestled on 9 acres overlooking a beautiful forested mountain & trails to explore along a brook. A peaceful getaway retreat equipped with a living room, a king bed, loft with a queen bed, full kitchen, & full bathroom. 1 hour from ski resorts. * Please No Smoking On The Property

    What guests are saying:

    “After two months of quarantine, my fiancé and I spent a much needed weekend away at Honeycrisp Cottage. It was the perfect place to unplug and unwind! We enjoyed exploring the trails on the property, playing card/board games and relaxing by the bonfire. Unfortunately a lot of the hiking trails and restaurants in the area remained closed due to COVID-19 but that only means we’ll have to plan another trip back so we can fully experience everything the area has to offer :)”

  • Varykino Cottage @ 252 Sunset Road, Fitzwilliam NH
    SUPERHOSTEntire house · 4 guests · 1 bed · 1 bathroom
    Varykino Cottage @ 252 Sunset Road, Fitzwilliam NH

    My place is close to Keene, NH, Fitzwilliam Inn, Mount Monadnock, Rhododendron State Park. You’ll love my place because of The calm surroundings, shade and sunshine ease of access to everything in the Monadnock Region. My place is good for couples, solo adventurers, families (with kids), and furry friends (pets). Just to be clear the beach is across the road, (which is about 10' wide) and slightly to the left of my house.

    What guests are saying:

    “Dick's place was everything we needed for a weekend getaway - cozy, clean, private, and right next to a beautiful lake with a small and secluded beach. Driving directions were clear, and the cottage had all the essentials one would need. We would love to come back for another getaway.”

  • Grateful Gait Farm
    SUPERHOSTEntire flat · 2 guests · 1 bed · 1 bathroom
    Grateful Gait Farm

    A beautiful private space with gleaming hardwood floors, located on a 100 acre farm in a historic renovated 1830's home only half a mile from downtown Keene. With stunning views of Mount Monadnock, this gorgeous setting offers a wonderful place to relax and enjoy whether you are interested in being around animals or just looking out over a stunning view. A country feel, paired with the ability to walk or bike to downtown Keene, makes this apartment unique and well worth a visit.

    What guests are saying:

    “The farm is truly gorgeous and even more stunning than portrayed here on AirBnB. The property is truly amazing. There is so much to see and do. The animals are all so friendly and well taken care of. Our beagles were in heaven. One of our dogs has severe anxiety as a result of PTSD, like myself from my previous marriage but on the farm she truly came into her own. She sensed how calm and well taken care of the animals are and she was calmer than we’ve ever seen her. She acted like a true beagle for the first time. It was miraculous!”

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Cheshire County holiday rentals

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

Other great holiday rentals in Cheshire County

The Brick House on Washington Street
SUPERHOSTEntire house
The Brick House on Washington Street
Price:€155 / night
Rustic Lakefront Cabin for 6!
SUPERHOSTEntire cabin
Rustic Lakefront Cabin for 6!
Price:€117 / night
NEAR SKI AREA, spacious, private upstairs apt..
SUPERHOSTEntire flat
NEAR SKI AREA, spacious, private upstairs apt..
Price:€76 / night
Charming Lake Front Home
SUPERHOSTEntire house
Charming Lake Front Home
Price:€178 / night
Quiet, Cozy & Great location for exploring VT !
SUPERHOSTEntire flat
Quiet, Cozy & Great location for exploring VT !
Price:€61 / night
Cozy Train Depot in Putney Vermont
SUPERHOSTEntire house
Cozy Train Depot in Putney Vermont
Price:€75 / night
Comfy bedroom in West Keene
SUPERHOSTPrivate room
Comfy bedroom in West Keene
Price:€44 / night
1br private Apt-pets ok- short walk to Main Street
SUPERHOSTEntire guest suite
1br private Apt-pets ok- short walk to Main Street
Price:€66 / night
Bright, quiet, private apartment in central Keene
SUPERHOSTEntire guest suite
Bright, quiet, private apartment in central Keene
Price:€57 / night
Vermont Botanical Studio Apartment
SUPERHOSTEntire house
Vermont Botanical Studio Apartment
Price:€57 / night
PERFECT GETAWAY GOLF & SKI MONADNOCK REGION OF NH
SUPERHOSTEntire house
PERFECT GETAWAY GOLF & SKI MONADNOCK REGION OF NH
Price:€114 / night
The Phineas Handerson House:  The Faulkner Suite
SUPERHOSTEntire flat
The Phineas Handerson House: The Faulkner Suite
Price:€78 / night
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