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Vacation rentals in Chesterfield

Vacation rentals in Chesterfield

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesterfield

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

  • Charming Apt in Beautiful New England Setting
    SUPERHOSTEntire flat · 2 guests · 1 bed · 1 bathroom
    Charming Apt in Beautiful New England Setting

    A private apartment nestled in wooded seclusion just minutes from Brattleboro. Truly the best of both worlds! Easy access to I-91, Brattleboro, and Keene. Easy access to Spofford Lake and many wonderful hiking options.

    What guests are saying:

    “Courtney's apartment was clean, very easy to find and the amenities were perfect. My husband and I stayed here for the weekend to attend a wedding, and the bed was so comfortable (especially since we spent the week prior tent camping in Vermont)! Even though the apartment is attached to a home, it felt very private, which we loved. We would stay here again in a heartbeat! Thanks for providing such a great space, Courtney!”

  • BRAD's Private lakeside retreat in the forest
    SUPERHOSTEntire cabin · 10 guests · 11 beds · 2 bathrooms
    BRAD's Private lakeside retreat in the forest

    A private lakeside retreat on Lake Spofford that comfortably could sleep 14 adults. Loads of privacy amongst the trees with great lake views from every room and from the large sweeping deck. The main house sleeps 10 with two bathrooms to share. There are two quaint lakeside cottages with an adjacent outdoor fireplace and balcony that sleep six. Enjoy fishing, skiing and kayaking in the crystal clear water off your private dock. (7 kayaks/1 canoe) You could BYOBoat, if you like. No pets

    What guests are saying:

    “From the very start, Brad was an excellent host! Above par communication and always available. He even helped me find the lockbox because I arrived at night! His home is in the most beautiful location! A scenic drive through to the road and a quiet peaceful neighborhood. The house itself was immaculately clean and beautifully decorated. The small touches were perfect for our family. There are books, games and TV. WiFi worked extremely well! Very comfortable beds in every room. The two cabins by the water are very cute and comfortable as well! We were absolutely amazed by the water itself. It is clear and wasn’t too cold to swim no matter what time it was. The patio by the water provided us with the perfect place to lounge and make S’mores with the kids! We were able to canoe and kayak together as well. Couldn’t ask for a better time!! We had the most amazing vacation and are planning on coming back next year!”

  • Airstream Getaway at Full Service Campground
    Campervan/Motorhome · 2 guests · 1 bed · 1 bathroom
    Airstream Getaway at Full Service Campground

    Located on the grounds of the full service Kampfires Campground, this modern Airstream is the perfect way to camp in style. Our custom Airstream has a comfortable queen bed, modern bath with shower, kitchen and dining area. Outside in your tree covered corner of the campground you'll find a fire-ring, an outdoor dining area with a picnic table and private parking area for your vehicle. Enjoy all of the campground amenities like our pool, wifi, game room and even miniature golf!

    What guests are saying:

    “The Airstream, Kampfires, and Amy were all wonderful. The camper itself was just incredible. I particularly liked that the stereo could be played throughout, could be heard at a decent volume at the picnic table, and had a USB connection cable. Fully equipped, and I didn't feel like I needed anything else. The grounds were very well kept and easy to navigate. Amy was responsive before my arrival and answered any questions or issues I had once there. My only regret is that I didn't find this place earlier. I would love to plan another trip back! Thank you so much!”

Holiday rentals for every style

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Popular amenities for Chesterfield holiday rentals

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

Other great holiday rentals in Chesterfield

Majestic Mountain View’s
SUPERHOSTEntire house
Majestic Mountain View’s
Price:€169 / night
Beautiful rustic woods and fields retreat for two.
Entire cabin
Beautiful rustic woods and fields retreat for two.
Price:€55 / night
Charming Country Home
SUPERHOSTEntire house
Charming Country Home
Price:€106 / night
Magical Lake Cabin
Entire cabin
Magical Lake Cabin
Price:€89 / night
Tiny Art House - Free Spa Pass* - Dogs Welcome!
SUPERHOSTEntire cabin
Tiny Art House - Free Spa Pass* - Dogs Welcome!
Price:€62 / night
Cottage Style Motel on Spofford lake.
Private room
Cottage Style Motel on Spofford lake.
Price:€81 / night
Charming studio in renovated 19th century church.
SUPERHOSTEntire guest suite
Charming studio in renovated 19th century church.
Price:€67 / night
Quiet, Cozy & Great location for exploring VT !
SUPERHOSTEntire flat
Quiet, Cozy & Great location for exploring VT !
Price:€61 / night
Varykino Cottage @ 252 Sunset Road, Fitzwilliam NH
SUPERHOSTEntire house
Varykino Cottage @ 252 Sunset Road, Fitzwilliam NH
Price:€92 / night
Two Bedroom Garden Suite on the West River
SUPERHOSTPrivate room
Two Bedroom Garden Suite on the West River
Price:€53 / night
Grateful Gait Farm
SUPERHOSTEntire flat
Grateful Gait Farm
Price:€129 / night
Rice Farm Retreat
SUPERHOSTEntire flat
Rice Farm Retreat
Price:€79 / night
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