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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.

  • Just Be Cabin
    SUPERHOSTEntire cabin · 2 guests · 1 bed · Toilet with sink
    Just Be Cabin

    Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

    What guests are saying:

    “Stacey's cabin on her family's property is a wonderfully simple and secluded cabin surrounded by tall trees. The wood stove kept things toasty, the airy living space is beautiful and peaceful. The cabin is at the edge of the forest about 100 feet behind the house and garden. The surrounding area is quiet, beautiful--gravel paths up and down wooded hills, orchards, old stone homesteads and weathered barns. The nearby Old Creamery coop is absolutely fantastic. I pulled up to the house and Stacey was out boiling sap from their sugar maples, and she sent me off with a fresh jar of the most rich, dark maple syrup. I came for just one night to get away from the city and real life, and I was very happy.”

  • Lakefront w/ Private Beach & Kayaks/Canoe
    SUPERHOSTEntire cottage · 6 guests · 5 beds · 1 bathroom
    Lakefront w/ Private Beach & Kayaks/Canoe

    COVID-19 quarantine blues got you down? Safely social distance on your own private beach! Offered for your enjoyment is a quaint 3 season cottage on pristine Hammond Pond with exceptional views and all the amenities that come with waterfront living. We are following CDC recommended guidelines for cleaning to ensure a safe respite for our quarantine-weary guests. ***Please read house rules BEFORE booking (scroll to: "Things to Know"), and notify us if traveling with a pet BEFORE check-in ***

    What guests are saying:

    “What a wonderful space this is! Janna is immediately and pleasantly responsive to all questions or issues. The property is private and the view of the lake is spectacular. We were greeted with a lovely autumnal display on the vast and welcoming screen porch: a vase of fresh flowers, a Day of the Dead succulent planter, and some gourds decorated the table. Janna thoughtfully left dog bowls and dog biscuits to welcome our canine companion. Many items that I did not expect to find were available, such as shampoo/conditioner, laundry detergent, tea and coffee, condiments. There were a variety of pots and pans, utensils, coffee maker, electric kettle, oven/stove, but no microwave, which was only an issue because my arthritic old lady dog needs hot packs warmed up. The bed was comfortable. The bathroom was small for the largest among us, which is fairly common in cabins. Our stay was peaceful and enjoyable. I was taking an art class at Snow Farm not 10 minutes away, so it was immensely convenient. The only unintended complication was my reluctance to spend so much time away from this lovely lake home and Janna's unfailing hospitality.”

  • Riverfront Getaway
    SUPERHOSTEntire house · 4 guests · 2 beds · 1 bathroom
    Riverfront Getaway

    Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

    What guests are saying:

    “Great place to get away from it all! The location along the river is perfect, and I enjoyed spending time on the deck and hot tub taking it all in. Communication was very fast and easy, and the place is exactly as described. The neighbours are friendly, and there are some nice trails within walking distance or a short drive. Would happily stay again.”

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

The Old Parish Hall, right in down town!
SUPERHOSTEntire flat
The Old Parish Hall, right in down town!
Price:€92 / night
A Place for Peace - suite w/full bath
SUPERHOSTPrivate room
A Place for Peace - suite w/full bath
Price:€52 / night
Country Luxury in the Heart of the Berkshires
SUPERHOSTPrivate room
Country Luxury in the Heart of the Berkshires
Price:€57 / night
Goreytastic Private ApARTment @ the EMC
SUPERHOSTEntire guest suite
Goreytastic Private ApARTment @ the EMC
Price:€70 / night
Cherry St. Historic Home - Blue Rm
SUPERHOSTPrivate room
Cherry St. Historic Home - Blue Rm
Price:€31 / night
Cozy cottage on small intown farm.
SUPERHOSTEntire guest house
Cozy cottage on small intown farm.
Price:€111 / night
Hilltown Cabin Hideaway: A River Runs Through It!
SUPERHOSTEntire cabin
Hilltown Cabin Hideaway: A River Runs Through It!
Price:€164 / night
Cozy Private Tiny House Trailer
SUPERHOSTCampervan/Motorhome
Cozy Private Tiny House Trailer
Price:€40 / night
Rent a cottage
Entire cottage
Rent a cottage
Price:€76 / night
E. Slate Carriage House
SUPERHOSTBarn
E. Slate Carriage House
Price:€108 / night
Sunny, light filled loft in 1873 Colonial
SUPERHOSTEntire flat
Sunny, light filled loft in 1873 Colonial
Price:€88 / night
Blue House Farm and Gardens
SUPERHOSTEntire flat
Blue House Farm and Gardens
Price:€133 / night
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