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Vacation rentals in Chester

Vacation rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

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

  • 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.”

  • View of Green, easy access to town
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1.5 shared bathrooms
    View of Green, easy access to town

    This is the second bedroom available in our home. It is a sweet, simple room, with views to the green which is our backyard, leading to the Mill River. Our house is small and cozy. Your room is private, but we share bathrooms, kitchen and livingroom.

    What guests are saying:

    “It was just like staying with a friend. Lani is an excellent host. She was waiting for us when we arrived and took the time to show us around her characterful house and our room. The bedroom and bathroom were incredibly clean and tidy and we had access to all the amenities that we could have possibly needed. We had a restful night’s sleep as the bed and pillows were comfortable and the house is located in a peaceful setting right by a river. We would love to return!”

  • Spacious Duplex in Heart of the Berkshires
    SUPERHOSTEntire house · 4 guests · 2 beds · 1.5 bathrooms
    Spacious Duplex in Heart of the Berkshires

    Equidistant to MASS MoCA, Tanglewood, Clark Art Institute, Jacob's Pillow, Jiminy Peak, and more, and walking distance to downtown Pittsfield. Spacious, two-floor duplex in the heart of the Berkshires.

    What guests are saying:

    “We had a great time in Jonathan's and Abby's place in Pittsfield. The duplex is very clean and nicely furnished. The kitchen is very well stocked with about everything you would need to cook meals just as you would at home. We enjoyed the proximity to lots of nature spots nearby, namely Cheshire Cobbles and Wahconah Falls.”

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Chester holiday rentals

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

Other great holiday rentals in Chester

BERKSHIRE COTTAGE BY CRYSTAL CLEAR LAKE
SUPERHOSTEntire cottage
BERKSHIRE COTTAGE BY CRYSTAL CLEAR LAKE
Price:€152 / night
The Northridge enclosed gazebo
SUPERHOSTHut
The Northridge enclosed gazebo
Price:€84 / night
Comfortable private suite in 1850's farmhouse
SUPERHOSTPrivate room
Comfortable private suite in 1850's farmhouse
Price:€53 / night
The Old Parish Hall, right in down town!
SUPERHOSTEntire flat
The Old Parish Hall, right in down town!
Price:€90 / night
Studio apartment the Rodeo Room
SUPERHOSTEntire guest suite
Studio apartment the Rodeo Room
Price:€62 / night
Just Be Cabin
SUPERHOSTEntire cabin
Just Be Cabin
Price:€44 / night
Goreytastic Private ApARTment @ the EMC
SUPERHOSTEntire guest suite
Goreytastic Private ApARTment @ the EMC
Price:€71 / night
One private single room in Lenox
Private room
One private single room in Lenox
Price:€44 / night
Modern, Spacious Master Bedroom and Bathroom
SUPERHOSTPrivate room
Modern, Spacious Master Bedroom and Bathroom
Price:€88 / night
Queen Room w/Private Bath in Quiet Berkshires Home
Private room
Queen Room w/Private Bath in Quiet Berkshires Home
Price:€58 / night
Happy Maples!
SUPERHOSTEntire guest suite
Happy Maples!
Price:€105 / night
Mi Casita Rm#1 (1 Queen Bed)
SUPERHOSTPrivate room
Mi Casita Rm#1 (1 Queen Bed)
Price:€69 / night
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