Skip to content
Some info has been automatically translated. Show original language

Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester

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

Cabin in Chester
HavenHaus: Cozy A-Frame Cabin
Escape to the mountains with this charming A-frame home in Western MA. Perfect for a family or group of 4-6, this cozy retreat offers scenic views and all the amenities you need for a relaxing getaway. With 2 lofted beds, an open-concept living area, and a full kitchen, you'll have everything you need to feel right at home. Enjoy a cup of coffee on the deck, surrounded by nature, or curl up by the fireplace with a good book. Book your stay today and experience the beauty of the Berkshires!
$149 per night
Home in Chester
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!
$140 per night
Rental unit in Chester
Quiet getaway in the Berkshires
Very nice quite place Two floors must climb stairs 3 bedrooms very large master Fully equipped kitchen Two full baths and laundry area Deck off the kitchen with fire pit in the back yard Lots of hiking and skiing in and around the area or stay and relax Carm’s diner for a great Breakfast Chester Common Table for dinner or The Blue Note Cafe for Pizza and a drink or Call for some takeout and a convenient store for anything you forgot
$98 per night

Stay near Chester's top sights

Photo of Chester Common Table
Chester Common Table11 locals recommend
Photo of Carm’s Restaurant and Coffee Shop
Carm’s Restaurant and Coffee Shop5 locals recommend
Photo of Classic Pizza
Classic Pizza8 locals recommend

Other great vacation rentals in Chester

Private room in Huntington
Ancient Colony
$55 per night
Home in Chester
Halloween Decorated Turn of Century Family Home
$95 per night
Home in Becket
Nerd Preservation Sanctuary
$97 per night
Rental unit in Easthampton
Private Farm Apartment, Close to Everything - 1BR
$82 per night
Cottage in Becket
Cozy lakeside cottage
$132 per night
Cottage in Becket
$179 per night
Home in Easthampton
Private Home~Old World Charm, Modern Conveniences
$126 per night
Home in Otis
Berkshire Skiing, snowmobiling, and winter fun!
$134 per night
Cottage in Becket
Staycation: Private Lake Cottage in Becket
$130 per night
Rental unit in Northampton
Bike Path Hideaway Near Smith, Cooley, Northampton
$112 per night
Cabin in Becket
Cabin with spectacular views of Robin Hood Lake
$185 per night
Guesthouse in Northampton
Mill River Cottage (pet friendly!)
$105 per night
  1. Airbnb
  2. United States
  3. Massachusetts
  4. Hampden County
  5. Chester