Search Chester Cottages
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chester cottages
Terrific 3-bedroom cottage with AC in charming Cavendish
Terrific 3-bedroom cottage with AC in charming CavendishCavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
Mark G.
$536 nightly
The price is $600
Jul 1 - Jul 2
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to BrattleboroWalpole
9.6 out of 10, Exceptional, (9 reviews)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
Frances D.
$266 nightly
The price is $289
Jul 1 - Jul 2
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Ludlow Cabin on Lake Pauline w/ Outdoor Fire PitLudlow
$406 nightly
The price is $447
Jul 1 - Jul 2
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Spectacular Cottage with Swimming Pool and Foosball in Stratton, VermontStratton
$440 nightly
The price is $497
Jul 1 - Jul 2
Total with taxes and fees
$594 nightly
The price is $653
Jul 1 - Jul 2
Total with taxes and fees
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Luxe Mountain Home w/ Chefs Kitchen & Okemo ViewsLudlow
$1,679 nightly
The price is $1,847
Jul 1 - Jul 2
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find vacation rentals that suit your style
Cabins
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
Find out more about Chester
Chester Cottages information
Number of reviews | 11 |
|---|---|
Accommodation | 177 Cottages |
Lowest Price | $289 |
Highest Price | $1,847 |
Frequently asked questions
Explore a world of travel with Expedia
- Condo Resorts in Baltimore
- Cabin Rentals in Andover
- Hotels with Hot Tubs in Springfield
- Cabin Rentals in Springfield
- B&B in Weston
- Resorts & Hotels with Spas in North Springfield
- Springfield Hotels
- B&B in Chester
- Woodstock Hotels
- Pet-Friendly Hotels in Springfield
- Weston Hotels
- Cheap Hotels in Springfield
- Rockingham Hotels
- Cabin Rentals in Grafton
- Killington Hotels
- Brattleboro Hotels
- Cabin Rentals in Ludlow
- Condo Rentals in Proctorsville
- Cabin Rentals in Weston
- Chester Hotels
- Ludlow Hotels
- B&B in North Springfield
- Motels in Windham
- Hotels near Okemo Mountain Resort
- B&B in Andover
- B&B in Baltimore
- Rutland Hotels
- Ski Hotels in Chester
- 5 Star Hotels in North Springfield
- North Springfield Hotels
- Romantic Hotels in Grafton
- B&B in Proctorsville
- Grafton Hotels
- Motels in Chester
- Guest Houses in Saxtons River
- Hotels near Vermont Country Store
- Hotels with Free Breakfast in Grafton
- Cabin Rentals in Chester
- Cabin Rentals in North Springfield
- Stratton Hotels
- Motels in North Springfield
- Hotels near Mount Snow
- Resorts & Hotels with Spas in Springfield
- Cottages in Grafton
- Londonderry Hotels
- Adults Only Resorts & in Chester
- B&B in Athens
- Rv Parks in Grafton
- Chester Depot Hotels
- Cabin Rentals in Proctorsville
- Luxury Hotels in Chester
- Luxury Hotels in Grafton
- Apartments in Springfield
- Best Western Hotels in Springfield
- Resorts in Athens
- Pet-Friendly Hotels in Grafton
- Andover Hotels
- Cottages in Athens
- Pet-Friendly Hotels in Chester
- Manchester Hotels
- B&B in Springfield
- Motels in Springfield
- Condo Rentals in Saxtons River
- Gay friendly Hotels in Chester
- B&B in Ludlow
- Hotels near Magic Mountain Ski Resort