Chester Vacation Rentals

Compare 5 vacation rentals.
USA > Vermont > Chester

Make Chester your next getaway

Chester

Explore Chester house rentals, and more

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House rentals

View 5 House rentals

Explore more vacation rental amenities in Chester

Pool | Lake view | Lakefront | Riverfront | Ski-in/ski-out | Water view | Waterfront | A/C | Fireplace | Washer/dryer

Chester vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Okemo Valley Chalet
5 Bed | 2.5 Bath | Sleeps 13

Okemo Valley Chalet - Chester, VT

$516 avg / night
4.88 (8)
Mont House
4 Bed | 3.5 Bath | Sleeps 8

Mont House - Chester, VT

$629 avg / night
5.0 (4)
House At Dream Barn Hollow
2 Bed | 2 Bath | Sleeps 6

House At Dream Barn Hollow - Chester, VT

$303 avg / night
Country Riverside Retreat
2 Bed | 2 Bath | Sleeps 6

Country Riverside Retreat - Chester, VT

$317 avg / night
5.0 (2)
Town & Mountain
3 Bed | 2 Bath | Sleeps 7

Town & Mountain - Chester, VT

$430 avg / night
5.0 (1)

View 0 more homes

Recent Chester vacation rental reviews

Beautiful house and back yard. Very spacious and clean.
Max H. | Oct 2024
Home was larger than it appears in the add. Beautiful , very comfortable beds. Everything you needed was there. Will definitely book this place again
mark d. | Oct 2024
Our whole family (two adults, two teens, and a dog) enjoyed this large and clean property. Good location.
Pamela M. | Oct 2024
Chester Frequently Asked Questions

Yes, 24 of our Chester homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 148 of our Chester vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Chester vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Chester team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Chester, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

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