Chester Vacation Rentals

Compare 5 vacation rentals.
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Make Chester your next getaway

Chester

Top Chester property types

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House rentals

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Popular amenities for Chester vacation rentals

Popular
Dog-friendly Internet Electric vehicle charger
Kingdom Valley Farmhouse
3 Bedroom | 1.5 Bath | Sleeps 6

Kingdom Valley Farmhouse - Chester, VT

$221 avg / night
(excludes fees and taxes)
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
2 Bedroom | 1 Bath | Sleeps 4

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes! - Chester, VT

$158 avg / night
(excludes fees and taxes)
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
3 Bedroom | 1 Bath | Sleeps 6

Hike, Ski & Unwind: Cabin w/ Deck in Chester! - Chester, VT

$162 avg / night
(excludes fees and taxes)
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
5 Bedroom | 2 Bath | Sleeps 10

Chester Farmhouse on 100 Acres, 15 Min to Okemo! - Chester, VT

$271 avg / night
(excludes fees and taxes)
5.0 (5)
Private Chester Home w/ Deck, Mins to Skiing!
3 Bedroom | 3 Bath | Sleeps 8

Private Chester Home w/ Deck, Mins to Skiing! - Chester, VT

$377 avg / night
(excludes fees and taxes)
4.67 (3)

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Browse more vacation rental amenities in Chester

Lake view | Water view | Waterfront | A/C | Fireplace | Washer/dryer | Balcony | Bikes | Golf on-site | Ping-pong table

Recent Chester guest reviews

A wonderful stay at a great house. Plenty to keep the kids busy and very comfortable. A quick drive to Okemo. We will be back.
Joseph . | Feb 2024
My family (4x) stayed at this home over the MLK weekend. Great place that exceeded our expectations. Certainly room for a few more but we loved it. Very well thought out home and interior design. Kitchen was well stocked, linens were nice and we look forward to coming back.
Joe . | Jan 2024
The house was easy to get to. A quick 10 minute ride to and from the slopes. The house was clean, modern and well stocked. We will definitely stay there again in the future.
William . | Jan 2023
Chester vacation rental FAQ

Yes. 151 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Chester, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

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