Vacation Homes in Chester, VT
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Top Vacation Homes in Chester

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

The Dorothy-10 minutes from Okemo- freshly renovated

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Riverside Getaway! Minutes to Downtown Woodstock

Shuttle or walk to village and lifts! Hot Tub + More!

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

Angel Bear Chalet- Private Lake/Beach/Sauna/Hot Tub/Gym/Firepit/Float Trampoline

Family Friendly Hilltop House In Putney Vermont

Beautiful Waterfront , four season home on charming Crescent Lake!

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Cozy cottage tucked away in the woods
Top hotels in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Find the Best Vacation Homes in Chester
Why book a vacation home in Chester?
Vacation homes in Chester make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Chester?
Private Chester rental homes range between $118 - $538 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Chester vacation home rentals. You might look for Chester rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Chester offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Chester?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chester. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chester hotels and vacation homes that best suit your stay. We also have deals for flights, and Chester car rentals. You’ll save even more when you bundle your items into a Chester vacation package!
How many vacation homes are available to book in Chester?
There are 1006 rental homes in Chester. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Chester?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Chester Vacation Homes essential information
Accommodation | 1006 Vacation Homes |
|---|---|
Lowest Price | $118 |
Highest Price | $538 |
Popular accommodation | PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC., The Dorothy-10 minutes from Okemo- freshly renovated, Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, Riverside Getaway! Minutes to Downtown Woodstock, Shuttle or walk to village and lifts! Hot Tub + More!, By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing., Angel Bear Chalet- Private Lake/Beach/Sauna/Hot Tub/Gym/Firepit/Float Trampoline, Family Friendly Hilltop House In Putney Vermont, Beautiful Waterfront , four season home on charming Crescent Lake!, Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town, Cozy cottage tucked away in the woods, West Dover Home - 3 Miles to Mount Snow Resort! |






