Chester Vacation Rentals, Hotels, & Places to Stay
About Chester Vacation Rentals
There are more than 93 places to stay that are available in Chester. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Chester.
Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in Chester, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Chester. Places to stay near Chester are 1156.78 ft² on average, with prices averaging US $367 a night.
Varoom helps you discover places to stay and suggests things to do to create great travel memories in Chester. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Top Rental Accommodation Types in Chester
| Type | Count |
|---|---|
| Vacation Homes | 58 |
| Holiday Apartments | 5 |
Use these Quick Filters to Find a Vacation Rental in Chester
★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Chester today.
Weather in Chester, VT
View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.
Top Attractions Around Chester, VT
Varoom offers a large selection of top attractions around Chester . Research things to do on your vacation before you visit Chester.
Other Places to Stay in Chester, VT
Frequently Asked Questions About Chester?
What are the top vacation rentals in Chester?
We have scoured the web to find you options in Chester. If you plan on staying near or in the Chester area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay in Chester:
- Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required
- Circa 1868 Chester Home/Victorian Farmhouse-Less than 20 MIN TO OKEMO
- Vermont Charm in the 1840 Gideon Lee House
- Log cabin near Okemo/Ludlow on 25 acres borders state forest w/trails nearby
- Cheerful residential home with lots of space
- Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
- Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
- Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Which vacation homes in Chester are best for families?
If you are looking for a place to stay that is family-friendly in Chester, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Chester:
How many Varoom vacation rentals are available in Chester?
Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2026 is over 93 in the Chester area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Chester.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Chester Depot Vacation Rentals in Chester, Vermont | 58 |
