Compare Cottages, Resorts, & Rentals in Chester, Vermont, USA
About Chester Vacation Rentals
There are over 94 amazing vacation rentals available in Chester. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Chester.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Chester, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Chester. The average size of places to stay near Chester is approximately 1147.45 ft², with prices averaging US $367 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Chester. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Chester, VT
Frequently Asked Questions About Chester?
What are the top cottages, summer homes, and lake houses 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
How many rentals, hotels, or resorts are available in Chester?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 94 properties listed by Vacation Cottage in the Chester area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Chester.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Chester Depot Rental Cottages and Private Getaways in Chester, Vermont | 58 |
