Chester Cottage Rentals

Compare Cottages, Resorts, & Rentals in Chester, Connecticut, USA

See More Properties

About Chester Vacation Rentals

There are over 60 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 1111.1 ft², with prices averaging US $505 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, CT


Chester Creek Marina 66 Properties
Chester Center 60 Properties
Norma Terris Theater 57 Properties

Frequently Asked Questions About Chester?

What are the top cottages, summer homes, and lake houses in Chester?

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 60 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 (2)

NeighborhoodProperty Count
Deep River Center Rental Cottages and Private Getaways in Old Saybrook, Connecticut 65
Chester Center Rental Cottages and Private Getaways in Old Saybrook, Connecticut 60

There are 3 Vacation Cottages in Chester and 45 rentals

Recently Booked Hotels, Resorts, or Rentals in Chester