Chester Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Chester vacation rentals

House (3 Bedrooms) | Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveler
The price is ₩281,586
₩868,411 total
includes taxes & fees
Dec 28 - Dec 29
Wilmington Retreat Near Trails, Skiing & Festivals
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very Good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is ₩584,832
₩726,948 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Long Trail House at Stratton Mountain Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"The staff was absolutely lovely. The Inn has a complimentary wine and cheese spread from 1730-1830. The hotel staff is on hand and its a great way to get to know fellow travelers and the staff themselves. My friend and I went both nights we were there and talked with Dave, one of the owners and the second night we spoke with Shawn (spelling?) We talked of books and going to Connecticut, to Yale and Mystic for Pizza. "
Nicole 2-night trip
Posted 2 days ago
The Jackson

Find out more about Chester

Search for Vacation rentals in Chester on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Chester using one of the methods below:

  • View our selection of featured Vacation rentals in Chester
  • Use the map to find apartments and other Vacation homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals in Chester near Bonnie's Bundles Dolls, or you can select a more remote option if you want a relaxing stay. The ski slopes and shops are just a few reasons why tourists like Chester. While you're in the area, grab a bite or have a drink at the coffeehouses and restaurants.

How many vacation rentals will I find in Chester?

Choose from 34 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Bonnie's Bundles Dolls and DaVallia Art & Accents are a couple of family-friendly sights. Stratton Mountain Resort and Vermont Country Store are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.