Chester Vacation Rentals

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Our top choices for Chester vacation rentals

Forava Cabins - Tiny Cabin in the Woods

Forava Cabins - Tiny Cabin in the Woods
3.0 star property
Ringwood
10.0 out of 10, Exceptional, (1 review)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
$231 nightly
The price is $258
Jan 22 - Jan 23
Total with taxes and fees
Forava Cabins - Tiny Cabin in the Woods

Bright Studio Retreat w Deck Nature Views

Bright Studio Retreat w Deck Nature Views
2.0 star property
Monroe
$278 nightly
The price is $314
Jan 11 - Jan 12
Total with taxes and fees
Bright Studio Retreat w Deck Nature Views

Natural Getaway at Orchard Farm Lakeside Retreat

Natural Getaway at Orchard Farm Lakeside Retreat
2.0 star property
Monroe
$210 nightly
The price is $238
Jan 11 - Jan 12
Total with taxes and fees
Natural Getaway at Orchard Farm Lakeside Retreat

NEW 5 Trinity Pl Cornwall NY 12518

NEW 5 Trinity Pl Cornwall NY 12518
2.0 star property
Cornwall
$765 nightly
The price is $904
Jan 12 - Jan 13
Total with taxes and fees
NEW 5 Trinity Pl Cornwall NY 12518

Rustic Lakefront Studio w Deck Workspace

Rustic Lakefront Studio w Deck Workspace
2.0 star property
Monroe
$210 nightly
The price is $238
Jan 11 - Jan 12
Total with taxes and fees
Rustic Lakefront Studio w Deck Workspace

Hidden Lakefront Gem on a Gated Countryside Escape

Hidden Lakefront Gem on a Gated Countryside Escape
2.0 star property
Monroe
$210 nightly
The price is $238
Jan 11 - Jan 12
Total with taxes and fees
Hidden Lakefront Gem on a Gated Countryside Escape
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

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $151 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Chester?

Yes, you can find vacation rentals in Chester close to Castle Fun Center, or you can go with a more remote option if you'd like a relaxing place to stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffeehouses during your trip.

What are some of the best vacation home rentals in Chester?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Chester offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Chester?

Expedia has 10 vacation rentals for your stay in Chester.

What can I see and do in Chester?

Family-friendly attractions include Castle Fun Center, whereas The Rock Sports Complex is a spot to enjoy the outdoors. While here, Goosepond Mountain State Park and Museum Village are other places worth a visit.

What are vacation rentals like in Chester?

Vacation rentals are privately owned properties you can reserve for several days or more in Chester. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.