Chester Vacation Rentals

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Our top choices for Chester vacation rentals

9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
$263 nightly
The price is $266
Jan 20 - Jan 21, 2026
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
$164 nightly
The price is $166
Jan 8 - Jan 9, 2026
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
$137 nightly
The price is $155
Jan 5 - Jan 6, 2026
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
$281 nightly
The price is $293
Dec 24 - Dec 25
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
3.0 star property
$213 nightly
The price is $238
Jan 11 - Jan 12, 2026
Total with taxes and fees
Forava Cabins - Tiny Cabin in the Woods
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$366 nightly
The price is $371
Dec 24 - Dec 25
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (46)
"Great location, so clean and comfortable. "
United States
Barbara
$216 nightly
The price is $249
Jan 7 - Jan 8, 2026
Total with taxes and fees
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
9.6 out of 10, Exceptional, (41)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
$229 nightly
The price is $259
Dec 29 - Dec 30
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
$256 nightly
The price is $290
Jan 1 - Jan 2, 2026
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$236 nightly
The price is $279
Dec 28 - Dec 29
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (23)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$505 nightly
The price is $557
Dec 26 - Dec 27
Total with taxes and fees
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
9.4 out of 10, Exceptional, (6)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
United States
Jonathan O.
$220 nightly
The price is $249
Jan 20 - Jan 21, 2026
Total with taxes and fees
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
3.0 star property
$272 nightly
The price is $308
Dec 30 - Dec 31
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
10.0 out of 10, Exceptional, (72)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
$207 nightly
The price is $232
Dec 29 - Dec 30
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
$230 nightly
The price is $260
Jan 11 - Jan 12, 2026
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
10.0 out of 10, Exceptional, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
$236 nightly
The price is $279
Dec 28 - Dec 29
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1

Cottage in Middletown

Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$389 nightly
The price is $440
Dec 31 - Jan 1, 2026
Total with taxes and fees
Hello Small Stone

Vacation Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$331 nightly
The price is $376
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
$254 nightly
The price is $281
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
9.6 out of 10, Exceptional, (15)
"The property was amazing, Ceren was very accommodative, and we had a great time!"
United States
Mohit B.
$594 nightly
The price is $656
Dec 29 - Dec 30
Total with taxes and fees
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
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 $232 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 kitchenware, 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, Museum Village and Goosepond Mountain State Park 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.