Chester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Our top choices for Chester vacation rentals

9.6 out of 10, Exceptional, (24 reviews)
"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
$163 nightly
The price is $166
Feb 3 - Feb 4
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$175 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
3.0 star property
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
$226 nightly
The price is $253
Jan 21 - Jan 22
Total with taxes and fees
Forava Cabins - Tiny Cabin in the Woods
10.0 out of 10, Exceptional, (3 reviews)
"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.
$376 nightly
The price is $382
Jan 14 - Jan 15
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !
9.8 out of 10, Exceptional, (15 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Jan 15 - Jan 16
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.4 out of 10, Exceptional, (8 reviews)
"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.
$134 nightly
The price is $151
Feb 2 - Feb 3
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
2.0 star property
9.0 out of 10, Wonderful, (12 reviews)
"Great location!"
United States
Alozie E.
$438 nightly
The price is $438
Jan 14 - Jan 15
Total with taxes and fees
Stylish & Peaceful Getaway on 3 Private Acres
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
$207 nightly
The price is $238
Jan 19 - Jan 20
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
2.0 star property
$210 nightly
The price is $238
Jan 14 - Jan 15
Total with taxes and fees
Natural Getaway at Orchard Farm Lakeside Retreat
9.4 out of 10, Exceptional, (54 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
$282 nightly
The price is $318
Jan 16 - Jan 17
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
10.0 out of 10, Exceptional, (59 reviews)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
$477 nightly
The price is $498
Jan 14 - Jan 15
Total with taxes and fees
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Cabin in Cuddebackville

Serene Rustic Retreat with Lake
2.0 star property
10.0 out of 10, Exceptional, (8 reviews)
"Amazing stay and beautiful home!"
United States
Koby A.
$474 nightly
The price is $481
Jan 14 - Jan 15
Total with taxes and fees
Serene Rustic Retreat with Lake
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
$256 nightly
The price is $303
Jan 15 - Jan 16
Total with taxes and fees
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$432 nightly
The price is $476
Jan 14 - Jan 15
Total with taxes and fees
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay!"
United States
Lisi M.
$472 nightly
The price is $533
Jan 16 - Jan 17
Total with taxes and fees
Modern penthouse suite in a restored grain tower with private roof deck.
2.0 star property
8.8 out of 10, Excellent, (3 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Jan 19 - Jan 20
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Vacation Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7 reviews)
"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.
$255 nightly
The price is $285
Jan 14 - Jan 15
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (5 reviews)
"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.
$272 nightly
The price is $301
Feb 9 - Feb 10
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
2.0 star property
$272 nightly
The price is $307
Jan 14 - Jan 15
Total with taxes and fees
Bright Studio Retreat w Deck Nature Views

Vacation Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
$367 nightly
The price is $420
Jan 14 - Jan 15
Total with taxes and fees
Contemporary Cozy Cottage
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.
Save an average of 15% on thousands of hotels when you're signed in

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 $246 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.