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Chester Vacation Rentals

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Our top choices for Chester vacation rentals

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (29 reviews)
"Clean and quiet."
United States
Ted
$182 nightly
The price is $185
Jul 13 - Jul 14
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
$170 nightly
The price is $201
Jul 13 - Jul 14
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
Vernon Township
10.0 out of 10, Exceptional, (62 reviews)
"Great time, comfortable stay! "
United States
Yuliya
$289 nightly
The price is $327
Aug 3 - Aug 4
Total with taxes and fees
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
$418 nightly
The price is $447
Jul 21 - Jul 22
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
$282 nightly
The price is $333
Jul 16 - Jul 17
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$239 nightly
The price is $263
Jul 29 - Jul 30
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
$262 nightly
The price is $296
Jul 13 - Jul 14
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.4 out of 10, Exceptional, (30 reviews)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
$194 nightly
The price is $218
Jul 12 - Jul 13
Total with taxes and fees
Cozy Loft Cabin high above Bashakill Wildlife Refuge

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
$208 nightly
The price is $235
Jul 13 - Jul 14
Total with taxes and fees
Historic Cabin with Pool & Fire Pit

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (17 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
$170 nightly
The price is $192
Jul 12 - Jul 13
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
$239 nightly
The price is $282
Jul 12 - Jul 13
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (86 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
$209 nightly
The price is $234
Aug 9 - Aug 10
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #225

Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #225
Vernon
9.8 out of 10, Exceptional, (10 reviews)
"Nice place!!"
United States
Lukasz
$279 nightly
The price is $314
Jul 30 - Jul 31
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #225

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$521 nightly
The price is $574
Jul 12 - Jul 13
Total with taxes and fees
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
$457 nightly
The price is $517
Jul 19 - Jul 20
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (71 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
$266 nightly
The price is $314
Jul 10 - Jul 11
Total with taxes and fees
Cozy country efficiency in the Hudson Valley

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (9 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$214 nightly
The price is $239
Jul 14 - Jul 15
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (41 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
$239 nightly
The price is $270
Jul 12 - Jul 13
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$436 nightly
The price is $486
Jul 14 - Jul 15
Total with taxes and fees
Fabulous 3bdrm Home w/parking!

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$283 nightly
The price is $295
Jul 12 - Jul 13
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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 $115 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.

Explore a world of travel with Expedia

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?

Lakefront Paradise Pool + Paddle Boats Sleeps 12: This vacation home rental near Chester offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Chester?

Expedia has 9 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. You’ll find favorite places to visit like LEGOLAND® New York and Woodbury Common Premium Outlets in the larger area.

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.