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Chester Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chester vacation rentals

A hot tub with a wooden deck and railing, surrounded by a grassy area and a stone wall.

1. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
10.0 out of 10, Exceptional, (2 reviews)
"5 star experience! We will definitely stay here again. The host was responsive, and the house was in perfect condition. The pool was clean. The sauna was spotless!"
United States
Benny P.
$2,529 nightly
The price is $2,943
Sep 27 - Sep 28
Total with taxes and fees
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

2. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
Hay Loft Apartment in Barn - Goshen
A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

3. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.4 out of 10, (18 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
$154 nightly
The price is $174
Oct 13 - Oct 14
Total with taxes and fees
Cottage Suites
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

4. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.6 out of 10, Excellent, (19 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
$137 nightly
The price is $155
Sep 28 - Sep 29
Total with taxes and fees
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

5. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$269 nightly
The price is $281
Sep 27 - Sep 28
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

6. 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, (47 reviews)
"In the area for my nephew’s graduation. Loved walking around Warwick and checking out shops.Beautiful accommodations. Very clean, easy check in, comfortable bed. Appreciated the options for coffee and tea. Overall, a great stay."
United States
Gwenda M.
$209 nightly
The price is $236
Sep 27 - Sep 28
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A hot tub in a lush garden with a stone wall and outdoor furniture.

7. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (67 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
$544 nightly
The price is $569
Sep 27 - Sep 28
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

8. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 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.
$187 nightly
The price is $221
Sep 29 - Sep 30
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A circular outdoor seating area with a fire pit, surrounded by a stone border, set in a lush green forest.

9. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
$824 nightly
The price is $862
Sep 27 - Sep 28
Total with taxes and fees
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

10. The Wine House

The Wine House
Warwick
10.0 out of 10, Exceptional, (38 reviews)
"Amazing place - we will definitely be back ."
United States
Robin
$246 nightly
The price is $278
Sep 27 - Sep 28
Total with taxes and fees
The Wine House
A spacious living room with a stone fireplace, two white sofas, a glass coffee table, and large windows.

11. Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (13 reviews)
"The breakfast was lovely!"
United States
Tara
$250 nightly
The price is $283
Oct 1 - Oct 2
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
A two-story house with a porch, a table, and chairs outside.

12. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
Historic Horse Barn Apartment in Goshen
A room with a chandelier, a sofa, a table, and a cabinet.

13. 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
8.8 out of 10, Excellent, (23 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
$144 nightly
The price is $163
Oct 7 - Oct 8
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
A dark blue door with a glass panel, flanked by two potted topiary trees, a welcome mat, and a wall-mounted light fixture.

14. Charming 2-bedroom apartment in the Village of Warwick

Charming 2-bedroom apartment in the Village of Warwick
Warwick
9.4 out of 10, Exceptional, (3 reviews)
"Clean, family friendly, close to everything."
United States
Milena P.
$270 nightly
The price is $305
Oct 1 - Oct 2
Total with taxes and fees
Charming 2-bedroom apartment in the Village of Warwick
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

15. Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (20 reviews)
"Great hosts and great location!"
United States
Shelby A.
$256 nightly
The price is $294
Sep 27 - Sep 28
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
A kitchen with white cabinets, stainless steel appliances, a microwave, oven, and a refrigerator.

16. Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
9.8 out of 10, Exceptional, (17 reviews)
"Very nice property in a nice neighborhood . Had all the amenities we needed and Ruth was super responsive. If we are in the area again, we will def stay at this location. "
United States
Kimberly R.
$594 nightly
The price is $702
Sep 28 - Sep 29
Total with taxes and fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (12 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$357 nightly
The price is $379
Sep 27 - Sep 28
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

18. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$285 nightly
The price is $290
Sep 27 - Sep 28
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A hot tub with a view of a lake and houses in the background.

19. Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
10.0 out of 10, Exceptional, (41 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
$436 nightly
The price is $493
Sep 29 - Sep 30
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

20. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (52 reviews)
"One of the cleanest VRBOs I ever stayed in - it smelled so good. Very cozy and had everything we needed. The location is great!"
United States
Tara K.
$212 nightly
The price is $240
Sep 28 - Sep 29
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
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

Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

8/10 Good
"Clean place and good breakfast"
Stacy 1-night trip
Posted 9 hours ago
Hilton Garden Inn Nanuet

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 $93 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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental near Chester is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chester?

Expedia has 11 vacation rentals for your stay in Chester.

What can I see and do in Chester?

Cultural attractions include Museum Village and Sugar Loaf Performing Arts Center, whereas The Rock Sports Complex is one spot to enjoy nature. While here, Castle Fun Center 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.