Chester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Chester vacation rentals

Deluxe Cabin, Garden View | Free WiFi

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
The price is ￥39,660
￥44,271 total
includes taxes & fees
Feb 24 - Feb 25
Forava Cabins - Tiny Cabin in the Woods
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
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.
The price is ￥14,311
￥28,861 total
includes taxes & fees
Feb 4 - Feb 5
Cozy 1-bedroom retreat minutes from West Point!
Terrace/patio

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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥13,271
￥51,906 total
includes taxes & fees
Feb 1 - Feb 2
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior

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, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
The price is ￥8,331
￥24,778 total
includes taxes & fees
Feb 1 - Feb 2
Dream getaway apartment in the foot of Gunks Ridge
Fridge, oven, stovetop, coffee/tea maker

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is ￥11,486
￥39,482 total
includes taxes & fees
Feb 1 - Feb 2
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Interior

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
9.2 out of 10, Wonderful, (9 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.
The price is ￥13,920
￥24,066 total
includes taxes & fees
Feb 9 - Feb 10
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥46,325
￥70,262 total
includes taxes & fees
Feb 2 - Feb 3
Rustic Cabin in Fishkill!
Outdoor spa tub

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (60 reviews)
"This cottage was perfect for our stay. We have family nearby and this was the perfect retreat after busy days. We will be booking again. The space is clean and welcoming the land is beautiful! "
United States
Heather A.
The price is ￥37,902
￥76,207 total
includes taxes & fees
Feb 1 - Feb 2
Country House w/Hot Tub, Deck, Grill & Fire Pit
Dining

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is ￥17,764
￥38,433 total
includes taxes & fees
Feb 1 - Feb 2
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Interior

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
The price is ￥23,949
￥42,968 total
includes taxes & fees
Mar 1 - Mar 2
Villa Verde B&B, bsm, Greenwood Lake NY
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
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.
The price is ￥28,139
￥53,528 total
includes taxes & fees
Feb 4 - Feb 5
Lovely 3BR Home with parking-Walk to WP Gate!
Fridge, microwave, oven, stovetop

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
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.
The price is ￥23,959
￥43,226 total
includes taxes & fees
Feb 4 - Feb 5
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥34,457
￥63,932 total
includes taxes & fees
Jan 30 - Jan 31
Contemporary Cozy Cottage
Outdoor dining

Creekfront Cabin Sauna & Hot Tub Hikers Hollow

Creekfront Cabin Sauna & Hot Tub Hikers Hollow
Cuddebackville
10.0 out of 10, Exceptional, (5 reviews)
"Definitely recommend to anyone looking to get away from the busyness for a while! It's a beautiful home away from home!"
United States
Aaron B.
The price is ￥38,418
￥85,538 total
includes taxes & fees
Feb 2 - Feb 3
Creekfront Cabin Sauna & Hot Tub Hikers Hollow
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.4 out of 10, Exceptional, (57 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is ￥37,902
￥48,421 total
includes taxes & fees
Jan 31 - Feb 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior

Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (27 reviews)
"The property was amazing and Kimberly was the greatest host! Can’t wait to visit again!"
United States
Logan W.
The price is ￥51,482
￥81,365 total
includes taxes & fees
Feb 7 - Feb 8
Modern penthouse suite in a restored grain tower with private roof deck.
Dining

Serene Rustic Retreat with Lake

Serene Rustic Retreat with Lake
Cuddebackville
10.0 out of 10, Exceptional, (8 reviews)
"Amazing stay and beautiful home!"
United States
Koby A.
The price is ￥30,628
￥73,674 total
includes taxes & fees
Jan 30 - Jan 31
Serene Rustic Retreat with Lake
Smart TV

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)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is ￥22,741
￥44,804 total
includes taxes & fees
Jan 31 - Feb 1
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Apartment | 1 bedroom

Rustic Lakefront Studio w Deck Workspace

Rustic Lakefront Studio w Deck Workspace
2.0 star property
Monroe
Rustic Lakefront Studio w Deck Workspace
Terrace/patio

Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room

Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room
West Milford
10.0 out of 10, Exceptional, (4 reviews)
"The property was spotless, comfortable, and had everything we needed. The location was perfect—close to attractions yet quiet and relaxing. The hosts were amazing, welcoming and very responsive, they were welling to help us at all times and they may made sure the whole experience was smooth and enjoyable. We’d definitely stay here again!"
United States
Bana S.
The price is ￥41,957
￥86,090 total
includes taxes & fees
Feb 1 - Feb 2
Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Room is clean and spacious. Staff are extremely friendly and helpful. Breakfast is good."
Yeng ping 2-night trip
Posted 3 days ago
Hampton Inn Harriman Woodbury

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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 11 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.