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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chester apartments

TV
Cozy 1-bedroom retreat minutes from West Point!

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)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is AED 343
AED 696 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroom retreat minutes from West Point!
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!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (15)
"Great Unit."
United States
Rudy R.
The price is AED 275
AED 947 total
includes taxes & fees
11 Jan - 12 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
3 bedrooms, desk, iron/ironing board, travel crib
Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (10)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is AED 312
AED 1,409 total
includes taxes & fees
11 Jan - 12 Jan
Local Artist Inspired | Walk to WestPoint + King Bed
Interior
Dream getaway apartment in the foot of Gunks Ridge

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)
"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
The price is AED 237
AED 632 total
includes taxes & fees
9 Feb - 10 Feb
Dream getaway apartment in the foot of Gunks Ridge
Apartment | 1 bedroom
Cozy Modern Studio Near Lake Porch Fire Pit

Cozy Modern Studio Near Lake Porch Fire Pit

Cozy Modern Studio Near Lake Porch Fire Pit
2.0 star property
Monroe
Cozy Modern Studio Near Lake Porch Fire Pit
Dining
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

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)
"Great time and great place to stay "
United States
S S.
The price is AED 404
AED 880 total
includes taxes & fees
27 Jan - 28 Jan
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Exterior detail
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Port Jervis
10.0 out of 10, Exceptional, (6)
"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.
The price is AED 361
AED 1,160 total
includes taxes & fees
12 Jan - 13 Jan
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Exterior detail
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is AED 404
AED 863 total
includes taxes & fees
20 Jan - 21 Jan
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Interior
Lux APT Your home away from home.

Lux APT Your home away from home.

Lux APT Your home away from home.
Beacon
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is AED 522
AED 1,001 total
includes taxes & fees
1 Feb - 2 Feb
Lux APT Your home away from home.
Interior
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

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

Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (42)
"We love staying in the apartment. Convenient to stores and restaurants. Ideal location. Have stayed before and look forward to staying again. "
United States
Cynthia W.
The price is AED 400
AED 910 total
includes taxes & fees
11 Jan - 12 Jan
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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)
"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 AED 629
AED 1,115 total
includes taxes & fees
9 Feb - 10 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
1 bedroom, desk, iron/ironing board, free WiFi
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Montgomery
10.0 out of 10, Exceptional, (3)
"Wonderful stay. Responded quickly to any issues even if it was a tiny one. Would absolutely stay here again. "
United States
Richard D.
The price is AED 545
AED 979 total
includes taxes & fees
11 Jan - 12 Jan
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
1 bedroom, desk, iron/ironing board, free WiFi
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.

Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.

Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Wurtsboro
9.0 out of 10, Wonderful, (2)
"The host was very welcoming and very responsive. The apartment was very cute and super clean. I came up for a Halloween event put on by a friend the location was very convenient in the downtown area and I could walk to most of the places I needed to get to I very much enjoyed my stay here and would stay again if I’m in the area. "
United States
Sheena C.
The price is AED 477
AED 1,003 total
includes taxes & fees
21 Jan - 22 Jan
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (66)
"Such a cute place to stay"
United States
Melissa
The price is AED 643
AED 1,202 total
includes taxes & fees
12 Jan - 13 Jan
Cozy country efficiency in the Hudson Valley
Apartment | 1 bedroom
Bright Studio Retreat w Deck Nature Views

Bright Studio Retreat w Deck Nature Views

Bright Studio Retreat w Deck Nature Views
2.0 star property
Monroe
Bright Studio Retreat w Deck Nature Views
Property grounds
Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is AED 577
AED 968 total
includes taxes & fees
10 Jan - 11 Jan
Villa Verde B&B, Greenwood Lake NY, 1
Dining
Hudson Valley Top Getaway with a River View B

Hudson Valley Top Getaway with a River View B

Hudson Valley Top Getaway with a River View B
2.0 star property
Newburgh
The price is AED 602
AED 1,171 total
includes taxes & fees
10 Jan - 11 Jan
Hudson Valley Top Getaway with a River View B
Outdoor dining
The Appalachian at Mountain Creek

The Appalachian at Mountain Creek

The Appalachian at Mountain Creek
Vernon Township
The price is AED 430
AED 886 total
includes taxes & fees
28 Jan - 29 Jan
The Appalachian at Mountain Creek
Fridge, microwave, oven, stovetop
The Wine House, Sitting atop of Warwick's brand new Wine Bar

The Wine House, Sitting atop of Warwick's brand new Wine Bar

The Wine House, Sitting atop of Warwick's brand new Wine Bar
Warwick
10.0 out of 10, Exceptional, (26)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is AED 645
AED 941 total
includes taxes & fees
11 Jan - 12 Jan
The Wine House, Sitting atop of Warwick's brand new Wine Bar
TV
Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (21)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
The price is AED 767
AED 1,299 total
includes taxes & fees
9 Feb - 10 Feb
Walk to WP Gate + Free Parking!
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"The service was great as we had to change rooms and they accommodated our request. Given a quieter room we slept with peace. The service at the restaurant was under par but dinner was good otherwise "
Ellen 1-night trip
Posted 3 days ago
Overlook Lodge at Bear Mountain

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find 18 accommodations in Chester. Though there aren't many apartments, we can help you locate similar accommodations. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. Even filter by similar property types like vacation homes, condos, or guest houses. You might want to visit the area's shops and enjoy its restaurants.
How do you know if an apartment is the best choice for you?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, but also for families who want the conveniences of home.
What's a favorite apartment I should consider for a stay in Chester?
Listed below are some of the favorite apartments in the area: Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!: Located in Wallkill, 17.9 mi/28.7 km from the heart of Chester. Includes free WiFi, private balconies, and Smart TVs. Access to onsite laundry facilities is available on site. Modern penthouse suite in a restored grain tower with private roof deck.: Located 8.8 mi/14.1 km away in Warwick. Free WiFi and Smart TVs are included. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer: Located in Beacon, 18.3 mi/29.5 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA: Located 17.8 mi/28.7 km away in Beacon. Amenities include private patios. Access to onsite laundry facilities is available on site. Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer: Located in Beacon, 18.3 mi/29.5 km from Chester. Includes Smart TVs. Access to onsite laundry facilities is available on site.
What will the weather be like in Chester?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Chester. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What should I see and do in Chester?
Chester is known for its restaurants and shops. 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's the best way to get to and around Chester?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Stewart Intl. Airport (SWF), which is located 13.5 mi (21.7 km) away from the city center. Otherwise, look for flights into Caldwell, NJ (CDW-Essex County), which is 33.6 mi (54.1 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.