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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Chester apartments

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 €163
includes taxes & fees
10 Feb - 11 Feb
Cozy 1-bedroom retreat minutes from West Point!
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (47 reviews)
"Great place!"
United States
Sara B.
The price is €207
includes taxes & fees
10 Feb - 11 Feb
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
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 €148
includes taxes & fees
19 Feb - 20 Feb
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 €255
includes taxes & fees
18 Feb - 19 Feb
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
3 bedrooms, desk, iron/ironing board, travel cot

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (11 reviews)
"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.
Local Artist Inspired | Walk to WestPoint + King Bed
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 €238
includes taxes & fees
10 Feb - 11 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Apartment

Studio Lakeside Retreat Fast Wifi Great WFH

Studio Lakeside Retreat Fast Wifi Great WFH
2.0 star property
Monroe
The price is €182
includes taxes & fees
10 Feb - 11 Feb
Studio Lakeside Retreat Fast Wifi Great WFH
Desk, WiFi, bed sheets

Rustic Lakefront Studio w/ Deck + Workspace

Rustic Lakefront Studio w/ Deck + Workspace
Monroe
The price is €169
includes taxes & fees
10 Feb - 11 Feb
Rustic Lakefront Studio w/ Deck + Workspace
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!
Warwick
10.0 out of 10, Exceptional, (42 reviews)
"This loft is great! Well appointed with everything you need. "
United States
Jean L.
The price is €213
includes taxes & fees
10 Feb - 11 Feb
Luxe Loft on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
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
Beacon
9.8 out of 10, Exceptional, (43 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is €204
includes taxes & fees
17 Feb - 18 Feb
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
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.
Wurtsboro
9.0 out of 10, Wonderful, (2 reviews)
"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.
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
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
Port Jervis
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.
The price is €283
includes taxes & fees
10 Mar - 11 Mar
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Apartment (0 Bedroom) | Interior

Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
3.0 star property
Westbrookville
The price is €202
includes taxes & fees
28 Feb - 1 Mar
Close to Trails: Studio w/ Water Views
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (21 reviews)
"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
Walk to WP Gate + Free Parking!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (66 reviews)
"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."
United States
Lou F.
Cozy country efficiency in the Hudson Valley
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.
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay. Responded quickly to any issues even if it was a tiny one. Would absolutely stay here again. "
United States
Richard D.
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Apartment

Boutique King Suite at Orchard Lake Private Farm

Boutique King Suite at Orchard Lake Private Farm
2.0 star property
Monroe
The price is €232
includes taxes & fees
10 Feb - 11 Feb
Boutique King Suite at Orchard Lake Private Farm
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
Warwick
10.0 out of 10, Exceptional, (26 reviews)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is €222
includes taxes & fees
21 Feb - 22 Feb
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Property grounds

Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is €229
includes taxes & fees
10 Feb - 11 Feb
Villa Verde B&B, Greenwood Lake NY, 1
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 €455
includes taxes & fees
21 Feb - 22 Feb
Modern penthouse suite in a restored grain tower with private roof deck.
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"Nice hotel. Great staff. "
Ian 7-night trip
Posted 2 days ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about Chester

Chester Apartments information

Number of reviews
370
Accommodation
128 Apartments
Lowest Price
€148
Highest Price
€455

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find 18 accommodation options in Chester. Though there aren't many apartments, we can help you search for accommodation with similar amenities. When you search for a place to stay on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. You can also filter by similar property types like holiday 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 a good option for you?
An apartment features a kitchen for convenient meals, and is usually more spacious than a traditional hotel room. Apartments are a good option for solo travellers who want to stay in at night and plan out their next day, but also for families who want the conveniences of home.
What's a favourite apartment for my stay in Chester?
Here are some of the top apartments in the area: Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer: Located 18.3 mi/29.5 km away in Beacon . Amenities include a Smart TV . Access to on-site laundry facilities is available on site . Modern penthouse suite in a restored grain tower with private roof deck.: It's situated in Warwick , 8.8 mi/14.1 km away. Includes free WiFi, a balcony and a Smart TV . Spectacular Log Home Estate North Wing Apt: Located 22.1 mi/35.5 km away in Marlboro . A balcony, a dining area and a Smart TV are included . Access to on-site laundry facilities is available on site . Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!: Located in Wallkill , 17.9 mi/28.7 km from Chester. Includes free WiFi, a balcony and a Smart TV . Access to on-site laundry facilities is available on site .
What can I expect from the weather during my trip to 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 temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm 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, Museum Village and Goosepond Mountain State Park 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 save you time when you get to your destination. Fly into Newburgh, NY (SWF-Stewart Intl.), which is located 13.5 mi (21.7 km) from the heart of the city. Otherwise, you can search for flights to 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.