Apartments in Chester for Rent

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Chester apartments

Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!

Apartment in 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.
$157 nightly
The price is $169
Dec 14 - Dec 15
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment in Highland Falls

9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
$273 nightly
The price is $277
Dec 11 - Dec 12
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge

Apartment in 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
$181 nightly
The price is $184
Dec 11 - Dec 12
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Apartment in Beacon

10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
$211 nightly
The price is $243
Dec 14 - Dec 15
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Private kitchen
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Apartment in 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.
$266 nightly
The price is $314
Dec 11 - Dec 12
Total with taxes and fees
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Fridge, microwave, oven, stovetop
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Apartment in 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.
$229 nightly
The price is $252
Dec 14 - Dec 15
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Fridge, microwave, oven, stovetop
Local Artist Inspired | Walk to WestPoint + King Bed

Apartment in Highland Falls

9.2 out of 10, Wonderful, (9)
"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.
$409 nightly
The price is $415
Dec 11 - Dec 12
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
Property grounds
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Apartment in Wallkill

10.0 out of 10, Exceptional, (71)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
$209 nightly
The price is $234
Dec 11 - Dec 12
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Smart TV
Grant - A Tranquil One Bedroom Steps from River

Apartment in Newburgh

9.6 out of 10, Exceptional, (39)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
$246 nightly
The price is $278
Dec 29 - Dec 30
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
Apartment (1 Bedroom) | Interior
Explore & Work! Stylish Washington Heights Duplex

Apartment in Newburgh

3.0 star property
Explore & Work! Stylish Washington Heights Duplex
Exterior
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.

Apartment in 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.
$246 nightly
The price is $276
Dec 14 - Dec 15
Total with taxes and fees
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Fridge, microwave, oven, stovetop
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Apartment in Warwick

10.0 out of 10, Exceptional, (40)
"This was the best place to stay. Host was so nice to us. If we are in the area again we would definitely stay here again. "
United States
Eileen H.
$213 nightly
The price is $241
Jan 4 - Jan 5, 2026
Total with taxes and fees
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley

Apartment in Newburgh

9.8 out of 10, Exceptional, (66)
"Such a cute place to stay"
United States
Melissa
$277 nightly
The price is $327
Dec 11 - Dec 12
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.

Apartment in Beacon

10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
$241 nightly
The price is $273
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lux APT Your home away from home.
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Apartment in Beacon

9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$205 nightly
The price is $236
Dec 14 - Dec 15
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Microwave, oven, stovetop, dishwasher
Modern Hudson Valley Apt 202 - King/Queen/Twin

Apartment in Montgomery

9.8 out of 10, Exceptional, (15)
"Such a cute apartment and very clean. Everything is new and the town is very quaint!! Close to other things like shopping and restaurants. Definitely would stay again and recommend to anyone looking for a clean, quiet and safe area to stay."
United States
Michael V.
$237 nightly
The price is $270
Dec 11 - Dec 12
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
Fridge, microwave, stovetop, coffee/tea maker
Explore & Work! Stylish Washington Heights Duplex

Apartment in Newburgh

2.0 star property
$282 nightly
The price is $332
Dec 11 - Dec 12
Total with taxes and fees
Explore & Work! Stylish Washington Heights Duplex
Fridge, microwave, oven, stovetop
The Wine House, Sitting atop of Warwick's brand new Wine Bar

Apartment in Warwick

10.0 out of 10, Exceptional, (26)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
$227 nightly
The price is $256
Dec 11 - Dec 12
Total with taxes and fees
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Exterior
Villa Verde B&B, Greenwood Lake NY, 1

Apartment in 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
$233 nightly
The price is $264
Jan 4 - Jan 5, 2026
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
Outdoor dining
The Appalachian at Mountain Creek

Apartment in Vernon Township

$209 nightly
The price is $225
Dec 11 - Dec 12
Total with taxes and fees
The Appalachian at Mountain Creek
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Clean nice"
candy 1-night trip
Posted 14 hours ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Chester

Chester Apartments information

Number of reviews
416
Accommodation
128 Apartments
Lowest Price
$169
Highest Price
$415

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: Modern penthouse suite in a restored grain tower with private roof deck.: Situated in Warwick, 8.8 mi/14.1 km from the heart of Chester. Includes free WiFi and Smart TVs. 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. Unicorn Studio - Historic Newburgh near Beacon + Hiking: It's located in Newburgh, 17 mi/27.4 km away. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!: Located 15.7 mi/25.3 km away in Highland Falls. Sofa beds and Smart TVs are included. Access to onsite laundry facilities is available on site. Cozy country efficiency in the Hudson Valley: It's located in Newburgh, 19.6 mi/31.5 km from Chester. Includes free WiFi, private patios, and fireplaces.
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.

Explore a world of travel with Expedia