Apartments in Chester for Rent

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  • Upfront pricing

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

Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

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.
$175 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
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!
Highland Falls
9.8 out of 10, Exceptional, (15 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Jan 19 - Jan 20
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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)
"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
$162 nightly
The price is $165
Jan 26 - Jan 27
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
3 bedrooms, desk, iron/ironing board, travel crib

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 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.
$356 nightly
The price is $359
Jan 20 - Jan 21
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
Apartment | 1 bedroom

Natural Getaway at Orchard Farm Lakeside Retreat

Natural Getaway at Orchard Farm Lakeside Retreat
2.0 star property
Monroe
$210 nightly
The price is $238
Jan 19 - Jan 20
Total with taxes and fees
Natural Getaway at Orchard Farm Lakeside Retreat
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.
$207 nightly
The price is $238
Jan 19 - Jan 20
Total with taxes and fees
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
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.
$260 nightly
The price is $307
Jan 22 - Jan 23
Total with taxes and fees
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
Beacon
9.8 out of 10, Exceptional, (42 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$203 nightly
The price is $234
Jan 20 - Jan 21
Total with taxes and fees
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.
Beacon
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and great place to stay. "
United States
Charlene D.
$241 nightly
The price is $273
Feb 1 - Feb 2
Total with taxes and fees
Lux APT Your home away from home.
1 bedroom, free WiFi, bed sheets, wheelchair access

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, (34 reviews)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
$230 nightly
The price is $260
Jan 20 - Jan 21
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
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.
$272 nightly
The price is $301
Feb 9 - Feb 10
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Desk, WiFi, bed sheets

Studio Retreat | Near Woodbury Commons & Legoland

Studio Retreat | Near Woodbury Commons & Legoland
2.0 star property
Monroe
$198 nightly
The price is $201
Jan 19 - Jan 20
Total with taxes and fees
Studio Retreat | Near Woodbury Commons & Legoland
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.
$243 nightly
The price is $273
Jan 21 - Jan 22
Total with taxes and fees
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
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
$241 nightly
The price is $265
Jan 18 - Jan 19
Total with taxes and fees
Walk to WP Gate + Free Parking!
Apartment | 1 bedroom

Bright Studio Retreat w Deck Nature Views

Bright Studio Retreat w Deck Nature Views
2.0 star property
Monroe
$290 nightly
The price is $328
Jan 19 - Jan 20
Total with taxes and fees
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
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
$236 nightly
The price is $267
Jan 16 - Jan 17
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
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)
"Such a cute place to stay"
United States
Melissa
$279 nightly
The price is $330
Jan 16 - Jan 17
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
Microwave, oven, stovetop, dishwasher

Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (15 reviews)
"We had a great stay!! I booked for a “get ready” spot for my wedding and it was everything I could have dreamed of. Everything was perfect and very clean! Can’t wait to book again Very centrally located near some amazing small boutiques, a couple restaurants. The town seemed like a popular spot on the weekend! "
United States
Tiffani H.
$237 nightly
The price is $270
Jan 19 - Jan 20
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
Outdoor dining

The Appalachian at Mountain Creek

The Appalachian at Mountain Creek
Vernon Township
$224 nightly
The price is $241
Jan 28 - Jan 29
Total with taxes and fees
The Appalachian at Mountain Creek
Dining

Hudson Valley Top Getaway with a River View B

Hudson Valley Top Getaway with a River View B
2.0 star property
Newburgh
$272 nightly
The price is $321
Jan 16 - Jan 17
Total with taxes and fees
Hudson Valley Top Getaway with a River View B
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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Good stay"
Cindy 1-night trip
Posted 2 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Chester

Chester Apartments information

Number of reviews
302
Accommodation
128 Apartments
Lowest Price
$165
Highest Price
$359

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. Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA: Located in Beacon, 17.8 mi/28.7 km away. Includes 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 18.3 mi/29.5 km away in Beacon. Amenities include Smart TVs. Access to onsite laundry facilities is available on site. Charming studio with Amazing hot tub a swimming pool,pool table.: Located in Newburgh, 17.5 mi/28.2 km from Chester. Includes private patios. An outdoor pool and a hot tub are 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.

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