A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Apartments in Chester for Rent

  • 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

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chester apartments

A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

1. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.4 out of 10, (18 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
$152 nightly
The price is $172
Oct 13 - Oct 14
Total with taxes and fees
Cottage Suites
A modern hotel room with a large bed, a seating area with leather chairs, and a view of the outdoors through large windows.

2. 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, (47 reviews)
"In the area for my nephew’s graduation. Loved walking around Warwick and checking out shops.Beautiful accommodations. Very clean, easy check in, comfortable bed. Appreciated the options for coffee and tea. Overall, a great stay."
United States
Gwenda M.
$209 nightly
The price is $236
Oct 7 - Oct 8
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
A hallway with a door labeled '302' and a keypad lock.

3. The Columbus Hotel - The Reimagined Suite - 52-304

The Columbus Hotel - The Reimagined Suite - 52-304
Middletown
$164 nightly
The price is $186
Sep 29 - Sep 30
Total with taxes and fees
The Columbus Hotel - The Reimagined Suite - 52-304
A dark blue door with a glass panel, flanked by two potted topiary trees, a welcome mat, and a wall-mounted light fixture.

4. Charming 2-bedroom apartment in the Village of Warwick

Charming 2-bedroom apartment in the Village of Warwick
Warwick
9.4 out of 10, Exceptional, (3 reviews)
"Clean, family friendly, close to everything."
United States
Milena P.
$270 nightly
The price is $305
Oct 5 - Oct 6
Total with taxes and fees
Charming 2-bedroom apartment in the Village of Warwick
A modern kitchen with wooden flooring, a dining area with a table and chairs, and a kitchen counter with appliances.

5. The Wine House

The Wine House
Warwick
10.0 out of 10, Exceptional, (38 reviews)
"Amazing place - we will definitely be back ."
United States
Robin
$246 nightly
The price is $278
Sep 29 - Sep 30
Total with taxes and fees
The Wine House

6. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (52 reviews)
"One of the cleanest VRBOs I ever stayed in - it smelled so good. Very cozy and had everything we needed. The location is great!"
United States
Tara K.
$214 nightly
The price is $242
Oct 13 - Oct 14
Total with taxes and fees
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

7. Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (20 reviews)
"Great hosts and great location!"
United States
Shelby A.
$256 nightly
The price is $294
Sep 29 - Sep 30
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

8. Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (101 reviews)
"We were very happy with the house and location, but what made it amazing was how great host was. Very accommodating and helpful with helping us out last minute. Would absolutely recommend working with this host again."
United States
Chris W.
$233 nightly
The price is $261
Oct 8 - Oct 9
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A modern hotel room with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view of the adjacent dining area.

9. The Columbus Hotel - The Sunny Studio - 52-302

The Columbus Hotel - The Sunny Studio - 52-302
Middletown
$184 nightly
The price is $208
Sep 29 - Sep 30
Total with taxes and fees
The Columbus Hotel - The Sunny Studio - 52-302
A staircase with a fire alarm and a row of lockers.

10. The Columbus Hotel - The Market Suite - 52-202

The Columbus Hotel - The Market Suite - 52-202
Middletown
$179 nightly
The price is $202
Sep 29 - Sep 30
Total with taxes and fees
The Columbus Hotel - The Market Suite - 52-202
A kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a coffee maker.

11. The Columbus Hotel - The City Suite - 89-201

The Columbus Hotel - The City Suite - 89-201
Middletown
$179 nightly
The price is $203
Sep 29 - Sep 30
Total with taxes and fees
The Columbus Hotel - The City Suite - 89-201
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$285 nightly
The price is $290
Oct 1 - Oct 2
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

13. 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, (31 reviews)
"Wonderful property will definitely book again."
United States
Jane G.
$177 nightly
The price is $179
Sep 30 - Oct 1
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
A living room with a fireplace, a painting, shelves with decorative items, and a television.

14. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$250 nightly
The price is $283
Oct 5 - Oct 6
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A stone pathway leading to a stone wall with a potted plant.

15. 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
$300 nightly
The price is $339
Sep 29 - Sep 30
Total with taxes and fees
Villa Verde B&B, Greenwood Lake NY, 1
A hotel with a central swimming pool, multiple balconies, and a distinctive yellow and brown facade.

16. Swiss Spot. Cozy 1-bedroom apartment in charming Vernon NJ with heated pools.

Swiss Spot. Cozy 1-bedroom apartment in charming Vernon NJ with heated pools.
Vernon Township
10.0 out of 10, Exceptional, (1 review)
"Had a lovely stay at Gretchen's Swiss Spot. The room and property were as described, and we had a great dip in the pool and hot tub out back. No issues to speak of; check-in/out and communication were seamless. Will bring the kids if we come back!"
United States
Brian F.
$185 nightly
The price is $209
Sep 29 - Sep 30
Total with taxes and fees
Swiss Spot. Cozy 1-bedroom apartment in charming Vernon NJ with heated pools.
A bedroom with a bed, a desk, a chair, a potted plant, and a window.

17. 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.
$235 nightly
The price is $265
Sep 29 - Sep 30
Total with taxes and fees
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
A wooden cabin with a porch, a door, and a window.

18. Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
Wurtsboro
10.0 out of 10, Exceptional, (12 reviews)
"Very kind and nice owner, brand new building have everything you needed"
United States
Ayur
$232 nightly
The price is $262
Sep 29 - Sep 30
Total with taxes and fees
Close to Trails: Studio w/ Water Views
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

19. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$398 nightly
The price is $403
Sep 29 - Sep 30
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed

20. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$212 nightly
The price is $234
Sep 30 - Oct 1
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
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

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Was a pleasant overnight stay"
david 1-night trip
Posted 11 hours ago
Ramada by Wyndham Newburgh/West Point

Find out more about Chester

Chester Apartments information

Number of reviews
352
Accommodation
145 Apartments
Lowest Price
$172
Highest Price
$403

Frequently asked questions

What's it like to stay at an apartment in Chester?
You'll find plenty of places to stay in Chester with 21 hotels and other lodging accommodations. Though there aren't many apartments, we can help you locate accommodations that are similar. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also filter by similar properties such as condos, vacation homes, or cottages. You might want to visit the area's shops and enjoy its restaurants. While in the region, visit favorite sights like Woodbury Common Premium Outlets.
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: Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY: Situated in Chester, 3 mi/4.8 km from the heart of Chester. 1 Queen Bed | Non-Smoking, Kitchen: Located 22.8 mi/36.7 km away in Fishkill. Free WiFi and Smart TVs are included. 2 Full Beds | Non-Smoking, Kitchen: It's situated in Fishkill, 22.8 mi/36.7 km away. Includes free WiFi and Smart TVs. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill: 22.8 mi/36.7 km away in Fishkill. Free WiFi and Smart TVs are included. Studio 6 Fishkill|King bed|Hearing Access|Kitchen: It's located in Fishkill, 22.8 mi/36.7 km from Chester. Includes free WiFi and Smart TVs.
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. Cultural attractions include Museum Village and Sugar Loaf Performing Arts Center, whereas The Rock Sports Complex is one spot to enjoy nature. While here, Castle Fun Center 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 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