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Next weekend

21 Saf. - 23 Saf.

In two weeks

28 Saf. - 2 Rab. I

In one month

14 Rab. I - 16 Rab. I

In two months

11 Rab. II - 13 Rab. II

Compare Apartments in Chester with updated reviews, rates, and availability.

"Great location near west point. Ample parking. Walkable. Clean"

"Fantastic little spot! Super cute and near everything! Absolutely enjoyed our stay and would stay again!"

"Nice."

SAR 852 total

includes taxes & fees

12 Feb - 13 Feb

The front view of the Appalachian building

"We have stayed in this apartment before loved it then and again now. Nice clean space with everything we needed. My son slept on the couch bed and it was super comfortable. Hosts are great. Just an elevator ride to ski and snowboard. "

"I am in travel and familiar with stays at hotel, etc. This felt like we were staying at a European Hotel. We totally recommend it.Carol"

SAR 953 total

includes taxes & fees

18 Feb - 19 Feb

"Lovely location, conveniently situated next to West Point. Highly recommend if you are looking for a place to stay for homecoming weekend or simply visiting the area. Added convenience is its close proximity to the local bakery (repeat customer) and the pizza place wherein I think my kids did indeed lick their plates clean."

"We had a great visit at this apartment - it was in the perfect location and the host was very responsive/helpful as we planned around the weather. We would definitely stay again! "

SAR 1,843 total

includes taxes & fees

12 Feb - 13 Feb

"During a prior workshop, the instructor told us after booking that she recommended booking a different location 30 mins away. I kept that booking, but I tried to avoid issues this time by booking last minute. Unfortunately the Guide cancelled due to health issues the day after booking this one. It was non-refundable, but I am thankful that Kelly was willing to work with me and change the dates. Otherwise, I would have had to come up on my own and do the best I could without guidance. Thank you!"

SAR 730 total

includes taxes & fees

12 Feb - 13 Feb

"Great location on Beacon’s Main Street. Central to everything. Lovely studio had everything we needed. "

SAR 872 total

includes taxes & fees

23 Feb - 24 Feb

"We were in town for the state high school soccer championships over the weekend and needed a pet friendly place to stay. This place was just right and had everything we needed. It was very cozy and very private. If we are ever in the area again, we would not hesitate to stay here. "

"Beautiful apartment with everything needed. The owners are very responsive and kind and quickly assisted when an appliance quit working. The only downside was the upstairs neighbors were loud and the parking is a little difficult since it was assigned away from the home. "

"This property is adorable and very comfortable. The building is unique and has a lot of character and the hosts were excellent. We will stay here again. Thank you for a great visit."

Beacon Vacation Rental | 1BR | 1BA | 2 Stairs Required to Enter

"A hidden gem...loved the apartment, and the hosts were fantastic!"

"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!"

SAR 831 total

includes taxes & fees

10 Mar - 11 Mar

"The home was easy to find. It was very clean. Easy access to get in. It had all the amenities listed. James was very responsive. We really enjoyed our time there."

"Lovely, peaceful home away from home. "

"Great location. Quiet surroundings.."

Newburgh Vacation Rental | 1BR | 1BA | 800 Sq Ft | Stairs Required

"Great apartment and great area to visit. Joyce and Mike are wonderful hosts and are most welcoming. This is our 2nd stay here, and we would definitely stay again!"

"This little attached apartment was the perfect size for me, and I felt very safe. I loved being at the top end of the cul de sac so it was quiet and there was an amazing view from the deck looking over and down the Hudson River. I had beautiful sunrises and the lights at night along the river were so pretty. The bedroom/living/dining room was perfect for one. The electric fireplace gave the room a cozy feel, the bed and couch were comfy, and there was plenty of hot water for showers and...

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"Spectacular view and very convenient to USMA. "

SAR 919 total

includes taxes & fees

12 Feb - 13 Feb

"Great place for family ski vacation. Apt was clean, with amenities for cooking. Great fireplace. The ski areas are very kid friendly. The bunny slope was carved up into different trails for learning different skills. Didn’t need to drive to get things. Everything for a great stay was right on site."

SAR 1,210 total

includes taxes & fees

13 Feb - 14 Feb

"We enjoyed our stay at this condo. There was plenty of space for us to hang out and sleep. We used the kitchen a lot and for the most part it was well equipped. We could have used more things like larger bowls to mix things or for chips. The downstairs bathroom shower could also use a curtain so that the water doesn’t get everywhere. The condo was easy to find and check in. The owner reached out to make sure we were good which was nice. Overall our family was happy with the unit "

SAR 1,666 total

includes taxes & fees

3 Mar - 4 Mar

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Frequently asked questions

What's it like to stay at an apartment in Chester?

You’ll find 15 hotels and other accommodations in Chester. 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: Walk to WP Gate + Free Parking!: Situated in Highland Falls, 15.8 mi/25.5 km from the heart of Chester. Includes free WiFi. 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. Stay in the heart of Greenwood Lake minutes away from the lake: It’s situated in Greenwood Lake, 9.6 mi/15.5 km away. Includes free WiFi, private patios, and Smart TVs. Modern penthouse suite in a restored grain tower with private roof deck.: 8.8 mi/14.1 km away in Warwick. Free WiFi and Smart TVs are included. Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!: It’s located in Wallkill, 17.9 mi/28.7 km from Chester. Includes free WiFi, private balconies, 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. The Rock Sports Complex and Goosepond Mountain State Park are a couple of scenic spots to enjoy the outdoors, whereas Museum Village is one of the cultural attractions. Castle Fun Center and Woodbury Common Premium Outlets are a couple of places you’ll find in the larger area.

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.

Search Apartments in Chester

Plan, book, stay with confidence

Check prices for these dates

Compare Apartments in Chester with updated reviews, rates, and availability.

Walk to WP Gate + Free Parking!

Stay in the heart of Greenwood Lake minutes away from the lake

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Comfy Studio at the Appalachian building - Mountain Creek Resort, Vernon, NJ

Luxury Loft on Main Street -Steam Shower, Theater Seats, Views, Designer Kitchen

Local Artist Inspired | Walk to WestPoint + King Bed

Modern penthouse suite in a restored grain tower with private roof deck.

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

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

Cozy country efficiency in the Hudson Valley

Entire 1 Bedroom Apartment in Lovely Family Vacation Lake House. Pets welcome!

Modern and Bright with office+ walk to nearby Waterfront, 1st FL.

Charming Beacon Apt w/ Fire Pit: Near Hiking!

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

Heritage Trail Farmhouse

Vernon Condo w/ Deck, Near Appalachian Trail!

Vernon Township Condo w/ Mountain Views!

Historic Hudson Valley Apartment: River View!

Spectacular Log Home Estate North Wing Apt

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Other property types in Chester

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

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