Chester Vacation Rentals from ￥37,023: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Chester?

Perfect and Spacious Hudson Valley Escape! : This vacation home rental near Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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Our top choices for Chester vacation rentals

Historic Cabin with Pool & Fire Pit

Montgomery

Sarah A.

￥33,596 total

includes taxes & fees

May 14 - May 15

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Wurtsboro

Marlon R.

￥31,542 total

includes taxes & fees

Jun 8 - Jun 9

Cabin in the heart of the Hudson Valley, Cabin 4

Newburgh

jennifer w.

￥31,567 total

includes taxes & fees

May 14 - May 15

Cozy 1-bedroom retreat minutes from West Point!

Highland Falls

Zack C.

￥35,662 total

includes taxes & fees

May 27 - May 28

1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Newburgh

Richard H.

￥44,192 total

includes taxes & fees

May 14 - May 15

Luxury House Near West Point

Highland Falls

￥51,022 total

includes taxes & fees

Jun 3 - Jun 4

Fridge, oven, stovetop, coffee/tea maker

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

Highland Falls

Liam C.

￥48,363 total

includes taxes & fees

May 27 - May 28

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

Beacon

Thomas

￥39,994 total

includes taxes & fees

Jun 3 - Jun 4

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Top Chester Hotel Reviews

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

"Great place! Thank you"

Studio 6 Extended Stay Fishkill Route 9 NY

2/10 Terrible

"BE CAREFUL* BE SAFE* Go somewhere else! During my stay, several staff members reported that the new management company is not paying them and that there is no longer an on-site manager. Therefore, I did not receive any services (room cleaning or bed change). Many long-term guests worked behind the counter, helped new guests, and cleaned the rooms. The credit card and personal information of guests are not safeguarded because long-stay guests were going in and out of the staff office and helping the housekeeping staff with cleaning rooms. "

Studio 6 Extended Stay Fishkill Westage Center NY

2/10 Terrible

"There was no one available at the front desk and there was a sign posted that said my reservation had been canceled and they apologize for any inconvenience. Since I arrived at about 9:15 p.m. I had no place to stay overnight and had to find another place. They had a telephone number for you to call if you arrived when the desk was closed however no one answered that phone. I ended up staying at another hotel 15 miles away."

Fairfield Inn & Suites by Marriott Goshen Middletown

2/10 Terrible

"I've had such an awful experience with this hotel that I will never again stay at a building with "Fairfield" in the name. I booked this hotel in part because they had a pool, and did not see anything in the app about it only being open seasonally. When we arrived, we found out the pool was closed. We checked out without a half hour or so, but they would not refund our stay. I reached out to the manager, and she refused to refund the night because the hotel was fully booked. (Be that as it may, rooms were still available that night on the app). "

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there vacation rentals in Chester?

Yes, you can find vacation rentals in Chester close to Castle Fun Center, or you can go with a more remote option if you'd like a relaxing place to stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffeehouses during your trip.

What are some of the best vacation home rentals in Chester?

Perfect and Spacious Hudson Valley Escape!: This vacation home rental near Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Chester?

Expedia has 9 vacation rentals for your stay in Chester.

What can I see and do in Chester?

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 are vacation rentals like in Chester?

Vacation rentals are privately owned properties you can reserve for several days or more in Chester. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Chester vacation rentals

Historic Cabin with Pool & Fire Pit

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cabin in the heart of the Hudson Valley, Cabin 4

Cozy 1-bedroom retreat minutes from West Point!

Cabin in the Heart of the Hudson Valley, Cabin 1

Luxury House Near West Point

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

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

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Hike & Fish: Outdoor Retreat Near Trails

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Country House w/Hot Tub, Deck, Grill & Fire Pit

Luxury home near West Point

House on the Babbling Brook- Quiet 2BR + King Bed!

1BR Updated Condo at The Appalachian • Deck, Fireplace & Stunning Views #251

Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking

Dream getaway apartment in the foot of Gunks Ridge

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Sleep Inn & Suites Monroe - Woodbury

Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Westage Center NY

Holiday Inn Express Hotel & Suites Chester by IHG

Sonesta Simply Suites Nanuet

DoubleTree by Hilton Hotel Nanuet

Fairfield Inn & Suites by Marriott Goshen Middletown

Hampton Inn Harriman Woodbury

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Find out more about Chester

Frequently asked questions

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