Chester Vacation Rentals

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Our top choices for Chester vacation rentals

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is ¥16,807
¥33,596 total
includes taxes & fees
May 14 - May 15
Historic Cabin with Pool & Fire Pit

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.4 out of 10, Exceptional, (29 reviews)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
The price is ¥17,021
¥31,542 total
includes taxes & fees
Jun 8 - Jun 9
Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is ¥20,278
¥31,567 total
includes taxes & fees
May 14 - May 15
Cabin in the heart of the Hudson Valley, Cabin 4

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ¥19,361
¥35,662 total
includes taxes & fees
May 27 - May 28
Cozy 1-bedroom retreat minutes from West Point!

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is ¥26,565
¥44,192 total
includes taxes & fees
May 14 - May 15
Cabin in the Heart of the Hudson Valley, Cabin 1

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is ¥31,438
¥51,022 total
includes taxes & fees
Jun 3 - Jun 4
Luxury House Near West Point

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, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is ¥18,124
¥48,363 total
includes taxes & fees
May 27 - May 28
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (56 reviews)
"Great location and quiet just like we like it. Unit was very charming."
Canada
Thomas
The price is ¥18,863
¥39,994 total
includes taxes & fees
Jun 3 - Jun 4
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

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (16 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is ¥13,475
¥23,804 total
includes taxes & fees
May 27 - May 28
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is ¥38,512
¥70,214 total
includes taxes & fees
May 20 - May 21
Hike & Fish: Outdoor Retreat Near Trails

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ¥29,552
¥49,949 total
includes taxes & fees
May 28 - May 29
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
Vernon Township
10.0 out of 10, Exceptional, (35 reviews)
"Clean & organized, was a perfect location for our family trip."
United States
Rodney L.
The price is ¥27,508
¥53,721 total
includes taxes & fees
May 28 - May 29
Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

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

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ¥26,259
¥73,496 total
includes taxes & fees
May 14 - May 15
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (62 reviews)
"Very good host "
United States
Binyomin
The price is ¥51,716
¥93,874 total
includes taxes & fees
May 19 - May 20
Country House w/Hot Tub, Deck, Grill & Fire Pit

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is ¥31,362
¥37,209 total
includes taxes & fees
May 14 - May 15
Luxury home near West Point

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ¥24,428
¥66,108 total
includes taxes & fees
May 18 - May 19
House on the Babbling Brook- Quiet 2BR + King Bed!

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

1BR Updated Condo at The Appalachian • Deck, Fireplace & Stunning Views #251
vernon
10.0 out of 10, Exceptional, (5 reviews)
"Everything was great! Easy check in, clean well appointed amenities in the room and location was great! Thank you "
United States
Heather K.
The price is ¥22,478
¥47,616 total
includes taxes & fees
May 14 - May 15
1BR Updated Condo at The Appalachian • Deck, Fireplace & Stunning Views #251

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

Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking
vernon
9.4 out of 10, Exceptional, (31 reviews)
"Very nice property!"
United States
Chris E.
The price is ¥26,808
¥64,107 total
includes taxes & fees
May 14 - May 15
Luxe 10 guest Cabin/Skiing/Pools/Tennis/Gym/Hiking

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, (26 reviews)
"Clean and quiet."
United States
Ted
The price is ¥8,551
¥23,861 total
includes taxes & fees
May 14 - May 15
Dream getaway apartment in the foot of Gunks Ridge

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is ¥23,343
¥45,989 total
includes taxes & fees
May 14 - May 15
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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

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.