Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Chester

Our top choices for Chester vacation rentals

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is ￥27,751
￥45,421 total
includes taxes & fees
Oct 1 - Oct 2
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Smart TV, fireplace

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

9.4 out of 10, Exceptional, (38)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
The price is ￥21,123
￥44,419 total
includes taxes & fees
Oct 3 - Oct 4
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (35)
"Great place for a quiet stay"
The price is ￥40,593
￥52,266 total
includes taxes & fees
Sep 28 - Sep 29
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"Fortunate to have found the time to spend a long weekend by the lake. Just the right remedy for our usual fast-paced schedules. Caught a beautiful sunset the first evening but every day was just as enjoyable."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
Property grounds

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

10.0 out of 10, Exceptional, (50)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is ￥16,606
￥40,067 total
includes taxes & fees
Oct 1 - Oct 2
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (22)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is ￥30,136
￥75,508 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Interior

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

9.8 out of 10, Exceptional, (12)
"This property has exactly what we were looking for to spend a long weekend and create new memories. The welcoming atmosphere and breathtaking views offer a unique experience. Jones was easily accessible to respond to any questions. We will certainly come and definitely recommend this property to family and friends. "
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
Outdoor pool, a heated pool

Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

9.8 out of 10, Exceptional, (86)
"Such a magical property! I came here with some friends for my birthday weekend and we had the most incredible time. The space- both indoors and out, is even more beautiful than the pictures (which never happens!). Everything was very clean and well kept. And the property manager was very supportive and communicative throughout. Providing lots of helpful information beforehand, and stayed in touch during my stay, even over the smallest things. We came during the summer but would love to come back...
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
A luxurious stay.
Smart TV

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is ￥18,599
￥42,583 total
includes taxes & fees
Sep 30 - Oct 1
A luxurious stay.
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234
Outdoor pool, a heated pool

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234

10.0 out of 10, Exceptional, (4)
"This property was comfortable, quaint and clean. Perfect little weekend getaway. We definitely plan on staying here again. "
The price is ￥16,237
￥36,389 total
includes taxes & fees
Oct 2 - Oct 3
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Terrace/patio

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

10.0 out of 10, Exceptional, (33)
"We had a nice and relaxing time in beautiful surroundings. Thank you for having this cabin. We really enjoyed the sunsets reflecting off the lake!"
The price is ￥25,832
￥55,927 total
includes taxes & fees
Oct 13 - Oct 14
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Rustic Cabin in Fishkill!
Exterior

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is ￥40,593
￥61,576 total
includes taxes & fees
Sep 29 - Sep 30
Rustic Cabin in Fishkill!
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Smart TV, video games, DVD player, foosball

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

9.4 out of 10, Exceptional, (39)
"The rental was lovely. We all went up for friends wedding great location and am going back to check out the alien museum. "
The price is ￥25,108
￥63,333 total
includes taxes & fees
Oct 1 - Oct 2
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Outdoor dining

Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental

10.0 out of 10, Exceptional, (2)
"Beautiful home, on a quiet street. Ample view from the living room, kitchen and deck/dock. We loved have a little private beach area for my daughter. The game room was such a fun bonus!! We will definitely be back !! "
The price is ￥29,800
￥68,593 total
includes taxes & fees
Sep 29 - Sep 30
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Romantic spot above restaurant., ideal for the gourmet
Exterior

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (3)
"Hosts communicated well, the room was spacious and clean, and the restaurant downstairs is spectacular. "
The price is ￥22,142
￥28,722 total
includes taxes & fees
Sep 28 - Sep 29
Romantic spot above restaurant., ideal for the gourmet
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Property grounds

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

10.0 out of 10, Exceptional, (66)
"We had a great stay."
The price is ￥20,894
￥43,056 total
includes taxes & fees
Sep 29 - Sep 30
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Greenwood Lake Lakefront Luxury
Property grounds

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (142)
"We had the best time. The home was so clean and comfortable, and the views were beautiful. Cheryl is an amazing host and has stocked the home with everything needed to enjoy your stay. We hope to visit again!"
Greenwood Lake Lakefront Luxury
Large,Cozy,Bright Apartment, Business Themed.
Interior

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is ￥59,782
￥99,911 total
includes taxes & fees
Sep 26 - Sep 27
Large,Cozy,Bright Apartment, Business Themed.
Chestnut on Willow Lake
Dining tables

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is ￥59,044
￥85,373 total
includes taxes & fees
Sep 29 - Sep 30
Chestnut on Willow Lake
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Terrace/patio

Cozy Loft Cabin high above Bashakill Wildlife Refuge

9.4 out of 10, Exceptional, (25)
"A fantastic little getaway after a wonderful day of hiking the Catskills! Vinny & Josh were perfect hosts and the property is fantastic! Will definitely be back! "
The price is ￥17,713
￥28,208 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Loft Cabin high above Bashakill Wildlife Refuge
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Convenient, great parking, quiet, comfortable room with a friendly staff."
Gay 2-night trip
Posted 6 hours ago
Quality Inn & Suites Fishkill South near I-84

Find out more about Chester

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:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Chester offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Chester?

Expedia has 11 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. You’ll find favorite places to visit like LEGOLAND® New York and Woodbury Common Premium Outlets in the larger area.

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.