Chester Holiday Rentals

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Check prices for these dates

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Holiday Rentals in Chester

Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
Zack C.
The price is HK$827
HK$1,423 total
includes taxes & fees
21 Oct - 22 Oct
Cozy 1-bedroom retreat minutes from West Point!
Fridge, microwave, oven, stovetop
Cabin in the heart of the Hudson Valley, Cabin 3
Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (13)
"We had a great stay, everything you need is provided. Would recommend to anyone."
Bill W.
The price is HK$1,080
HK$1,854 total
includes taxes & fees
21 Oct - 22 Oct
Cabin in the heart of the Hudson Valley, Cabin 3
Terrace/patio
Cozy Loft Cabin high above Bashakill Wildlife Refuge
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! "
Kristine G.
The price is HK$933
HK$1,485 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Children’s area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (11)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
Teresa
The price is HK$1,154
HK$2,235 total
includes taxes & fees
27 Oct - 28 Oct
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
1 bedroom, WiFi, bed sheets
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (31)
"Great place! "
Carol M.
The price is HK$855
HK$1,888 total
includes taxes & fees
11 Nov - 12 Nov
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Interior
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.6 out of 10, Exceptional, (4)
"The Warwick Inn is an amazing stay for anyone trying to escape for a few days. The rooms were amazing, spacious, and comfortable. Gabriela was amazing at setting up our check-in and was always available for any questions we had. Highly recommend. "
Nicolas
The price is HK$657
HK$1,166 total
includes taxes & fees
20 Oct - 21 Oct
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior detail
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
10.0 out of 10, Exceptional, (12)
"Great Unit."
Rudy R.
The price is HK$909
HK$2,374 total
includes taxes & fees
5 Nov - 6 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Fridge, microwave, oven, stovetop
Cabin in the Heart of the Hudson Valley, Cabin 1
Cabin in the Heart of the Hudson Valley, Cabin 1
9.8 out of 10, Exceptional, (28)
"Our cabin was cozy, comfortable and clean with high-quality sheets and towels. I would stay here again if I'm ever in the area. "
Jeff Scott D.
The price is HK$1,080
HK$1,854 total
includes taxes & fees
19 Oct - 20 Oct
Cabin in the Heart of the Hudson Valley, Cabin 1
Interior
Cozy Cottage with Grill | Walk to Lake
Cozy Cottage with Grill | Walk to Lake
9.8 out of 10, Exceptional, (21)
"Our second time staying at the cottage and we love it so much. So comfortable. So close to the lake, and just fabulous!"
CarlyS
The price is HK$1,414
HK$3,813 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Cottage with Grill | Walk to Lake
Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge
Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (23)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
Harriet
The price is HK$637
HK$1,489 total
includes taxes & fees
17 Nov - 18 Nov
Dream getaway apartment in the foot of Gunks Ridge
Interior
Hike & Fish: Outdoor Retreat Near Trails
Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
The price is HK$1,422
HK$2,378 total
includes taxes & fees
19 Oct - 20 Oct
Hike & Fish: Outdoor Retreat Near Trails
Outdoor dining
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
Stephen H.
The price is HK$1,088
HK$1,694 total
includes taxes & fees
20 Oct - 21 Oct
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Smart TV
Grant - A Tranquil One Bedroom Steps from River
Grant - A Tranquil One Bedroom Steps from River
9.6 out of 10, Exceptional, (35)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
Zohar
The price is HK$839
HK$2,031 total
includes taxes & fees
21 Oct - 22 Oct
Grant - A Tranquil One Bedroom Steps from River
Property grounds
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!
10.0 out of 10, Exceptional, (68)
"This is a beautiful property. The apartment was very clean and comfortable with everything we could need. The view was spectacular and the host made it so easy to check in and out. This property is top of the list for our next visit."
Judy F.
The price is HK$956
HK$1,897 total
includes taxes & fees
4 Nov - 5 Nov
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Interior
Villa Verde B&B, bsm, Greenwood Lake NY
Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
Tara
The price is HK$1,453
HK$2,567 total
includes taxes & fees
19 Oct - 20 Oct
Villa Verde B&B, bsm, Greenwood Lake NY
Exterior
Hello Small Stone
Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
John H.
The price is HK$1,294
HK$3,231 total
includes taxes & fees
19 Oct - 20 Oct
Hello Small Stone
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (41)
"Adorable place to stay in an adorable town! "
Mary L.
The price is HK$855
HK$1,816 total
includes taxes & fees
5 Nov - 6 Nov
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
TV, fireplace
Cozy Haven: A Romantic Retreat in our Tiny House!
Cozy Haven: A Romantic Retreat in our Tiny House!
7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
Yidel
The price is HK$1,166
HK$2,332 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Haven: A Romantic Retreat in our Tiny House!
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (63)
"Such a cute place to stay"
Melissa
The price is HK$1,049
HK$2,019 total
includes taxes & fees
21 Oct - 22 Oct
Cozy country efficiency in the Hudson Valley
Property grounds
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
2.5 star property
9.2 out of 10, Wonderful, (5)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
Jonathan O.
The price is HK$777
HK$1,947 total
includes taxes & fees
3 Nov - 4 Nov
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
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

Hampton Inn Nanuet

Hampton Inn Nanuet

10/10 Excellent
"Great location close to everything but far enough away from everything!"
Tyler 1-night trip
Posted 2 days ago
Hampton Inn Nanuet

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 holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Castle Fun Center, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffee shops during your trip.

What are some of the best holiday rentals that Chester has to offer?

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out: This holiday home rental outside of Chester is located in the mountains, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chester?

Expedia has 11 holiday 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 favourite places to visit such as LEGOLAND® New York and Woodbury Common Premium Outlets in the wider area.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.