Chester Holiday Rentals

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Our top choices for Chester holiday rentals

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, (61 reviews)
"Very good host "
United States
Binyomin
The price is AU$711
includes taxes & fees
31 Mar - 1 Apr
Country House w/Hot Tub, Deck, Grill & Fire Pit

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, (132 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is AU$422
includes taxes & fees
2 Apr - 3 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Ski House - ON THE SLOPE w/ hot tub

Ski House - ON THE SLOPE w/ hot tub
Vernon Township
10.0 out of 10, Exceptional, (20 reviews)
"Great location and great host."
United States
Rita L.
The price is AU$1,521
includes taxes & fees
20 Apr - 21 Apr
Ski House - ON THE SLOPE w/ hot tub

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."
United States
Lou F.
The price is AU$439
includes taxes & fees
2 Apr - 3 Apr
Cozy country efficiency in the Hudson Valley

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248
Vernon
10.0 out of 10, Exceptional, (12 reviews)
"Me, my partner and another couple stayed here for a summer weekend, the accommodations were so cozy, everything provided was great! The kitchen was fully equipped and we had pleasant breakfasts in the mornings, we went for the waterpark right around the corner, and we hope to return for the winter season. We all loved the stay! "
United States
David C.
The price is AU$718
includes taxes & fees
23 Mar - 24 Mar
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248

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

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is AU$755
includes taxes & fees
21 Mar - 22 Mar
Modern penthouse suite in a restored grain tower with private roof deck.

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is AU$434
includes taxes & fees
7 Apr - 8 Apr
Hike & Fish: Outdoor Retreat Near Trails

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #312

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #312
Vernon
9.6 out of 10, Exceptional, (32 reviews)
"Loved our stay. Highly recommend and we’d definitely stay again. "
United States
John R.
The price is AU$712
includes taxes & fees
22 Mar - 23 Mar
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #312

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is AU$390
includes taxes & fees
1 Apr - 2 Apr
Cabin in the heart of the Hudson Valley, Cabin 3

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)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is AU$390
includes taxes & fees
1 Apr - 2 Apr
Cabin in the Heart of the Hudson Valley, Cabin 1

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 AU$420
includes taxes & fees
24 Mar - 25 Mar
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (31 reviews)
"Home is very nicely furnished. Also, the backyard is great place to come and stargaze!! "
United States
Elizabeth S.
The price is AU$1,178
includes taxes & fees
22 Mar - 23 Mar
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AU$583
includes taxes & fees
2 Apr - 3 Apr
Contemporary Cozy Cottage

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
The price is AU$530
includes taxes & fees
21 Mar - 22 Mar
Villa Verde B&B, bsm, Greenwood Lake NY

1BR Mtn‑Front Condo at The Appalachian • Deck, Fireplace & Stunning Views #324

1BR Mtn‑Front Condo at The Appalachian • Deck, Fireplace & Stunning Views #324
Vernon
10.0 out of 10, Exceptional, (101 reviews)
"Great place to stay on weekend."
United States
Oleg
The price is AU$434
includes taxes & fees
22 Mar - 23 Mar
1BR Mtn‑Front Condo at The Appalachian • Deck, Fireplace & Stunning Views #324

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (25 reviews)
"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "
United States
Jacqueline
The price is AU$362
includes taxes & fees
26 Mar - 27 Mar
Cozy 2BR condo w/ valley views

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
8.8 out of 10, Excellent, (3 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
The price is AU$670
includes taxes & fees
31 Mar - 1 Apr
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is AU$628
includes taxes & fees
8 Apr - 9 Apr
Hello Small Stone
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

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$315 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9: This holiday home rental outside of Chester is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chester?

Expedia has 10 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. While here, Museum Village and Goosepond Mountain State Park are other places worth a visit.

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.