Chester Holiday Rentals

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Our top choices for Chester holiday 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 AU$295
includes taxes & fees
12 May - 13 May
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 AU$288
includes taxes & fees
17 May - 18 May
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 AU$278
includes taxes & fees
12 May - 13 May
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, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is AU$293
includes taxes & fees
12 May - 13 May
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 AU$387
includes taxes & fees
27 May - 28 May
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 AU$449
includes taxes & fees
10 May - 11 May
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 AU$424
includes taxes & fees
12 May - 13 May
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 AU$344
includes taxes & fees
10 May - 11 May
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 AU$208
includes taxes & fees
11 May - 12 May
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 AU$616
includes taxes & fees
17 May - 18 May
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, (135 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is AU$441
includes taxes & fees
15 May - 16 May
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 AU$468
includes taxes & fees
10 May - 11 May
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 AU$658
includes taxes & fees
10 May - 11 May
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 AU$706
includes taxes & fees
10 May - 11 May
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 AU$333
includes taxes & fees
10 May - 11 May
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 AU$554
includes taxes & fees
11 May - 12 May
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 AU$393
includes taxes & fees
11 May - 12 May
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 AU$556
includes taxes & fees
10 May - 11 May
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 AU$214
includes taxes & fees
14 May - 15 May
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 AU$402
includes taxes & fees
17 May - 18 May
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

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$329 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?

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

How many holiday rentals are there in Chester?

Expedia has 9 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.