Chester Holiday Rentals

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Our top choices for Chester holiday rentals

Forava Cabins - Tiny Cabin in the Woods

Forava Cabins - Tiny Cabin in the Woods
3.0 star property
Ringwood
10.0 out of 10, Exceptional, (1 review)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
The price is AU$412
includes taxes & fees
5 Feb - 6 Feb
Forava Cabins - Tiny Cabin in the Woods

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$271
includes taxes & fees
4 Feb - 5 Feb
Cozy 1-bedroom retreat minutes from 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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$484
includes taxes & fees
1 Feb - 2 Feb
House on the Babbling Brook- Quiet 2BR + King Bed!

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, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
The price is AU$233
includes taxes & fees
1 Feb - 2 Feb
Dream getaway apartment in the foot of Gunks Ridge

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, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is AU$369
includes taxes & fees
1 Feb - 2 Feb
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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
9.2 out of 10, Wonderful, (9 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$229
includes taxes & fees
2 Feb - 3 Feb
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is AU$638
includes taxes & fees
3 Feb - 4 Feb
Rustic Cabin in Fishkill!

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, (59 reviews)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
The price is AU$710
includes taxes & fees
1 Feb - 2 Feb
Country House w/Hot Tub, Deck, Grill & Fire Pit

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is AU$353
includes taxes & fees
1 Feb - 2 Feb
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

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$416
includes taxes & fees
30 Jan - 31 Jan
Villa Verde B&B, bsm, Greenwood Lake NY

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is AU$503
includes taxes & fees
4 Feb - 5 Feb
Lovely 3BR Home with parking-Walk to WP Gate!

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is AU$406
includes taxes & fees
4 Feb - 5 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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$586
includes taxes & fees
30 Jan - 31 Jan
Contemporary Cozy Cottage

Creekfront Cabin Sauna & Hot Tub Hikers Hollow

Creekfront Cabin Sauna & Hot Tub Hikers Hollow
Cuddebackville
10.0 out of 10, Exceptional, (5 reviews)
"Definitely recommend to anyone looking to get away from the busyness for a while! It's a beautiful home away from home!"
United States
Aaron B.
The price is AU$796
includes taxes & fees
2 Feb - 3 Feb
Creekfront Cabin Sauna & Hot Tub Hikers Hollow

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.4 out of 10, Exceptional, (57 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is AU$452
includes taxes & fees
31 Jan - 1 Feb
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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)
"The property was amazing and Kimberly was the greatest host! Can’t wait to visit again!"
United States
Logan W.
The price is AU$760
includes taxes & fees
1 Feb - 2 Feb
Modern penthouse suite in a restored grain tower with private roof deck.

Serene Rustic Retreat with Lake

Serene Rustic Retreat with Lake
Cuddebackville
10.0 out of 10, Exceptional, (8 reviews)
"Amazing stay and beautiful home!"
United States
Koby A.
The price is AU$686
includes taxes & fees
30 Jan - 31 Jan
Serene Rustic Retreat with Lake

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)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is AU$419
includes taxes & fees
1 Feb - 2 Feb
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Rustic Lakefront Studio w Deck Workspace

Rustic Lakefront Studio w Deck Workspace
2.0 star property
Monroe
Rustic Lakefront Studio w Deck Workspace

Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room

Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room
West Milford
10.0 out of 10, Exceptional, (4 reviews)
"The property was spotless, comfortable, and had everything we needed. The location was perfect—close to attractions yet quiet and relaxing. The hosts were amazing, welcoming and very responsive, they were welling to help us at all times and they may made sure the whole experience was smooth and enjoyable. We’d definitely stay here again!"
United States
Bana S.
The price is AU$795
includes taxes & fees
1 Feb - 2 Feb
Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room
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$342 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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. While here, Goosepond Mountain State Park and Museum Village 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.