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Chester Holiday Rentals

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Our top choices for Chester holiday rentals

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, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$549
includes taxes & fees
24 June - 25 June
House on the Babbling Brook- Quiet 2BR + King Bed!

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$296
includes taxes & fees
25 June - 26 June
Cozy Loft Cabin high above Bashakill Wildlife Refuge

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (7 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is AU$340
includes taxes & fees
30 June - 1 July
TRANQUIL MOUNTAIN SOLITUDE

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful location, amazing balcony views"
United States
Hassan C.
The price is AU$367
includes taxes & fees
24 June - 25 June
Cozy 2BR condo w/ valley views

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, (29 reviews)
"Clean and quiet."
United States
Ted
The price is AU$267
includes taxes & fees
29 June - 30 June
Dream getaway apartment in the foot of Gunks Ridge

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
Warwick
8.6 out of 10, Excellent, (12 reviews)
"The bed was very comfortable! Loved the sitting area in the room! The downstairs of this location is an excellent restaurant! "
United States
Annette L.
The price is AU$227
includes taxes & fees
5 July - 6 July
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

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

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Vernon Township
9.4 out of 10, Exceptional, (54 reviews)
"Great convenient stay for a few days in the mountain!!! "
United States
rebecca l.
The price is AU$437
includes taxes & fees
6 July - 7 July
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Renovated 1 Bedroom Valley View

Renovated 1 Bedroom Valley View
Vernon Township
10.0 out of 10, Exceptional, (3 reviews)
"Room & Facilities are great."
United States
Elvis
The price is AU$343
includes taxes & fees
24 June - 25 June
Renovated 1 Bedroom Valley View

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$400
includes taxes & fees
25 June - 26 June
Cabin in the heart of the Hudson Valley, Cabin 3

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!
Wallkill
10.0 out of 10, Exceptional, (84 reviews)
"great location and nice host"
United States
christopher s.
The price is AU$347
includes taxes & fees
5 July - 6 July
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (41 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
The price is AU$388
includes taxes & fees
1 July - 2 July
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (19 reviews)
"great place tostay"
United States
Anonymous traveller
The price is AU$165
includes taxes & fees
24 July - 25 July
2 Full Beds | Non-Smoking, Kitchen

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is AU$422
includes taxes & fees
24 June - 25 June
Cozy country efficiency in the Hudson Valley

Premium Studio with Stunning Mountain & Sunset Views at The Appalachian #263

Premium Studio with Stunning Mountain & Sunset Views at The Appalachian #263
Vernon
9.8 out of 10, Exceptional, (15 reviews)
"It was all good but I think they could have the restaurant available for visitors not to many restaurants around but the stay all in all was good"
United States
Donna
The price is AU$391
includes taxes & fees
24 June - 25 June
Premium Studio with Stunning Mountain & Sunset Views at The Appalachian #263

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (53 reviews)
"Have stayed a few times now… absolutely wonderful!! Clean, cozy, and comfortable! "
United States
Daniela C.
The price is AU$349
includes taxes & fees
8 July - 9 July
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is AU$145
includes taxes & fees
19 July - 20 July
1 King Bed | Non-Smoking, Kitchen, Shower

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, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is AU$475
includes taxes & fees
24 June - 25 June
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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$421
includes taxes & fees
5 July - 6 July
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is AU$736
includes taxes & fees
28 June - 29 June
Hudson Valley Retreat w/ Pool Near Greenwood Lake

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, (34 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is AU$403
includes taxes & fees
29 June - 30 June
Cabin in the Heart of the Hudson Valley, Cabin 1
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$340 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?

Lakefront Paradise Pool + Paddle Boats Sleeps 12: This holiday home rental outside of Chester offers an outdoor pool, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your holiday with a garden and a pool table.

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.