Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

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
The price is NZ$537 per night from 11 Nov to 12 Nov
NZ$537
11 Nov - 12 Nov
includes taxes & fees
Book a stay at this ski vacation home in Vernon. Enjoy free WiFi, ski-in/ski-out access, and balconies. Popular attractions Mountain Creek Waterpark and Crystal ...
Opens in a new windowMountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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
The price is NZ$585 per night from 30 Nov to 1 Dec
NZ$585
30 Nov - 1 Dec
includes taxes & fees
Stay at this vacation home in Fishkill. Enjoy a garden, laundry facilities, and patios. Popular attractions SplashDown Beach and Van Wyck Homestead Museum are ...
Opens in a new windowLarge Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Chestnut on Willow Lake

Chestnut on Willow Lake

Fishkill
The price is NZ$1,114 per night from 6 Nov to 7 Nov
NZ$1,114
6 Nov - 7 Nov
includes taxes & fees
Stay at this vacation home in Fishkill. Enjoy laundry facilities. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course are located nearby.
Opens in a new windowChestnut on Willow Lake
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Hickory on Willow Lake

Hickory on Willow Lake

Fishkill
The price is NZ$1,184 per night from 10 Nov to 11 Nov
NZ$1,184
10 Nov - 11 Nov
includes taxes & fees
Stay at this vacation home in Fishkill. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Van Wyck Homestead Museum and ...
Opens in a new windowHickory on Willow Lake
The Woodbury Cottage

The Woodbury Cottage

Woodbury
Stay at this vacation home in Woodbury. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Woodbury Common Premium Outlets ...
Opens in a new windowThe Woodbury Cottage
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

2 out of 5
Vernon
Stay at this vacation home in Sussex. Enjoy free WiFi, private pools, and a garden. Popular attractions Mountain Creek Waterpark and Crystal Springs Golf Resort ...
Opens in a new windowLuxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries
 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
The price is NZ$259 per night from 9 Nov to 10 Nov
NZ$259
9 Nov - 10 Nov
includes taxes & fees
Stay at this vacation home in Warwick. Enjoy air conditioning. Popular attractions Railroad Green and Strazza Art Gallery are located nearby.
Opens in a new window Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Greenwood Lake Lakefront Luxury

Greenwood Lake Lakefront Luxury

Hewitt
Stay at this vacation home in West Milford. Enjoy laundry facilities, patios, and cable/satellite TV service. Our guests praise the property condition in our ...
Opens in a new windowGreenwood Lake Lakefront Luxury
Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Greenwood Lake
Stay at this vacation home in Greenwood Lake. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Lion's Field Park and ...
Opens in a new windowCharming 2-bedroom house in Greenwood Lake with Central AC/Heat
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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.

Chester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chester Holiday Homes essential information

Accommodation
327 Holiday Homes
Lowest Price
NZ$203
Highest Price
NZ$1,184
Popular accommodation
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out, Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo, Chestnut on Willow Lake, Hickory on Willow Lake, The Woodbury Cottage, Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries, Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town, Greenwood Lake Lakefront Luxury, Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Top trending hotels in Chester

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place, Chester, NY
Fully refundable
The price is NZ$203 per night from 6 Nov to 7 Nov
NZ$203
6 Nov - 7 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowHoliday Inn Express Hotel & Suites Chester by IHG
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2.5 out of 5
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
The price is NZ$220 per night from 18 Nov to 19 Nov
NZ$220
18 Nov - 19 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Nanuet. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
Opens in a new windowSonesta Simply Suites Nanuet
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is NZ$203 per night from 10 Nov to 11 Nov
NZ$203
10 Nov - 11 Nov
includes taxes & fees
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowThe Crossroads Hotel, Newburgh
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Hampton Inn Nanuet

Hampton Inn Nanuet

2.5 out of 5
260 W Route 59, Nanuet, NY
The price is NZ$209 per night from 11 Nov to 12 Nov
NZ$209
11 Nov - 12 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Nanuet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowHampton Inn Nanuet
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See all available properties in Chester
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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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^Subject to availability and chosen travel dates.