Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor
When you stay at this vacation home in New Windsor, you'll be on a river, within a 5-minute drive of Hudson River and Delano-Hitch Recreation Park.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
The Perfect up to date Private Getaway to call home for a while

The Perfect up to date Private Getaway to call home for a while

Bloomingburg
Located in Bloomingburg, this vacation home is in the mountains, a 3-minute drive from Bloomingburg Village Hall and 6 minutes from Wurtsboro Ridge State ...
The Perfect up to date Private Getaway to call home for a while
Greenwoods of Warwick

Greenwoods of Warwick

Monroe
With a stay at this vacation home in Monroe, you'll be within a 5-minute drive of Greenwood Lake and Sterling Forest State Park.
Greenwoods of Warwick
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Elegant and spacious home with sauna and heated pool

Elegant and spacious home with sauna and heated pool

Monroe
With a stay at this vacation home in Monroe, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and Schunnemunk State Park.
Elegant and spacious home with sauna and heated pool
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 AU$528 per night from 6 Jan to 7 Jan
AU$528
includes taxes & fees
6 Jan - 7 Jan 2025
With a stay at this vacation home in Vernon, you'll be in the mountains, within a 10-minute drive of Crystal Springs Golf Resort and Mountain Creek Ski ...
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
 Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

wallkill
The price is AU$591 per night from 5 Jan to 6 Jan
AU$591
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Wallkill, this vacation home is on the waterfront, within a 15-minute drive of Angry Orchard and Tuthilltown Spirits.
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Pine Bush
The price is AU$977 per night from 23 Jan to 24 Jan
AU$977
includes taxes & fees
23 Jan - 24 Jan 2025
Located in Pine Bush, this vacation home is in the mountains, within a 10-minute drive of Brimstone Hill Winery and Minnewaska State Park.
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Spectacular ~10k sqft Mansion w/Pool&Tennis

Spectacular ~10k sqft Mansion w/Pool&Tennis

Goshen
The price is AU$4,879 per night from 25 Dec to 26 Dec
AU$4,879
includes taxes & fees
25 Dec - 26 Dec
When you stay at this vacation home in Goshen, you'll be in the mountains, within a 15-minute drive of LEGOLAND® New York and Woodbury Common Premium ...
Spectacular ~10k sqft Mansion w/Pool&Tennis
By Mtn Creek Resort: ‘The Point on Highland Lake’

By Mtn Creek Resort: ‘The Point on Highland Lake’

Highland Lakes
With a stay at this vacation home in Highland Lakes, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 11 minutes by foot from Upper East ...
By Mtn Creek Resort: ‘The Point on Highland Lake’
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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
302 Holiday Homes
Lowest Price
AU$176
Highest Price
AU$4,879
Popular accommodation
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel. , The Perfect up to date Private Getaway to call home for a while, Greenwoods of Warwick, Elegant and spacious home with sauna and heated pool, Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out, Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!, Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park, Spectacular ~10k sqft Mansion w/Pool&Tennis, By Mtn Creek Resort: ‘The Point on Highland Lake’

Top trending hotels in Chester

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

2.5 out of 5
2 Bryle Place, Chester, NY
Fully refundable
The price is AU$176 per night from 1 Jan to 2 Jan
AU$176
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Chester, Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is in the business district, within a 5-minute drive of Castle Fun Center and The ...
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59, Nanuet, NY
Fully refundableReserve now, pay when you stay
The price is AU$211 per night from 19 Jan to 20 Jan
AU$211
includes taxes & fees
19 Jan - 20 Jan 2025
Located in Nanuet, DoubleTree by Hilton Hotel Nanuet is in a shopping district, within a 10-minute drive of Palisades Center and Rockland Lake State Park.
DoubleTree by Hilton Hotel Nanuet
Crowne Plaza Suffern - Mahwah, an IHG Hotel

Crowne Plaza Suffern - Mahwah, an IHG Hotel

3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundable
The price is AU$227 per night from 29 Dec to 30 Dec
AU$227
includes taxes & fees
29 Dec - 30 Dec
Located in Suffern, Crowne Plaza Suffern - Mahwah, an IHG Hotel is in the suburbs, a 4-minute drive from Rockland Community College and 6 minutes from Ramapo ...
Crowne Plaza Suffern - Mahwah, an IHG Hotel
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HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 1 Jan to 2 Jan
AU$178
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Fishkill, HYATT house Fishkill/Poughkeepsie is a 4-minute drive from SplashDown Beach and 10 minutes from Dia Beacon.
HYATT house Fishkill/Poughkeepsie
Don't see what you're looking for?
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.