Chester Holiday Homes

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Featured Holiday Homes in Chester

Beautiful Private Stone Home in the Hudson Valley

Beautiful Private Stone Home in the Hudson Valley

Pine Bush
Located in Pine Bush, this vacation home is within a 10-minute drive of Lake Awosting Beach and Minnewaska State Park.
Beautiful Private Stone Home in the Hudson Valley
Red Barn Retreat - Shawangunk Mountains Getaway

Red Barn Retreat - Shawangunk Mountains Getaway

Gardiner
When you stay at this vacation home in Gardiner, you'll be on the waterfront, within a 5-minute drive of Whitecliff Vineyard and DM Weil Gallery.
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]

complete privacy vacation home [private pool]

Newburgh
The price is AU$1,708 per night from 3 Nov to 4 Nov
AU$1,708
includes taxes & fees
3 Nov - 4 Nov
Located in Newburgh, this vacation home is within a 10-minute drive of Chadwick Lake Park and Mount Saint Mary's College Newburgh.
complete privacy vacation home [private pool]
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Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Monroe
The price is AU$2,000 per night from 4 Nov to 5 Nov
AU$2,000
includes taxes & fees
4 Nov - 5 Nov
Located in Monroe, this vacation home is within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
 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$578 per night from 7 Nov to 8 Nov
AU$578
includes taxes & fees
7 Nov - 8 Nov
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!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

Garrison
Located in Philipstown, this vacation home is in the mountains, a 4-minute drive from Graymoor - The Holy Mountain and 9 minutes from Peekskill Landing ...
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Nature Getaway: Charming Villa Near Trails and Parks

Nature Getaway: Charming Villa Near Trails and Parks

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.
Nature Getaway: Charming Villa Near Trails and Parks
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Pine Bush
Located in Pine Bush, this vacation home is on a river, within a 15-minute drive of Brimstone Hill Winery and Angry Orchard.
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake

Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake

Greenwood Lake
When you a stay at this vacation home in Greenwood Lake, you'll be in the mountains, just steps from Greenwood Lake and Lion's Field Park.
Lakeview with Mountain View, Nature seeker friendly. Greenwood 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
286 Holiday Homes
Lowest Price
AU$173
Highest Price
AU$2,000
Popular accommodation
Beautiful Private Stone Home in the Hudson Valley, Red Barn Retreat - Shawangunk Mountains Getaway, complete privacy vacation home [private pool], Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!, Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!, 'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, Nature Getaway: Charming Villa Near Trails and Parks, Pet-Friendly ‘Pond View Loft' w/ Private Pool!, Lakeview with Mountain View, Nature seeker friendly. Greenwood 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$185 per night from 2 Dec to 3 Dec
AU$185
includes taxes & fees
2 Dec - 3 Dec
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$186 per night from 3 Dec to 4 Dec
AU$186
includes taxes & fees
3 Dec - 4 Dec
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
Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites

3.5 out of 5
14 Schuyler Blvd, Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 24 Nov to 25 Nov
AU$173
includes taxes & fees
24 Nov - 25 Nov
With a stay at Best Western Fishkill Inn & Suites in Fishkill, you'll be 5.1 mi (8.2 km) from Hudson Valley Research Park and 12.2 mi (19.6 km) from Vassar ...
Best Western Fishkill Inn & Suites
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Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is AU$200 per night from 5 Nov to 6 Nov
AU$200
includes taxes & fees
5 Nov - 6 Nov
When you stay at Overlook Lodge at Bear Mountain in Bear Mountain, you'll be in a state park, a 1-minute drive from Bear Mountain State Park and 7 minutes from ...
Overlook Lodge at Bear Mountain
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.