Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

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 AU$531 per night from 13 Apr to 14 Apr
AU$531
includes taxes & fees
13 Apr - 14 Apr
When you stay at this vacation home in Fishkill, you'll be within a 10-minute drive of Northeast Regional Epilepsy Group and SplashDown Beach.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Warwick
With a stay at this vacation home in Warwick, you'll be within a 15-minute drive of LEGOLAND® New York and Lewis Woodlands.
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Stony Point
Located in Stony Point, this vacation home is within a 15-minute drive of Bear Mountain State Park and United States Military Academy.
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
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Catskills mountain gateway house.

Catskills mountain gateway house.

Bloomingburg
With a stay at this vacation home in Bloomingburg, you'll be within a 15-minute walk of Wurtsboro Ridge State Forest and Roosa Gap State Forest.
Catskills mountain gateway house.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Greenwood Lake
Located in Greenwood Lake, this vacation home is within a 5-minute drive of Greenwood Lake and Lion's Field Park.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
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
With a stay at this vacation home in New Windsor, you'll be on a river, within a 10-minute drive of United States Military Academy and Hudson River.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
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
Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!

Cornwall-On-Hudson
With a stay at this vacation home in Cornwall, you'll be in the mountains, within a 10-minute drive of United States Military Academy and New York Military ...
Bright Cornwall-On-Hudson Vacation Rental!
Spacious Westtown Home, Firepit, Up to 10 Guest

Spacious Westtown Home, Firepit, Up to 10 Guest

Westtown
Located in Westtown, this vacation home is within a 5-minute drive of High Point State Park and Minisink Heritage Museum.
Spacious Westtown Home, Firepit, Up to 10 Guest
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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
374 Holiday Homes
Lowest Price
AU$205
Highest Price
AU$531
Popular accommodation
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo, Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick, Updated Getaway w/ Pool & Hot Tub on < 3 Acres!, Catskills mountain gateway house., BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view., Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel. , Red Barn Retreat - Shawangunk Mountains Getaway, Bright Cornwall-On-Hudson Vacation Rental!, Spacious Westtown Home, Firepit, Up to 10 Guest

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 AU$205 per night from 6 Apr to 7 Apr
AU$205
includes taxes & fees
6 Apr - 7 Apr
Located in Chester, Holiday Inn Express Hotel & Suites Chester by IHG is in the business district, within a 5-minute drive of Castle Fun Center and The Rock ...
Holiday Inn Express Hotel & Suites Chester by IHG
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$214 per night from 14 Apr to 15 Apr
AU$214
includes taxes & fees
14 Apr - 15 Apr
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
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 17 Apr to 18 Apr
AU$208
includes taxes & fees
17 Apr - 18 Apr
With a stay at Sleep Inn & Suites Middletown - Goshen, you'll be centrally located in Middletown, within a 15-minute drive of LEGOLAND® New York and Paramount ...
Sleep Inn & Suites Middletown - Goshen
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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$220 per night from 27 Apr to 28 Apr
AU$220
includes taxes & fees
27 Apr - 28 Apr
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
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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.