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$528 per night from 23 Apr to 24 Apr
AU$528
includes taxes & fees
23 Apr - 24 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$204
Highest Price
AU$528
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
The price is AU$253 per night from 4 May to 5 May
AU$253
includes taxes & fees
4 May - 5 May
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
The price is AU$204 per night from 29 Apr to 30 Apr
AU$204
includes taxes & fees
29 Apr - 30 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
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 27 Apr to 28 Apr
AU$233
includes taxes & fees
27 Apr - 28 Apr
With a stay at La Quinta Inn & Suites by Wyndham Middletown-Goshen in Middletown, you'll be in a shopping district, within a 15-minute drive of LEGOLAND® New ...
La Quinta Inn & Suites by Wyndham Middletown
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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$229 per night from 20 May to 21 May
AU$229
includes taxes & fees
20 May - 21 May
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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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.