Rent a castle in Chester, NY

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Chester, NY

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Popular castles

Stunning Country Tudor Estate of Bygone Era

Goshen, NY

30 guests

From 
$500
/hr
10 hr min

Chateau Castle one hour from New York City!

Warwick, NY

5.0 (9)

30 guests

From 
$250
/hr
4 hr min

Private Country Retreat with Pool, Hot Tub & Entertainment Spaces

Chester, NY

30 guests

From 
$175
/hr
1 hr min

Mountain View Villa

Woodbury, Highland Mills, NY

5.0 (1)

20 guests

From 
$250
/hr
4 hr min

Rustic 1700's Farmhouse with Recording Studio 1hr from NYC

Warwick, NY

20 guests

From 
$250
/hr
2 hr min

Modern Rustic-Luxe home with pool, pond, barns and gardens on 6 acres

Warwick, NY

100 guests

From 
$200
/hr
1 hr min

Historic Victorian Farm House

Warwick, NY

25 guests

From 
$500
/hr
2 hr min

Chic lakeside estate

Hewitt, West Milford, NJ

300 guests

From 
$500
/hr
3 hr min

Private 4+ Acre Photo & Film Estate | Stone Cellar, Bar & Grounds

Warwick, NY

15 guests

From 
$150
/hr
2 hr min

A Modern Cabin in Middletown

Wallkill, Middletown, NY

15 guests

From 
$200
/hr
5 hr min

Beautiful A Fram Cabin in NY

Montgomery, NY

5.0 (5)

20 guests

From 
$100
/hr
2 hr min

1850s Riverfront Carpenter Victorian 2 acres

Cornwall-on-hudson, NY

75 guests

From 
$200
/hr
12 hr min

Upstate NY Luxury Estate with Pool, Padel Court & Scenic Views

Minisink, New York, NY

20 guests

From 
$300
/hr
4 hr min

Quiet cottage

Cornwall, Cornwall On Hudson, NY

15 guests

From 
$150
/hr
3 hr min

Historic Airstream in Countryside Setting with Rustic Barn

Wesley Hills, Suffern, NY

30 guests

From 
$400
/hr
4 hr min

Hudson Valley Mansion with Hudson River Views in Historic City of Newburgh.

Newburgh, NY

30 guests

From 
$250
/hr
6 hr min

1869 Second Empire Victorian on 1 Acre with Carriage House

Cold Spring, NY

100 guests

From 
$400
/hr
4 hr min

Stunning historic Victorian house in Newburgh, NY

Newburgh, NY

5.0 (1)

10 guests

From 
$200
/hr
1 hr min

Mid-Century Modern Designer Home with Hudson Valley Views

Newburgh, NY

4.0 (1)

50 guests

From 
$390
/hr
4 hr min

Mid Century modern country house situated on a brook on over 5 secluded, wooded acres in the Hudson Valley, including 2 acres of curated botanical gardens

Philipstown, Garrison, NY

25 guests

From 
$850
/hr
4 hr min

Italianate Victorian Home

Peekskill, NY

5.0 (2)

20 guests

From 
$300
/hr
6 hr min

Modern Design Loft in Beacon + Hudson River Valley

Beacon, NY

5.0 (2)

20 guests

From 
$300
/hr
12 hr min

Ultra Modern Private Oasis with River Views

Newburgh, NY

10 guests

From 
$99
/hr
3 hr min

Upstate Mid Century Modern A-frame Mountain Chalet - Spacious, 2 levels, access to yard and balcony

Beacon, NY

30 guests

From 
$275
/hr
4 hr min

Hudson Valley Escape With Stunning View and Hot Tub

Newburgh, NY

5.0 (1)

20 guests

From 
$350
/hr
4 hr min

Unique Castle Home | 5224

Lake Peekskill, NY

30 guests

From 
$425
/hr
8 hr min

The White House in the Mountains.

Mamakating, Wurtsboro, NY

300 guests

From 
$100
/hr
6 hr min

Renovated Gothic Farmhouse in New York’s Hudson Valley

Wappinger, Wappingers Falls, NY

50 guests

From 
$400
/hr
4 hr min

Similar searches in Chester, NY

Updated October 25, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.