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  1. World
  2. >North America
  3. >United States
  4. >New York
  5. >Orange
  6. >Chester

Hotels with Outdoor Pool in Chester

85 HOTELS IN AND AROUND CHESTERRanking can be influenced by the commissions we receive.
Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck main photo
Secluded 9BR Getaway, Pool, Hot Tub & Huge Deck
Villa in Chester NYUS flag
10
Excellent
$
+3
Outdoor Pool
AI-generatedThis villa boasts an outdoor pool, hot tub, and a large deck, making it ideal for large groups or families seeking a luxurious retreat. The pool area provides ample space for relaxation and entertainment.
Modern Country Retreat near Legoland w Backyard main photo
Modern Country Retreat near Legoland w Backyard
Vacation Home in Chester NYUS flag
0.0
Currently inactive on our platform.
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
18 more hotels nearby!
Pool, Fire Pit Bedroom & Alaska King Sleeps 16 main photo
Pool, Fire Pit Bedroom & Alaska King Sleeps 16
2.7 mi from Chester
Villa in Goshen NYUS flag
0.0
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Mediterranean villa hot tub fire place•fire pit main photo
Mediterranean villa hot tub fire place•fire pit
2.8 mi from Chester
Villa in Monroe NYUS flag
0.0
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
villa paraiso main photo
villa paraiso
2.9 mi from Chester
Villa in Goshen NYUS flag
10
Excellent
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Hudson Valley Retreat w/ Pool Near Greenwood Lake main photo
Hudson Valley Retreat w/ Pool Near Greenwood Lake
2.9 mi from Chester
Vacation Home in Monroe NYUS flag
9.8
Excellent
$
+2
Outdoor Pool
AI-generatedThis vacation home offers a private outdoor pool, providing a secluded and relaxing experience. The pool is a central feature for guests looking to enjoy a private swim and outdoor leisure.
Lakefront Retreat w/ Pool & Boats – Sleeps 12 main photo
Lakefront Retreat w/ Pool & Boats – Sleeps 12
3.4 mi from Chester
Vacation Home in Monroe NYUS flag
10
Excellent
$
+3
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
6BR withHeated Pool, Fire Pit & Gazebo, Sleeps 22 main photo
6BR withHeated Pool, Fire Pit & Gazebo, Sleeps 22
3.5 mi from Chester
Villa in Monroe NYUS flag
0.0
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
LEGOLAND New York Resort main photo
LEGOLAND New York Resort
3.7 mi from Chester
Hotel in Goshen NYUS flag
8.0
Very Good
$
+4
Outdoor Pool
AI-generatedThis hotel features an outdoor pool, providing a themed recreational experience for families visiting the LEGOLAND park. It combines accommodation with entertainment, making it ideal for a family vacation.
7BR Monroe Retreat, Pool, Hot Tub & Great Room main photo
7BR Monroe Retreat, Pool, Hot Tub & Great Room
4.3 mi from Chester
Villa in Monroe NYUS flag
0.0
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Decked-Out Home: Hot Tub, Pool, Fire Pit & More! main photo
Decked-Out Home: Hot Tub, Pool, Fire Pit & More!
4.3 mi from Chester
Vacation Home in Monroe NYUS flag
0.0
Currently inactive on our platform.
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Fairfield Inn & Suites Goshen Middletown main photo
Fairfield Inn & Suites Goshen Middletown
5.4 mi from Chester
Hotel in Goshen NYUS flag
8.7
Very Good
From $128
$
+6
Outdoor Pool
AI-generatedThis hotel provides an outdoor pool, perfect for guests looking to unwind and enjoy a refreshing swim. It's a comfortable option with essential amenities for a pleasant stay.
Cedar Mill Hideaway main photo
Cedar Mill Hideaway
8.0 mi from Chester
Vacation Home in Woodbury NYUS flag
9.0
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Days Inn by Wyndham Middletown main photo
Days Inn by Wyndham Middletown
8.9 mi from Chester
Hotel in New Hampton NYUS flag
5.2
Rated
From $93
$
+2
Outdoor Pool
AI-generatedThis hotel has an outdoor pool that provides guests with a place to relax and enjoy during their stay. It is a simple but welcome amenity for travelers.
Hampton Inn Middletown main photo
Hampton Inn Middletown
9.0 mi from Chester
Hotel in Middletown NYUS flag
7.6
Good
From $140
$
+7
Outdoor Pool
AI-generatedThe Hampton Inn in Middletown offers an outdoor pool for relaxation and recreation. Guests can enjoy a swim and lounge by the poolside, enhancing their stay with leisure amenities.
Cider Mill Inn Bed and Breakfast main photo
Cider Mill Inn Bed and Breakfast
11.9 mi from Chester
Bed & Breakfast in Pine Island NYUS flag
0.0
From $154
$
+7
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Buck's Homestead B&B main photo
Buck's Homestead B&B
12.5 mi from Chester
Bed & Breakfast in Montgomery NYUS flag
0.0
From $198
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Overlook Lodge and Stone Cottages at Bear Mountain main photo
Overlook Lodge and Stone Cottages at Bear Mountain
14.2 mi from Chester
Hotel in Highland Falls NYUS flag
7.9
Good
From $113
$
+8
Outdoor Pool
AI-generatedThe lodge offers an outdoor pool, allowing guests to enjoy a swim amidst the natural beauty of Bear Mountain. It provides a refreshing recreational option during warmer months.
Cozy Cabin Gateway with Pool and Firepit main photo
Cozy Cabin Gateway with Pool and Firepit
14.8 mi from Chester
Chalet in Montgomery NYUS flag
9.6
Excellent
$
+7
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Updated Getaway with Pool and Hot Tub on Less Than 3 Acres! main photo
Updated Getaway with Pool and Hot Tub on Less Than 3 Acres!
15.3 mi from Chester
Vacation Home in Stony Point NYUS flag
10
Excellent
Currently inactive on our platform.
$
+7
Info
Categories
Outdoor Pool
Pool
Heated Pool
Private Pool
Outdoor Pool
Dog Friendly
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 85 hotels in and around Chester
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