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  1. World
  2. >North America
  3. >United States
  4. >Vermont
  5. >Windsor
  6. >Chester

Hotels with Outdoor Pool in Chester

125 HOTELS IN AND AROUND CHESTERRanking can be influenced by the commissions we receive.
20 hotels nearby!
Hot Tub, Fire Pit & Grill: Remote Springfield Home main photo
Hot Tub, Fire Pit & Grill: Remote Springfield Home
6.3 mi from Chester
Vacation Home in Springfield VTUS flag
9.0
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Dog Friendly
Golden Stage Inn main photo
Golden Stage Inn
6.8 mi from Chester
Bed & Breakfast in Proctorsville VTUS flag
9.7
Excellent
From $253
$
+4
Outdoor Pool
AI-generatedGolden Stage Inn is a bed and breakfast with a seasonal outdoor swimming pool and a garden.
3 BR Luxury Condo at Castle Hill - 5 mi to Okemo main photo
3 BR Luxury Condo at Castle Hill - 5 mi to Okemo
7.3 mi from Chester
Apartment in Cavendish VTUS flag
0.0
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
A1 at Castle Hill main photo
A1 at Castle Hill
7.3 mi from Chester
Vacation Home in Cavendish VTUS flag
0.0
Currently inactive on our platform.
$
+4
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Ski
A1 at Castle Hill - Apartment main photo
A1 at Castle Hill - Apartment
7.3 mi from Chester
Vacation Home in Cavendish VTUS flag
7.2
Good
Currently inactive on our platform.
$
+6
Info
Categories
Outdoor Pool
Pool
Heated Pool
Indoor Pool
Outdoor Pool
Ski
Castle Hill Condos O2 main photo
Castle Hill Condos O2
7.4 mi from Chester
Apartment in Proctorsville VTUS flag
7.3
Good
From $208
$
+3
Outdoor Pool
AI-generatedThese condos are associated with Castle Hill Resort and Spa, providing access to the resort's outdoor heated pool.
The Grafton Inn main photo
The Grafton Inn
7.5 mi from Chester
Inn in Grafton VTUS flag
9.0
Excellent
From $346
$
+10
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
3 Star
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo! main photo
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
7.5 mi from Chester
Vacation Home in Proctorsville VTUS flag
9.6
Excellent
From $308
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Vermont main photo
Vermont
8.6 mi from Chester
Apartment in Ludlow VTUS flag
8.8
Excellent
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Brookhaven B7 main photo
Brookhaven B7
8.6 mi from Chester
Apartment in Ludlow VTUS flag
8.0
Very Good
From $185
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Elegant 3BR with Fireplace & Shuttle to Slopes main photo
Elegant 3BR with Fireplace & Shuttle to Slopes
8.7 mi from Chester
Vacation Home in Ludlow VTUS flag
0.0
Currently inactive on our platform.
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Ski-in/Out Townhome w/ Views at Okemo Resort! main photo
Ski-in/Out Townhome w/ Views at Okemo Resort!
9.6 mi from Chester
Vacation Home in Ludlow VTUS flag
0.0
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski In Ski Out
Blue Gentian Lodge at Magic Mountain main photo
Blue Gentian Lodge at Magic Mountain
9.6 mi from Chester
Bed & Breakfast in Londonderry VTUS flag
0.0
From $156
$
+6
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Luxe Retreat at O'Kemo's Southface Village main photo
Luxe Retreat at O'Kemo's Southface Village
9.6 mi from Chester
Apartment in Ludlow VTUS flag
0.0
Currently inactive on our platform.
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
Family Ski-In Ski-Out at South Face Village main photo
Family Ski-In Ski-Out at South Face Village
9.7 mi from Chester
Vacation Home in Ludlow VTUS flag
0.0
Currently inactive on our platform.
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Free Wi-Fi
The Upper Pass Lodge main photo
The Upper Pass Lodge
9.8 mi from Chester
Hotel in Londonderry VTUS flag
8.1
Very Good
From $93
$
+4
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Solitude Village at Okemo main photo
Solitude Village at Okemo
9.9 mi from Chester
Aparthotel in Ludlow VTUS flag
7.5
Good
From $220
$
+11
Info
Categories
Outdoor Pool
Pool
Indoor Pool
Outdoor Pool
Ski In Ski Out
Okemo Mountain Vista main photo
Okemo Mountain Vista
10.1 mi from Chester
Apartment in Ludlow VTUS flag
0.0
From $853
$
+5
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski
Okemo Trailside 08E main photo
Okemo Trailside 08E
10.2 mi from Chester
Apartments in Ludlow VTUS flag
4.9
Rated
From $138
$
+6
Info
Categories
Outdoor Pool
Pool
Heated Pool
Outdoor Pool
Ski
Trailside 19BU & 19BL main photo
Trailside 19BU & 19BL
10.3 mi from Chester
Apartment in Ludlow VTUS flag
0.0
From $603
$
+6
Info
Categories
Outdoor Pool
Pool
Outdoor Pool
Ski In Ski Out
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 125 hotels in and around Chester
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