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Hotels with Swimming Pool near Ski Resorts in Chester

57 HOTELS IN AND AROUND CHESTERRanking can be influenced by the commissions we receive.
20 hotels nearby!
Rustic-Chic Home with Decks Pool and Lake Access main photo
Rustic-Chic Home with Decks Pool and Lake Access
9.3 km from Chester
Vacation Home in Otis MAUS flag
0.0
$
Info
Categories
Ski
Pool
Serene Berkshires Oasis with Pool and Sculpture Garden main photo
Serene Berkshires Oasis with Pool and Sculpture Garden
11.5 km from Chester
Vacation Home in Otis MAUS flag
0.0
$
Info
Categories
Ski
Pool
Private Pool
Outdoor Pool
Monterey Home with Hot Tub, Pool and Game Room! main photo
Monterey Home with Hot Tub, Pool and Game Room!
13.7 km from Chester
Vacation Home in Monterey MAUS flag
0.0
$
Info
Categories
Ski
Pool
Private Pool
Outdoor Pool
Applegate Inn main photo
Applegate Inn
14.7 km from Chester
Bed & Breakfast in Lee MAUS flag
0.0
From $40
$
Info
Categories
Ski
Pool
Heated Pool
Outdoor Pool
Parking
EV charging stations
Devonfield Inn main photo
Devonfield Inn
15.0 km from Chester
Bed & Breakfast in Lee MAUS flag
8.4
Very Good
From $363
$
Info
Categories
Ski
Pool
Heated Pool
Outdoor Pool
Small
Country Charmer main photo
Country Charmer
15.1 km from Chester
Vacation Home in Lee MAUS flag
0.0
$
Info
Categories
Ski
Pool
Private Pool
Outdoor Pool
Dog Friendly
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires main photo
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires
15.4 km from Chester
Hotel in South Lee MAUS flag
8.9
Excellent
From $136
$
Info
Summary of reviews
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires offers an idyllic escape nestled amidst the scenic beauty of the Berkshires. Known for its prime location, the resort is a favorite among nature lovers and families, providing convenient access to nearby hiking trails, ski resorts, and charming towns such as Stockbridge. Visitors laud the resort’s tranquil and scenic setting, which is complemented by a host of family-friendly amenities.

The accommodations stand out for their exceptional spaciousness and comfort. Guests appreciate the thoughtfully designed villa options that cater to families, featuring multiple bedrooms, full kitchens, and distinct areas for relaxation, making for an inviting and home-like ambiance. The emphasis on cleanliness further enhances the experience, with rooms described as spotless and well-maintained. The resort staff consistently receives praise for their friendliness and helpfulness, contributing to a warm and welcoming atmosphere that guests greatly appreciate.

The resort’s pool facilities, both indoor and outdoor, provide ample enjoyment and relaxation opportunities, especially noted for their cleanliness and convenience. Families find the pools, along with additional amenities such as mini-golf and an arcade, particularly engaging for children of all ages. Moreover, ski enthusiasts find the location ideal, with easy access to popular ski destinations like Otis Ski Ridge and Jiminy Peak.

While there are some limitations regarding dining options on-site, the full kitchens in the villas allow guests the flexibility to prepare their own meals. Beds are frequently highlighted for their comfort, ensuring restful nights. Overall, the resort effectively surpasses its three-star rating, offering a satisfying blend of comfort, convenience, and a picturesque setting, making it a preferred choice for families and adventurers seeking a memorable getaway in the Berkshires.
Categories
Pool
Heated Pool
Indoor Pool
Outdoor Pool
Ski
Family
Cranwell Spa and Golf Resort main photo
Cranwell Spa and Golf Resort
15.7 km from Chester
Resort in Lenox MAUS flag
8.1
Very Good
$
Info
Categories
Ski
Pool
Pool Lap Lanes
Golf
Hampton Inn Westfield main photo
Hampton Inn Westfield
15.7 km from Chester
Hotel in Westfield MAUS flag
7.8
Good
From $153
$
Info
Categories
Ski
Pool
Indoor Pool
Free Wi-Fi
Eastover Estate and Eco Village main photo
Eastover Estate and Eco Village
15.8 km from Chester
Resort in Lenox MAUS flag
5.4
Rated
From $1,005
$
Info
Categories
Ski
Pool
Pool Lap Lanes
Family
Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing main photo
$
Info
Categories
Ski
Pool
Private Pool
Outdoor Pool
The Ponds at Foxhollow main photo
The Ponds at Foxhollow
15.9 km from Chester
Resort in Lenox MAUS flag
8.3
Very Good
From $112
$
Info
Categories
Ski
Pool
Indoor Pool
Outdoor Pool
Golf
Seven Hills Inn main photo
Seven Hills Inn
16.2 km from Chester
Inn in Lenox MAUS flag
7.3
Good
From $166
$
Info
Categories
Ski
Pool
Heated Pool
Outdoor Pool
Dog Friendly
Lenox House with Screened Patio and Mountain View main photo
Lenox House with Screened Patio and Mountain View
16.4 km from Chester
Vacation Home in Lenox MAUS flag
0.0
$
Info
Categories
Ski
Pool
Outdoor Pool
Dog Friendly
Rockspring by AvantStay Huge Berkshires Estate main photo
Rockspring by AvantStay Huge Berkshires Estate
16.5 km from Chester
Vacation Home in Stockbridge MAUS flag
0.0
$
Info
Categories
Ski
Pool
Private Pool
Outdoor Pool
Dog Friendly
Hampton Terrace Inn main photo
Hampton Terrace Inn
16.6 km from Chester
Hotel in Lenox MAUS flag
9.2
Excellent
From $306
$
Info
Categories
Ski
Pool
Heated Pool
Outdoor Pool
Honeymoon
The Inn at Stockbridge main photo
The Inn at Stockbridge
16.6 km from Chester
Bed & Breakfast in Stockbridge MAUS flag
9.5
Excellent
From $425
$
Info
Categories
Ski
Pool
Dog Friendly
Garden Gables Inn main photo
Garden Gables Inn
16.8 km from Chester
Guest House in Lenox MAUS flag
0.0
From $87
$
Info
Categories
Ski
Pool
Outdoor Pool
Free Wi-Fi
Brook Farm Inn main photo
Brook Farm Inn
16.9 km from Chester
Bed & Breakfast in Lenox MAUS flag
9.0
Excellent
From $217
$
Info
Categories
Ski
Pool
Heated Pool
Outdoor Pool
Accessible
Days Inn by Wyndham Lenox MA main photo
Days Inn by Wyndham Lenox MA
17.0 km from Chester
Hotel in Lenox MAUS flag
7.1
Good
From $136
$
Info
Categories
Ski
Pool
Outdoor Pool
Family
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 57 hotels in and around Chester
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