Glendale Hotel Guide - Hotels with Pool in Glendale, Massachusetts

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Check availability on Glendale Hotels with Pool

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Glendale Hotels with Pool

Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed
The Old Inn On The Green

The Old Inn On The Green

4.0 star property
Great Barrington
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.2 out of 10, Wonderful, (90)
Refreshing waters beckon from the seasonal outdoor pool, open May through August amid lush garden grounds. After swimming, guests savour fantastic meals at the acclaimed on-site American restaurant, which offers breakfast, lunch, and dinner in an upscale setting.
The price is €317
includes taxes & fees
2 Dec - 3 Dec
The Old Inn On The Green
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
  • Near the beach
7.6 out of 10, Good, (410)
Mountain recreation surrounds this quiet getaway featuring a refreshing seasonal pool open from August. After swimming, guests appreciate clean, comfortable rooms with mini fridges before exploring nearby skiing and hiking trails.
The price is €87
includes taxes & fees
2 Dec - 3 Dec
Sunset Inn
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (827)
Sparkling waters beckon at the inviting outdoor pool, a refreshing retreat after exploring nearby Tanglewood Music Centre. Deep soaking bathtubs and hydromassage showers in clean, spacious rooms complement this conveniently located getaway.
The price is €76
includes taxes & fees
2 Dec - 3 Dec
Howard Johnson by Wyndham Lenox
Outdoor pool
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
  • Outdoor pool
  • Poolside bar
9.4 out of 10, Exceptional, (163)
Poolside cocktails enhance summer swims at this tranquil Berkshires retreat. Guests savour exceptional made-to-order breakfasts before relaxing in spacious, fireplace-equipped rooms. Nearby Tanglewood and hiking trails complete perfect seasonal getaways.
Brook Farm Inn
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
  • Pool loungers
9.2 out of 10, Wonderful, (110)
Seasonal swimming awaits at this luxury bed & breakfast, where summer days unfold between pool loungers and excellent breakfasts. Adventure seekers can enjoy kayaking, mountain biking, and horseback riding before returning to individually furnished rooms.
The price is €398
includes taxes & fees
14 Dec - 15 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Outdoor pool, pool loungers
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
  • Outdoor pool
  • Pool loungers
10.0 out of 10, Exceptional, (134)
Surrounded by loungers for sun-soaked relaxation, the serene outdoor pool creates a perfect countryside escape. Guests savour complimentary gourmet breakfasts before exploring nearby hiking trails or enjoying a therapeutic massage at this charming B&B.
Devonfield Inn B&B
Seasonal outdoor pool
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
7.8 out of 10, Good, (839)
Seasonal outdoor pool beckons sun-seekers from June through August at this spotless, centrally located motel. After a day of skiing or city centre exploration, guests appreciate comfortable beds, updated rooms with refrigerators, and friendly service.
The price is €83
includes taxes & fees
2 Dec - 3 Dec
Berkshire Inn
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
  • Pool loungers
9.6 out of 10, Exceptional, (15)
Mountain adventures begin at the outdoor pool, complete with sun loungers and umbrellas for post-hike relaxation. Sauna sessions, complimentary bicycles, and nearby hiking trails complement the experience at this scenic Berkshire retreat.
The price is €279
includes taxes & fees
17 Dec - 18 Dec
Prospect Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
  • Outdoor pool
  • Indoor pool
  • Pool loungers
  • Hot tub
8.6 out of 10, Excellent, (134)
Swimmers glide through crystal waters at indoor and outdoor pools surrounded by serene Berkshire landscapes. Beyond aquatic pleasures, this resort boasts tennis courts, a sauna, and spacious accommodation with cosy fireplaces and full kitchens.
The Ponds at Foxhollow
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
Great Barrington
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • Extra beds/cots
8.6 out of 10, Excellent, (547)
Aquatic adventures beckon with access to a nearby outdoor pool, complementing garden strolls at this cosy Berkshire motel. Nestled close to Norman Rockwell Museum and Ski Butternut, guests praise the helpful staff and comfortable accommodation.
The price is €106
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
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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Top Glendale Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Love this place! Great rooms, view of the lake, Indian restaurant inside, and wonderful breakfast choices. We’ll be back. "
Keville 1-night trip
Posted 6 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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Frequently asked questions

What are some accommodation options with pools in Glendale?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. The Red Lion Inn: Provides 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Provides a seasonal outdoor pool, an indoor pool and buffet.
What is there to see and do in Glendale?
Spend some time experiencing the great outdoors at Housatonic River. Discover sights such as Norman Rockwell Museum, Naumkeag Museum and National Shrine of the Divine Mercy during your stay.