Windsor Vacations

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Top Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
20.99 km from city center
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
20.85 km from city center
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
21.65 km from city center
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

3.5 out of 5
190 Meadow Street South Lee MA
31.99 km from city center
Book a stay at this ski hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
33.37 km from city center
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
18.1 km from city center
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
23.14 km from city center
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
21.11 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
21.82 km from city center
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
27.28 km from city center
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
25.83 km from city center
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
35.49 km from city center
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
13.62 km from city center
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
The Whitlock

The Whitlock

2 out of 5
16 Church St Lenox MA
25.8 km from city center
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
203 Main St Lenox MA
25.06 km from city center
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Dec 5 - Tue, Dec 15
TPA
Tampa Intl.
ALB
Albany Intl.
$347 Roundtrip, found 2 days ago
$347
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Dec 5 from Tampa Intl. to Albany Intl., returning Tue, Dec 15, priced at $347 found 2 days ago
American Airlines
Sat, Dec 5 - Tue, Dec 15
TPA
Tampa Intl.
ALB
Albany Intl.
$357 Roundtrip, found 2 days ago
$357
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Dec 5 from Tampa Intl. to Albany Intl., returning Tue, Dec 15, priced at $357 found 2 days ago
United
Sat, Dec 5 - Tue, Dec 15
TPA
Tampa Intl.
ALB
Albany Intl.
$357 Roundtrip, found 2 days ago
$357
Roundtrip
found 2 days ago
Select United flight, departing Sat, Dec 5 from Tampa Intl. to Albany Intl., returning Tue, Dec 15, priced at $357 found 2 days ago
Delta
Sat, Dec 5 - Mon, Dec 7
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$407 Roundtrip, found 3 days ago
$407
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Dec 5 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Mon, Dec 7, priced at $407 found 3 days ago
JetBlue Airways
Wed, Dec 2 - Wed, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$413 Roundtrip, found 3 days ago
$413
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Wed, Dec 9, priced at $413 found 3 days ago