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 condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
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 WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
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 lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
32.14 km from city center
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
18.47 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

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 ...
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 ...
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
24.05 km from city center
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
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 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, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
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 business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
23.83 km from city center
Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
231 River Street North Adams MA
22.3 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 breakfast and the helpful ...
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
23.36 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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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.

Breeze Airways
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$328 Roundtrip, found 7 hours ago
$328
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $328 found 7 hours ago
Southwest Airlines
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$344 Roundtrip, found 7 hours ago
$344
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $344 found 7 hours ago
American Airlines
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$354 Roundtrip, found 7 hours ago
$354
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $354 found 7 hours ago
Delta
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$359 Roundtrip, found 7 hours ago
$359
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $359 found 7 hours ago
United
Thu, May 7 - Sun, May 10
TPA
Tampa Intl.
ALB
Albany Intl.
$369 Roundtrip, found 7 hours ago
$369
Roundtrip
found 7 hours ago
Select United flight, departing Thu, May 7 from Tampa Intl. to Albany Intl., returning Sun, May 10, priced at $369 found 7 hours ago