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
21.86 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 ...
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 ...
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. ...
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 ...
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. ...
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 ...
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 ...
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 ...
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. ...
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
21.76 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 helpful staff ...
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.

American Airlines
Sat, Jan 17 - Sat, Jan 31
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jan 17 from Charlotte-Douglas Intl. to Albany Intl., returning Sat, Jan 31, priced at $189 found 5 days ago
Delta
Wed, Nov 18 - Thu, Nov 19
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Nov 19, priced at $217 found 4 days ago
United
Wed, Nov 18 - Thu, Nov 19
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$247 Roundtrip, found 4 days ago
$247
Roundtrip
found 4 days ago
Select United flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Nov 19, priced at $247 found 4 days ago
JetBlue Airways
Tue, Jun 9 - Fri, Jun 12
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jun 9 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Fri, Jun 12, priced at $257 found 6 days ago
Southwest Airlines
Sat, Jan 17 - Sat, Jan 31
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Charlotte-Douglas Intl. to Albany Intl., returning Sat, Jan 31, priced at $279 found 5 days ago