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 ...
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 ...
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 ...
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 ...
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. ...
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. ...
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 ...
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 ...
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 ...
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 ...
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. ...
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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.

United
Wed, Dec 24 - Wed, Dec 31
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$441 Roundtrip, found 18 hours ago
$441
Roundtrip
found 18 hours ago
Select United flight, departing Wed, Dec 24 from Sky Harbor Intl. to Albany Intl., returning Wed, Dec 31, priced at $441 found 18 hours ago
Delta
Wed, Dec 24 - Thu, Dec 25
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$490 Roundtrip, found 18 hours ago
$490
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Dec 24 from Sky Harbor Intl. to Albany Intl., returning Thu, Dec 25, priced at $490 found 18 hours ago
JetBlue Airways
Wed, Dec 24 - Mon, Dec 29
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$670 Roundtrip, found 18 hours ago
$670
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Wed, Dec 24 from Sky Harbor Intl. to Albany Intl., returning Mon, Dec 29, priced at $670 found 18 hours ago
American Airlines
Thu, Dec 25 - Fri, Dec 26
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$760 Roundtrip, found 18 hours ago
$760
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Thu, Dec 25 from Sky Harbor Intl. to Albany Intl., returning Fri, Dec 26, priced at $760 found 18 hours ago