Chatham 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
33.49 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 ...
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
31.65 km from city center
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
27.73 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 ...
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
32.39 km from city center
Book a stay at this business-friendly hotel in Glenmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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
28.28 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 ...
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
549 Washington Street Hudson NY
19.92 km from city center
Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
29.4 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 ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
26.52 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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
27.24 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 ...
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
3 Mount Hope Way Albany NY
32.98 km from city center
Book a stay at this business-friendly hotel in Albany. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
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
24.51 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 ...
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 out of 5
99 Miller Rd Castleton-on-Hudson NY
24.95 km from city center
Book a stay at this business-friendly hotel in Castleton-on-Hudson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
24.99 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
29.75 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 ...
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
26.52 km from city center
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
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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, Jun 27 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$333 Roundtrip, found 13 hours ago
$333
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Jun 27 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sat, Jul 4, priced at $333 found 13 hours ago
Delta
Sat, Jun 27 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$339 Roundtrip, found 13 hours ago
$339
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Jun 27 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sat, Jul 4, priced at $339 found 13 hours ago
United
Tue, May 19 - Wed, May 27
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$379 Roundtrip, found 1 day ago
$379
Roundtrip
found 1 day ago
Select United flight, departing Tue, May 19 from Charlotte-Douglas Intl. to Albany Intl., returning Wed, May 27, priced at $379 found 1 day ago
Southwest Airlines
Fri, May 22 - Wed, May 27
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$383 Roundtrip, found 1 day ago
$383
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, May 22 from Charlotte-Douglas Intl. to Albany Intl., returning Wed, May 27, priced at $383 found 1 day ago
JetBlue Airways
Wed, May 13 - Tue, May 19
SFO
San Francisco Intl.
ALB
Albany Intl.
$390 Roundtrip, found 2 days ago
$390
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, May 13 from San Francisco Intl. to Albany Intl., returning Tue, May 19, priced at $390 found 2 days ago