Downtown Great Barrington Vacation Packages for 2026
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Downtown Great Barrington Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Latham/Albany Airport
$841
per person
Dec 19 - Dec 27
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly motel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.
The Landing Hotel at Rivers Casino Schenectady
Nothside
$1,402
per person
Dec 19 - Dec 27
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Schenectady Light Opera Performing Arts Center are located nearby.
Country Inn & Suites by Radisson, Downtown Albany New York
Downtown Albany
$859
per person
Dec 19 - Dec 27
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Popular attractions MVP Arena and Colonie Center Mall are located nearby.
Excellent stay.
Reviewed on Oct 15, 2026
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
$937
per person
Dec 19 - Dec 27
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Clifton Park. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Regal Clifton Park and Wicked Eatery Pub & Entertainment are located nearby.
It was clean, dark, quiet and had a comfy bed.
Reviewed on Oct 15, 2026
Marriott Albany
$1,076
per person
Dec 19 - Dec 27
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy an outdoor pool, a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Colonie Center Mall and MVP Arena are located nearby.
Clean rooms that seem renovated recently.
Reviewed on Oct 15, 2026
The Clocktower Hotel Latham - North Albany, an Ascend Collection Hotel
$912
per person
Dec 19 - Dec 27
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Cohoes. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.
Great stay overall. Staff was friendly and helpful.
It is a bit hard to find the hotel from the road as the sign is hidden.
Pool was great.
Had one issue when we got back late and both keycards did not work. Was not happy about this as we were trying to keep two kids asleep.
Overall, great stay. Would probably stay here again.
Reviewed on Oct 15, 2026
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See all available trips from Columbus to Downtown Great Barrington
View all tripsTop Hotel Deals
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
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
461 Pittsfield Rd Lenox MA
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
194 Pittsfield Rd Lenox MA
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
190 Meadow Street South Lee MA
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
30 Main Street Stockbridge MA
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
297 North Street Pittsfield MA
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 ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
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 ...
Prospect Berkshires
50 Prospect Lake Rd Egremont MA
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
The Whitlock
16 Church St Lenox MA
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 ...
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
The Cornell Inn, Lenox & The Berkshires
203 Main St Lenox MA
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 ...
Interlaken Inn & Resort
74 Interlaken Road Lakeville CT
Book a stay at this spa hotel in Lakeville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Holley-Williams House Museum and Gay Woods ...
Courtyard by Marriott Lenox Berkshires
70 Pittsfield Rd Lenox MA
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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See all available properties in Downtown Great Barrington
View all propertiesLowest 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.
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$332
Roundtrip
found 6 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$332
Roundtrip
found 6 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$332
Roundtrip
found 6 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$332
Roundtrip
found 6 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$357
Roundtrip
found 6 days ago
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