Great Barrington Vacations
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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 10 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 10 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 10 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 10 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 10 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 10 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 Great Barrington
View all tripsGreat Barrington Vacation Packages
Trying to plan a way to package your Great Barrington flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Great Barrington incredible. In only a few clicks, you can select the best Great Barrington vacation package for you and your family. We have a huge choice of flights and hotels, and Great Barrington things to do to select from.
Hotel Deals in Great Barrington
You can choose from around 1603 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Great Barrington hot spots, we have plenty of options available.
We have great deals on everything from luxury hotels that satisfy all the vacation must-haves to affordable accommodations perfect for those on a budget. You can search our vast catalog of possibilities and pick the accommodation that is ideal for you and your family. With AARP Travel Center's Great Barrington hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Great Barrington
Great Barrington is the perfect town when you have to get away from it all. With only around 6,907 people in the area, this quaint town is just right for a quite vacation. If you need a scenic backdrop, the mountains are close by from Great Barrington. A lot of visitors enjoy the chance to experience the great outdoors.
If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.
Book Together and Save
As an AARP Member, you get to cash in on all the great savings. You can save on select hotels worldwide, flights, and also rental cars. No matter what Great Barrington vacation package you pick, you can rest easy knowing that you already saved on your trip. So what are you waiting for? Book now and get ready for your Great Barrington vacation.
Top 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 ...
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 ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd 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 helpful staff and the ...
Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd 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 helpful staff and the ...
The Little Lion
506 Stockbridge Road Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. ...
East Rock Inn
304 State Rd Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Popular attractions Housatonic River and Housatonic River Walk are located ...
Gedney Farm
34 Hartsville-New Marlborough Rd Great Barrington MA
Stay at this hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are ...
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 ...
Pocketbook Hotel and Bath
549 Washington Street Hudson NY
Stay at this hotel in Hudson. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Oakdale Beach and Hudson Area Library are located ...
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 ...
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. ...
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. ...
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 ...
Don't see what you're looking for?
See all available properties in 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.
Fri, Nov 6 - Mon, Nov 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$181
Roundtrip
found 1 hour ago
Sat, Dec 19 - Thu, Dec 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$224
Roundtrip
found 5 days ago
Thu, Dec 24 - Tue, Jan 5
MCO
Orlando Intl.
BDL
Bradley Intl.
$280
Roundtrip
found 5 days ago
Sun, Dec 20 - Wed, Jan 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$300
Roundtrip
found 5 days ago
Wed, Nov 4 - Tue, Nov 17
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$307
Roundtrip
found 9 hours ago
Best neighborhoods in Great Barrington
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More Types of Hotels
- Hotels with Air Conditioning in Great Barrington
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- Hotels with Complimentary Breakfast in Great Barrington
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- Luxury Hotels in Great Barrington
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- Resorts & Hotels with Spas in Great Barrington
- Pet-friendly Hotels in Great Barrington
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- Hotels with an Indoor Pool in Great Barrington
- Hotels with Balconies in Great Barrington
- Hotel with a Concierge in Great Barrington
- Casinos in Great Barrington
- Hotels with smoking rooms in Great Barrington