Weatogue Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

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
27.11 km from city center
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
27.33 km from city center
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
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
19.38 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 ...
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
17.01 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 breakfast and the helpful ...
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
30.67 km from city center
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 ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
18.76 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 ...
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
18.68 km from city center
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 ...
Blackberry River Inn

Blackberry River Inn

3 out of 5
538 Greenwoods Rd W, Norfolk, CT
10.73 km from city center
Stay at this 3-star B&B in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd, Egremont, MA
18.61 km from city center
Stay at this 3-star hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount ...
The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23, Hillsdale, NY
19.91 km from city center
Stay at this motel in Hillsdale. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Catamount Aerial Adventure Park and Community Library ...
the Alander

the Alander

2.5 out of 5
7519 NY-22, Copake, NY
15.7 km from city center
Stay at this lodge in Copake. Enjoy free WiFi, free parking, and rainfall showerheads. Our guests praise the helpful staff in our reviews. Popular attractions ...
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
21.26 km from city center
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. ...
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2 out of 5
980 Pleasant Street, Lee, MA
27.89 km from city center
Book a stay at this business-friendly motel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 out of 5
74 Interlaken Road, Lakeville, CT
12.34 km from city center
Stay at this 3.5-star spa hotel in Lakeville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the property condition in our reviews. Popular ...
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road, Great Barrington, MA
22.46 km from city center
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
Don't see what you're looking for?
See all available properties in Weatogue
View all properties
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.

Frontier Airlines
Fri, Dec 5 - Mon, Dec 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Orlando Intl. to Bradley Intl., returning Mon, Dec 8, priced at $68 found 2 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Bradley Intl., returning Sun, Dec 7, priced at $96 found 2 days ago
JetBlue Airways
Wed, Feb 4 - Sun, Feb 8
TPA
Tampa Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Feb 4 from Tampa Intl. to Bradley Intl., returning Sun, Feb 8, priced at $137 found 1 day ago
Spirit Airlines
Fri, Oct 24 - Fri, Oct 31
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$183 Roundtrip, found 13 hours ago
$183
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Fri, Oct 24 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Oct 31, priced at $183 found 13 hours ago
American Airlines
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Dec 4 from Orlando Intl. to Bradley Intl., returning Sun, Dec 7, priced at $187 found 2 days ago