Search Deals onThe Berkshires Vacation Packages
The Berkshires Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Vervana, Trademark Collection by Wyndham
Price was $646, price is now $574 per person
$574
per person
Dec 10 - Dec 14
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bennington Museum and Fiddlehead at Four Corners are located nearby.
We had an issue with our room (loud guests above us) and the manager quickly stepped in and moved our room! Amazing!
Reviewed on Nov 6, 2026

Lodges At Cresthaven
Price was $1,055, price is now $745 per person
$745
per person
Jan 7 - Jan 14
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Book a stay at this beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hearthstone Point Campground and Lakeside Trail are located nearby.
My husband and I really enjoyed the stay at this hotel. We were stunned on how beautiful the property was, especially inside the hotel room. Everything was immaculate. We will absolutely be staying here again ❤️ we cannot wait to plan our next adventure here to the Lodges at Cresthaven ❤️
Reviewed on Nov 1, 2026

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18
Save 100% on your flight
Price was $2,837, price is now $2,140 per person
$2,140
per person
Jan 8 - Jan 11
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Stay at this cottage in Earlton. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Thunderhart Golf Course and Cairo Lockwood State Forest are located nearby.

Aspen At Manchester
Price was $1,196, price is now $1,015 per person
$1,015
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.
There was no staff on-site, and all communication was handled through text messages. Other than that, it’s a nice and clean place. Just keep in mind that, there is no daily housekeeping, so be prepared to reuse your towels and bed sheets during your stay.
Reviewed on Nov 4, 2026

Brook Bound Inn
Price was $755, price is now $650 per person
$650
per person
Dec 12 - Dec 15
found 1 hour ago
Roundtrip flight included
New York (LGA) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
The place was clean and beautiful. You need to check with Expedia . I didn’t get the steps to get in, since there is nobody on site. to check in. I call the phone on site. Somebody call me back and walk me through step to get in.
Reviewed on Oct 19, 2026

Wilburton Inn
Price was $1,864, price is now $1,617 per person
$1,617
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this golf hotel in Manchester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Museum of Creative Process and Hildene are located nearby.
Beautiful serene large property with many interesting art sculptures throughout. Close to downtown Manchester but need car.
Very memorable.
Reviewed on Oct 24, 2026

Charming 6 Bdrm Countryside Stay
Price was $2,570, price is now $2,251 per person
$2,251
per person
Dec 25 - Dec 27
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
Stay at this country house in Great Barrington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions W.E.B. Du Bois Boyhood Homesite and Catamount Aerial Adventure Park are located nearby.

The Palmer House Resort, an Ascend Collection Hotel
Price was $924, price is now $819 per person
$819
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lye Brook Falls and Dana L. Thompson Memorial Park are located nearby.
Very clean. Recently updated.
Reviewed on Nov 7, 2026
The Berkshires Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



The Berkshires Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 4 - Mon, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago

Thu, Dec 3 - Mon, Dec 7
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$178 Roundtrip, found 4 hours ago
$178
Roundtrip
found 4 hours ago

Sat, Dec 5 - Tue, Dec 8
TPA
Tampa Intl.
BDL
Bradley Intl.
$189 Roundtrip, found 3 hours ago
$189
Roundtrip
found 3 hours ago

Wed, Jan 13 - Sat, Jan 23
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Popular Vacation Attractions
- Popular Destinations
- Nearby Destinations
- Areas of The Berkshires
- Hotwire Picks
- Jiminy Peak Mountain Resort Vacations
- Tanglewood Music Center Vacations
- Ski Butternut Vacations
- Williams College Vacations
- National Shrine of the Divine Mercy Vacations
- Norman Rockwell Museum Vacations
- Massachusetts Museum of Contemporary Art Vacations
- Lee Premium Outlets Vacations
- Mount Greylock Vacations
- Taconic State Park Vacations
- Catamount Ski Area Vacations
- Bousquet Ski Area Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations



