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The Berkshires Vacation Packages

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The Berkshires Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $613, price is now $485 per person
$485
per person
Nov 20 - Nov 23
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this family-friendly guesthouse in Lenox. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,757, price is now $1,168 per person
$1,168
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
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 attractions Tanglewood Music Center and Lenox Library are located nearby.
Great and helpful staff. Delicious complimentary drinks and a free bottle of wine in your room!!

Reviewed on Sep 11, 2026

The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $956, price is now $647 per person
$647
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.
Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely.

Reviewed on Sep 4, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $895, price is now $608 per person
$608
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $3,089, price is now $2,171 per person
$2,171
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
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 are located nearby.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $806, price is now $572 per person
$572
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
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. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat.

Reviewed on Sep 9, 2026

Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Save 100% on your flight
Price was $886, price is now $668 per person
$668
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Kingston. Enjoy free WiFi, room service, and free bicycles on site. Popular attractions Kingston Point Beach and Trolley Museum of New York are located nearby.
Stayed for one night and it was a great place for an anniversary getaway. The views and grounds were beautiful. Our cottage was cozy and perfect. We were able to charge our EV vehicle overnight which was very helpful. The sauna experience was nice and the Pavillion restaurant was excellent.

Reviewed on Aug 28, 2026

Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $1,126, price is now $865 per person
$865
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Racetrack and Saratoga Performing Arts Center are located nearby.
This was our third time here and we love the location and the hotel is beautiful. The casino is very clean and so is the entire place.

Reviewed on Sep 11, 2026

The Berkshires Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $608, price is now $466 per person
$466
per person
Oct 22 - Oct 26
just found
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $956, price is now $647 per person
$647
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,328, price is now $904 per person
$904
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,498, price is now $1,099 per person
$1,099
per person
Oct 15 - Oct 18
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)

The Berkshires Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $806, price is now $572 per person
$572
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,440, price is now $931 per person
$931
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,757, price is now $1,168 per person
$1,168
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $3,089, price is now $2,171 per person
$2,171
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Top Flight Deals

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

Frontier Airlines
Fri, Dec 4 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$82 Roundtrip, found 19 hours ago
$82
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $82 found 19 hours ago
Allegiant Air
Thu, Sep 17 - Sun, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$144 Roundtrip, found 6 days ago
$144
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Sep 17 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 27, priced at $144 found 6 days ago
Frontier Airlines
Wed, Oct 14 - Fri, Oct 23
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Luis Munoz Marin Intl. to Bradley Intl., returning Fri, Oct 23, priced at $161 found 4 days ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$181 Roundtrip, found 1 hour ago
$181
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $181 found 1 hour ago