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A calm lake reflecting a forest with autumn foliage.

Stockbridge
Massachusetts
United States of America
North America
Hotwire.com

Stockbridge Flight + Hotel Packages

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

The Ponds at Foxhollow

3 out of 5

Save 100% on your flight

Price was $956, price is now $695 per person

$695

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 Cornell Inn, Lenox & The Berkshires

3.5 out of 5

Save 100% on your flight

Price was $1,305, price is now $906 per person

$906

per person

Oct 22 - Oct 26

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.

Prospect Berkshires

3 out of 5

Price was $3,109, price is now $2,191 per person

$2,191

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.

The Perch Hotel

2 out of 5

Price was $2,094, price is now $1,594 per person

$1,594

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Saratoga Casino Hotel

4 out of 5

Price was $1,189, price is now $942 per person

$942

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) 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.

Coffee is terrible! Everything else was solid

Reviewed on Sep 8, 2026

Pocketbook Hotel and Bath

2 out of 5

Price was $1,376, price is now $1,091 per person

$1,091

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

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 nearby.

We stay here all the time. Love everything about this place. Front staff is amazing. The dipping pools are amazing. Rudy, the bartender best guy ever at the bar, have to see him. You will not be disappointed. Great location also

Reviewed on Sep 8, 2026

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5

Price was $933, price is now $741 per person

$741

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Our room was amazingly spacious and clean, and the area is also very peaceful and quiet. We were only there for 2 nights but it was a good experience. Would consider staying there again next time we visit the Berkshires.

Reviewed on Sep 7, 2026

Brook Bound Inn

2 out of 5

Price was $1,397, price is now $1,129 per person

$1,129

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!

Reviewed on Aug 30, 2026