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Bennington Vacation Packages

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A red covered bridge over a river with greenery and yellow flowers around.

Bennington
Vermont
United States of America
North America
Hotwire.com

Bennington Flight + Hotel Packages

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

Saratoga Casino Hotel

4 out of 5

Price was $522, price is now $386 per person

$386

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

New York (NYC) 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 Casino and Saratoga Racetrack are located nearby.

Very nice hotel Shuttle service to downtown was great.

Reviewed on Aug 26, 2026

Lodges At Cresthaven

4 out of 5

Price was $621, price is now $449 per person

$449

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

New York (NYC) 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 Lake George Steamboat Company and Fort William Henry Museum are located nearby.

Sundowner on Lake George

2.5 out of 5

Price was $745, price is now $573 per person

$573

per person

Oct 6 - Oct 9

found 14 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Book a stay at this beach motel in Lake George. Enjoy free parking, an outdoor pool, and a private beach. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.

Staff extremely nice, the best view. Cozy area very convenient location.

Reviewed on Aug 16, 2026

The Wiltwyck

3.5 out of 5

Price was $1,290, price is now $996 per person

$996

per person

Sep 30 - Oct 6

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.

Charming and spacious apartment in a large historic home. Comfortable bed in cozy bedroom. Location is excellent — just a few minutes’ walk to cafes, bookstores, restaurants, shops and historic sites.

Reviewed on Aug 24, 2026

The Lake George Inn

2 out of 5

Price was $747, price is now $589 per person

$589

per person

Oct 6 - Oct 9

found 14 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this hotel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.

Room was nice but the outside needs updating

Reviewed on Aug 10, 2026

Prospect Berkshires

3 out of 5

Price was $2,140, price is now $1,692 per person

$1,692

per person

Sep 30 - Oct 6

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.

It was beautiful but quite expensive. There was no housekeeping included so trash was not picked up and the breakfasts were grossly overpriced!

Reviewed on Aug 19, 2026

Ambler Hotel

2 out of 5

Price was $922, price is now $746 per person

$746

per person

Oct 6 - Oct 9

found 14 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and Netflix. Popular attractions Saratoga Racetrack and Saratoga Casino are located nearby.

27 Lincoln

2 out of 5

Price was $702, price is now $574 per person

$574

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

Stay at this motel in Saratoga Springs. Enjoy free parking and housekeeping. Popular attractions Saratoga Casino and Saratoga Racetrack are located nearby.