Search Deals on
Bennington Vacation Packages

Build your package with 2 more options

Bennington Flight + Hotel Packages

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

Saratoga Casino Hotel

4 out of 5
Price was $552, price is now $438 per person
$438
per person
Nov 25 - Nov 28
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 Racetrack and Saratoga Performing Arts Center are located nearby.
Very nice hotel. Casino was large and clean. Enjoyed the complimentary soda and coffee. Lots of parking. Very friendly staff. Close to downtown.

Reviewed on Oct 20, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,522, price is now $1,022 per person
$1,022
per person
Dec 17 - Dec 20
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $835, price is now $606 per person
$606
per person
Dec 3 - Dec 6
found 2 days 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.

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

3 out of 5
Save 100% on your flight
Price was $1,846, price is now $1,372 per person
$1,372
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
Book a stay at this business-friendly cottage in Ghent. Enjoy free parking, in-room washers/dryers, and in-room fireplaces. Popular attractions High Falls Trail and Hudson Chatham Winery are located nearby.
The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life. The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure.

Reviewed on Aug 23, 2025

South Shire

South Shire

4 out of 5
Price was $1,507, price is now $1,133 per person
$1,133
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants.

Reviewed on Oct 21, 2026

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Price was $853, price is now $679 per person
$679
per person
Jan 4 - Jan 8
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Birch Body Care and Senate House State Historic Site are located nearby.
Despite saying there was complimentary coffee in the rooms, there was no coffee machines or anything to make coffee in the rooms. The kitchen was several blocks away too.

Reviewed on Oct 21, 2026

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Price was $1,112, price is now $905 per person
$905
per person
Jan 4 - Jan 8
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this cottage in Stone Ridge. Enjoy free parking, patios, and in-room fireplaces. Popular attractions Tongore Park Beach and Century House Historical Society are located nearby.
Wonderful

Reviewed on Mar 29, 2026

The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Save 100% on your flight
Price was $3,643, price is now $2,964 per person
$2,964
per person
Dec 17 - Dec 20
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Book a stay at this historic guesthouse in Catskill. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Kaaterskill Falls and North-South Lake Campground & Day Use Area are located nearby.
Everything was amazing. Shawn was awesome. He greeted you when we came in. It's definitely experiences. All I can say we had a great time. A little quirky.Amazing history set on 200 acres closed down zoo

Reviewed on Sep 21, 2026

Bennington Vacation Packages 3-4 Night Stays

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

Saratoga Casino Hotel

4 out of 5
Price was $552, price is now $438 per person
$438
per person
Nov 25 - Nov 28
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 $1,522, price is now $1,022 per person
$1,022
per person
Dec 17 - Dec 20
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $835, price is now $606 per person
$606
per person
Dec 3 - Dec 6
found 2 days ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
South Shire

South Shire

4 out of 5
Price was $843, price is now $614 per person
$614
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Bennington Vacation Packages 5-7 Night Stays

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

South Shire

4 out of 5
Price was $1,507, price is now $1,133 per person
$1,133
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,778, price is now $1,317 per person
$1,317
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

3 out of 5
Save 100% on your flight
Price was $1,846, price is now $1,372 per person
$1,372
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
Manchester Village Historic District
Price was $1,807, price is now $1,479 per person
$1,479
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

Top Flight Deals

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

Allegiant Air
Thu, Oct 29 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$189 Roundtrip, found 17 hours ago
$189
Roundtrip
found 17 hours ago
Select Allegiant Air flight, departing Thu, Oct 29 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sat, Nov 14, priced at $189 found 17 hours ago
Bargain Flight
Sat, Oct 24 - Sat, Oct 31
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$220 Roundtrip, found 15 hours ago
$220
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Sat, Oct 24 from Charlotte-Douglas Intl. to Albany Intl., returning Sat, Oct 31, priced at $220 found 15 hours ago
United
Sat, Dec 5 - Tue, Dec 8
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$257 Roundtrip, found 2 hours ago
$257
Roundtrip
found 2 hours ago
Select United flight, departing Sat, Dec 5 from Sky Harbor Intl. to Albany Intl., returning Tue, Dec 8, priced at $257 found 2 hours ago
Bargain Flight
Thu, Dec 24 - Tue, Jan 5
TPA
Tampa Intl.
ALB
Albany Intl.
$272 Roundtrip, just found
$272
Roundtrip
just found
Select Bargain Flight flight, departing Thu, Dec 24 from Tampa Intl. to Albany Intl., returning Tue, Jan 5, priced at $272 just found