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Bennington Vacation Packages

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Bennington Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Save 100% on your flight
Price was $936, price is now $648 per person
$648
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.
Quiet property. Convenient location.

Reviewed on Aug 2, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,023, price is now $702 per person
$702
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 The Bookstore are located nearby.

Lake Haven Motel

Lake Haven Motel

2.5 out of 5
Save 100% on your flight
Price was $879, price is now $660 per person
$660
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this motel 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.
The location is fantastic! Easy walking distance to all the restaurants and activities in town.

Reviewed on Aug 20, 2026

Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $943, price is now $735 per person
$735
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Yeah, Expedia didn't really feature the fact that this is a true gambling hall attached to a hotel and far away from the main drag in Saratoga Springs. They are doing a good job fulfilling their mission. The room was clean and comfortable. A nice shower. the free slow charger for our EV was great, too.

Reviewed on Aug 19, 2026

Prospect Berkshires

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

The Whitlock

The Whitlock

2 out of 5
Price was $1,025, price is now $811 per person
$811
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.
Lovely room, nice amenities.

Reviewed on Aug 17, 2026

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

3 out of 5
Price was $4,244, price is now $3,467 per person
$3,467
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) 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.

Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

Farmhouse at Leeds by Avantstay Catskills Farmhouse + Barn Suite + Firepit Mins to Hudson + Kaaterskill Falls

3 out of 5
Price was $2,336, price is now $1,913 per person
$1,913
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this cottage in Leeds. Enjoy free parking, patios, and in-room fireplaces. Popular attractions Catskill Golf Club and Thomas Cole National Historic Site are located nearby.

Bennington Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was $633, price is now $522 per person
$522
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
Save 100% on your flight
Price was $1,023, price is now $702 per person
$702
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Save 100% on your flight
Price was $936, price is now $648 per person
$648
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Whitlock

The Whitlock

2 out of 5
Price was $1,025, price is now $811 per person
$811
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)

Bennington Vacation Packages 5-7 Night Stays

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

Lake Haven Motel

2.5 out of 5
Save 100% on your flight
Price was $879, price is now $660 per person
$660
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $1,615, price is now $1,208 per person
$1,208
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $1,287, price is now $993 per person
$993
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $943, price is now $735 per person
$735
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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, Sep 17 - Sun, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$128 Roundtrip, found 3 hours ago
$128
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Thu, Sep 17 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 27, priced at $128 found 3 hours ago
United
Sat, Sep 5 - Sat, Sep 26
LAX
Los Angeles Intl.
ALB
Albany Intl.
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Select United flight, departing Sat, Sep 5 from Los Angeles Intl. to Albany Intl., returning Sat, Sep 26, priced at $261 found 6 days ago
Breeze Airways
Fri, Sep 25 - Sat, Oct 3
TPA
Tampa Intl.
ALB
Albany Intl.
$280 Roundtrip, found 3 hours ago
$280
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Sep 25 from Tampa Intl. to Albany Intl., returning Sat, Oct 3, priced at $280 found 3 hours ago
Bargain Flight
Mon, Sep 21 - Sun, Sep 27
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$291 Roundtrip, found 3 hours ago
$291
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sun, Sep 27, priced at $291 found 3 hours ago