Cheap Vacations in Bennington County

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Bennington County vacations

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

Berkshire Mountain Lodge

3 out of 5
Price was $515, price is now $420 per person
$420
per person
Oct 1 - Oct 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,531, price is now $1,945 per person
$1,945
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
The Whitlock

The Whitlock

2 out of 5
Price was $1,024, price is now $805 per person
$805
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
The White House Inn

The White House Inn

3.5 out of 5
Price was $827, price is now $683 per person
$683
per person
Oct 2 - Oct 4
just found
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $509, price is now $427 per person
$427
per person
Oct 1 - Oct 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $728, price is now $623 per person
$623
per person
Oct 2 - Oct 4
just found
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $672, price is now $580 per person
$580
per person
Oct 2 - Oct 4
just found
Roundtrip non-stop flight included
Indianapolis (IND) to Rutland (RUT)
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $1,122, price is now $970 per person
$970
per person
Oct 16 - Oct 18
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,433, price is now $1,241 per person
$1,241
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Price was $703, price is now $614 per person
$614
per person
Oct 2 - Oct 4
just found
Roundtrip non-stop flight included
Indianapolis (IND) to Rutland (RUT)

3-night Bennington County vacations

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

Berkshire Mountain Lodge

3 out of 5
Price was $515, price is now $420 per person
$420
per person
Oct 1 - Oct 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $509, price is now $427 per person
$427
per person
Oct 1 - Oct 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $788, price is now $670 per person
$670
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $639, price is now $563 per person
$563
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,013, price is now $894 per person
$894
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
The Landgrove

The Landgrove

3.5 out of 5
Price was $759, price is now $671 per person
$671
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $715, price is now $637 per person
$637
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
The White House Inn

The White House Inn

3.5 out of 5
Price was $884, price is now $809 per person
$809
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
Price was $770, price is now $705 per person
$705
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $604, price is now $562 per person
$562
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was $596, price is now $556 per person
$556
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
Price was $676, price is now $630 per person
$630
per person
Oct 1 - Oct 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)

4-night Bennington County vacations

Price found within the past 48 hours. Click for updated prices.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
Price was $659, price is now $620 per person
$620
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
The Whitlock

The Whitlock

2 out of 5
Price was $1,024, price is now $805 per person
$805
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $861, price is now $766 per person
$766
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,055, price is now $940 per person
$940
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,268, price is now $1,133 per person
$1,133
per person
Oct 5 - Oct 9
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $916, price is now $821 per person
$821
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,545, price is now $1,392 per person
$1,392
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $791, price is now $719 per person
$719
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $844, price is now $781 per person
$781
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $803, price is now $751 per person
$751
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was $832, price is now $781 per person
$781
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $865, price is now $813 per person
$813
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)

5-night Bennington County vacations

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

Albany Airport Inn

2.5 out of 5
Price was $614, price is now $501 per person
$501
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,531, price is now $1,945 per person
$1,945
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Price was $833, price is now $688 per person
$688
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Price was $855, price is now $707 per person
$707
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Park Manor Hotel

Park Manor Hotel

4 out of 5
Price was $707, price is now $590 per person
$590
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
Price was $659, price is now $551 per person
$551
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $1,433, price is now $1,241 per person
$1,241
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $1,212, price is now $1,051 per person
$1,051
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Tru By Hilton Albany Airport, NY

Tru By Hilton Albany Airport, NY

2.5 out of 5
Price was $666, price is now $579 per person
$579
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,290, price is now $1,127 per person
$1,127
per person
Oct 19 - Oct 24
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,231, price is now $1,076 per person
$1,076
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
Capital Inn & Suites

Capital Inn & Suites

2 out of 5
Price was $622, price is now $544 per person
$544
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

Top places to visit in Bennington County

A white building with black shutters, a sign for Covey & NY, and an American flag.
FlightsFlightsHotelsHotels

Manchester

Manchester

Flight deals to Bennington County

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

Sun, Sep 6 - Sun, Sep 13
FLL
Fort Lauderdale
ALB
Albany
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Sun, Sep 6 from Fort Lauderdale to Albany, returning Sun, Sep 13, priced at $172 found 2 days ago
Tue, Oct 27 - Thu, Oct 29
ATL
Atlanta
ALB
Albany
$272 Roundtrip, found 5 hours ago
$272
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Tue, Oct 27 from Atlanta to Albany, returning Thu, Oct 29, priced at $272 found 5 hours ago
Wed, Sep 9 - Sat, Sep 12
PHX
Phoenix
ALB
Albany
$303 Roundtrip, found 4 days ago
$303
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Wed, Sep 9 from Phoenix to Albany, returning Sat, Sep 12, priced at $303 found 4 days ago

Top rated hotels for your Bennington County vacation

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street Bennington VT
Free Cancellation
Reserve now, pay when you stay
0.39 mi from city center
$110 nightly
The price is $120 total per night
$120 total
Sep 13 - Sep 14
Total with taxes and fees
With a stay at Hotel Vervana, Trademark Collection by Wyndham, you'll be centrally located in Bennington, a short 8-minute walk from Bennington Museum and 14 minutes by foot from Old First Congregational Church.
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
3567 Main Street Manchester VT
Free Cancellation
Reserve now, pay when you stay
20.59 mi from city center
$227 nightly
The price is $250 total per night
$250 total
Sep 7 - Sep 8
Total with taxes and fees
With a stay at The Equinox Golf Resort And Spa in Manchester (Manchester Village Historic District), you'll be steps from Green Mountain National Forest and Golf Club at Equinox.
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
21.53 mi from city center
$155 nightly
The price is $170 total per night
$170 total
Sep 8 - Sep 9
Total with taxes and fees
With a stay at Hampton Inn and Suites Manchester, you'll be centrally located in Manchester Center, a 1-minute drive from Green Mountain National Forest and 15 minutes from Bromley Mountain Ski Resort.
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See all available properties in Bennington County
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.