Deals on vacations and trips to Bennington County

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

Manchester

Vacations
Manchester
A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington

Vacations
Bennington

Bennington County flight + hotel vacation packages

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

Deerfield Valley Inn

2 out of 5
Save 100% on your flight
Price was $624, price is now $435 per person
$435
per person
Sep 17 - Sep 24
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. A free bus station shuttle is offered as well. A 24-hour business center, a garden, and a lobby fireplace are also on offer.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Save 100% on your flight
Price was $1,290, price is now $814 per person
$814
per person
Sep 17 - Sep 24
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
This hotel's 8 hot tubs and 24-hour gym are among the featured amenities. Families will appreciate the arcade/game room and picnic area. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Save 100% on your flight
Price was $1,352, price is now $956 per person
$956
per person
Sep 17 - Sep 24
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $960, price is now $715 per person
$715
per person
Sep 17 - Sep 24
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Save 100% on your flight
Price was $1,046, price is now $783 per person
$783
per person
Sep 17 - Sep 24
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.

Top Bennington County hotels deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Free Cancellation
$271 nightly
The price is $298 total per night
$298 total
Jul 21 - Jul 22
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
Pool
Pet friendly
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
$114 nightly
The price is $124 total per night
$124 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features a gym and an outdoor tennis court. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.
Pool
Breakfast included
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Free Cancellation
$140 nightly
The price is $154 total per night
$154 total
Jul 12 - Jul 13
Total with taxes and fees
This smoke-free hotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the indoor pool and free perks like continental breakfast and free self parking. You'll appreciate the seasonal outdoor pool, bar/lounge, and free newspapers.
Pool
Hot Tub
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $160 total per night
$160 total
Jul 19 - Jul 20
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Free Cancellation
Reserve now, pay when you stay
$219 nightly
The price is $241 total per night
$241 total
Jul 28 - Jul 29
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Pool
Hot Tub
The Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A Manchester Center VT
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $175 total per night
$175 total
Aug 3 - Aug 4
Total with taxes and fees
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.
Pool
Breakfast included
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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.

Stay near popular Bennington County attractions

A calm lake reflecting a forest with autumn foliage.
Photo by Marc Stempel
Open Photo by Marc Stempel

Emerald Lake State Park

You can take time to visit Emerald Lake State Park during your travels to East Dorset. Discover the mountain views in this quaint area.
See properties

Photos of local treasures

Browse Bennington County vacation photos for more inspiration

A house on a grassy hill surrounded by autumn-colored trees.
A statue with outstretched arms and a tall obelisk in the background.
A snow-capped mountain with a forested foreground and a cloudy sky.
A red covered bridge over a river, surrounded by greenery and trees.
A red covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 6 ft.

Frequently asked questions

How much are vacation packages to Bennington County?
With Travelocity vacation packages, you can be living it up in Bennington County for only $435. Flights, tours and hotels — we've got you covered. You can save some cash just by bundling together your bookings. With everything taken care of before leaving, you won't have a care in the world.
Where can I get the best vacation package deals for Bennington County?
It's simple — look no further than Travelocity. With as many as 400 airlines and 1,000,000 worldwide properties, it's a breeze to craft a Bennington County package deal that satisfies your wanderlust.
Why should I purchase my Bennington County vacation package via Travelocity?
Incredible savings, an abundance of breathtaking destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always score the best possible deal with Travelocity.
Can I save on my Bennington County car rental if I bundle it with my hotel or flight?
Combining your bookings into a Bennington County vacation package will leave you with a nice chunk of spare change. You can book a flight and car; a flight, hotel and car; or a hotel and car. You won't find a better way to explore the greater Bennington County area than with your own ride. You can also add experiences and activities to your Travelocity package.
What is the best time of year to go to Bennington County?
Vacationing in the quieter months of the year, March, April and November, comes with a few upsides — think better-value airfares and hotels and less pushing past throngs of tourists. But there's magic in the air during the high season. More events will be planned and more attractions will be open in January, June and August. If you're traveling on a budget, has the thriftiest hotel rates. You'll pay more for a bed in .
Which airport is best for Bennington County?
Flying to Bennington County means you'll step off the plane at Albany Intl. Airport (ALB) or Rutland Southern Vermont Regional Airport (RUT).
What is there to do in Bennington County?
A vibrant and lively destination, Bennington County offers some incredible tourist attractions. Bromley Mountain Ski Resort and Vermont Summer Festival are some of the favorites.

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