Bennington County Vacation Packages

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Your Bennington County Vacation

Set off on your next big adventure with a Bennington County vacation package, and leave relaxed knowing all the details are already organized. And with the ability to customize your escape, it'll be one to remember. With so many things to do and see on a trip to Bennington County, it can be tricky to know where to begin. Kick off your travels in Bennington at Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display — two much-loved attractions here. Another city worthy of a spot on your itinerary is Dorset. Don't miss Hildene and Vermont Summer Festival. When you're ready to stop dreaming and start doing, Expedia will help turn your Bennington County vacation into a reality.

Top vacation destinations in Bennington County

FlightsFlightsHotelsHotels

Peru

Peru

Top Bennington County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Oct 10 - Oct 12
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Rutland (RUT)
8.6/10 Excellent! (1,001 reviews)
Carpets are very dirty. Appears worn and in need of an update.

Reviewed on Jul. 14, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
per person
Oct 10 - Oct 12
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Rutland (RUT)
9.2/10 Wonderful! (403 reviews)
Excellent. Jeanine was so kind and helpful. Really cute sitting room. Sauna was awesome. Quiet and clean!

Reviewed on May 25, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
per person
Oct 10 - Oct 12
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Rutland (RUT)
6.4/10 (1,003 reviews)
This property is a suitable place to stay for a place to sleep. The check in staff was friendly and it was quick. The room was equipped with basic amenities like fridge, microwave and soaps - however, the property had a distinct odor in the hallways and clearly the entire property had previously been smoked in. The level of cleanliness was lacking a bit. I would find another property the next time I am in the area.

Reviewed on Jul. 13, 2025

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
per person
Oct 10 - Oct 12
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
9.6/10 Exceptional! (10 reviews)
We truly enjoyed our one night stay! The indoor space was cute. The owners were pleasant. The surrounding grounds were so pretty. The fire pit at night was perfect after a full day of sight seeing. So glad we visited!

Reviewed on Jul. 13, 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
per person
Oct 10 - Oct 12
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Rutland (RUT)
9/10 Wonderful! (44 reviews)
Very nice place only negative was the sauna did not work

Reviewed on Apr. 28, 2025

Bennington County Hotel Deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
The price is CA $240 per night from Jul 21 to Jul 22
CA $240
CA $317 total
Jul 21 - Jul 22
includes taxes & fees
9.2/10 Wonderful! (777 reviews)
"Our favorite place to stay in the area"

Reviewed on Jun. 20, 2025

Kimpton Taconic Hotel by IHG
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Jul 27 to Jul 28
CA $193
CA $287 total
Jul 27 - Jul 28
includes taxes & fees
7.2/10 Good! (492 reviews)
"Just love the very historic sence"

Reviewed on Jul. 6, 2025

The Equinox Golf Resort & Spa
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Aug 4 to Aug 5
CA $155
CA $169 total
Aug 4 - Aug 5
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The property was clean and the staff very pleasant, but the key card often stopped working. Also, the doors didn’t close easily (or securely) so we had to keep making sure we secured it after ourselves."

Reviewed on Jul. 13, 2025

Hotel Vervana, Trademark Collection by Wyndham
See all 619 properties in Bennington County
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Bennington County vacation package cost?
From as low as CA $1,158, you can customize your Bennington County vacation package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Bennington County?
Bundle your hotels and flights with Expedia to save on your next exciting adventure. With more than 550 air carriers and 1,000,000 hotel options across the world, your Bennington County vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not include one or two exciting activities and tours? It's an easy way to unlock even more discounts. Your dream vacation in Bennington County is closer than you thought!
What are the top hotels in Bennington County?
When it comes to properties in Bondville, Hampton Inn Bennington and Hampton Inn and Suites Manchester are two great options. If you're heading to Peru, The Equinox Golf Resort & Spa and The Autumn Inn will make you feel right at home.
How far in advance should I book my Bennington County vacation?
To score discount prices, book nice and early. Airlines generally begin selling tickets, along with some of the lowest fares, around 12 months prior to departure. Hotels, car rental and experiences should also be booked early to avoid disappointment. If you've decided on a last-minute getaway in Bennington County, there are always lots of great bargains to be had on Expedia. Check them out now!
What does an Expedia Bennington County travel package include?
Choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can add the fun stuff like activities and tours. Want to pick your airfare class? That's easy to do too. The choice is yours when it comes to arranging your dream Bennington County escape.
What should I know before booking a Bennington County travel package?
Whether it's adventure or relaxation you're chasing, a Bennington County vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Bennington County Expedia vacation package?
Most definitely. We offer more than 550 partner airlines worldwide, so you can customize your Bennington County vacation according to your style and budget.
If I'm not able to travel, can I cancel my Bennington County vacation package?
Don't worry if you're rethinking your Bennington County vacation package --- it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.