Top Bennington Hotel Deals

Make the Most of Your Bennington Stay

Revolutionary history meets modern creativity

Bennington anchors Vermont's southwestern corner with quiet confidence earned through centuries of American history. The 306-foot Battle Monument—the state's tallest structure—commemorates the 1777 Revolutionary War victory. Old Bennington preserves Federal and Colonial architecture along tree-lined streets, where the Old First Church cemetery holds Robert Frost's grave. Bennington College provides striking contrast with International Style buildings by Pietro Belluschi and Edward Larrabee Barnes.

Arts and culinary refinement

The college community creates an atmosphere balancing rural Vermont charm with intellectual curiosity. The Bennington Museum houses the world's largest public collection of Grandma Moses paintings alongside regional artifacts. Dining ranges from French-Vermont cuisine at Four Chimneys Inn to Pangaea's sophisticated fare in colonial North Bennington. Downtown's revitalized scene includes craft breweries and the Basement Music Series.

Gateway to cultural exploration

Bennington provides access to the Massachusetts Berkshires' renowned museums, including MASS MoCA and The Clark, just 20 minutes south. Manchester's outlets and Hildene estate lie 30 minutes north, while Saratoga Springs offers historic resort experiences an hour west. A rental car proves essential for exploring covered bridges and mountain landscapes. Members can apply miles toward accommodations from Victorian estates to properties along Route 7.

Frequently Asked Questions about Bennington

Can I use my miles on Delta Stays to book hotels in Bennington?

Yes, you can book your hotel stay in Bennington using your Delta miles, either for the total amount or in combination with money to reserve your stay. When you log in to your Delta SkyMiles® account, you will also discover Member offers at select properties that could enhance your travel experience.

What is the benefit of booking my Bennington hotel directly on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 spent on completed hotel stays and vacation rentals reserved through Delta Stays. Plus, you will receive access to Member promotions at select properties, along with the option to complete payment using miles, cash, or a combination. To ensure you earn your miles, simply sign in to your SkyMiles account or enter your SkyMiles number at checkout when paying with cash. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Is it possible to change or cancel my hotel booking made through Delta Stays?

Cancellation policies vary by property. We suggest reviewing the cancellation policies displayed in the detailed information for each hotel before completing your reservation. You'll find that some rates are refundable, while others are non-refundable. Any modifications or cancellations to your reservation may affect the mileage credits you earn and receive in your account.

Can I use my Delta SkyMiles® American Express® Card to book?

Yes, your Delta SkyMiles® Gold, Platinum, or Reserve American Express® Card gives you access to additional miles and benefits including an annual statement credit of up to $200 to use on prepaid hotels or vacation rentals booked through Delta Cars and Stays. These offers are subject to specific terms. To explore all the benefits available with your card, please visit the Delta SkyMiles® American Express Credit Cards page for complete details.

Can I earn MQDs on Delta Stays hotel bookings?

Periodically, Delta Stays provides special promotions for SkyMiles Members to earn Medallion® Qualification Dollars on accommodations reserved through their booking service. For the most current MQD earning opportunities and their associated requirements, we recommend visiting the dedicated Delta Stays MQD Offer page where you can review all available offers and their corresponding terms and conditions.

Do I need to have a Delta SkyMiles account to book hotels on Delta Stays?

No, anyone can book hotels through Delta Stays. However, only SkyMiles Members can earn miles and access Member-only prices and offers. As a SkyMiles Member, you will receive 2 miles per $1 spent through Delta Cars and Stays (not including taxes and other charges). Joining the SkyMiles program is entirely free. Become a Member today by visiting the delta.com.

On Delta Stays, can I book a vacation rental?

Yes, Delta Stays offers a wide selection of vacation rentals in addition to hotels. You have access to numerous homes, condos, and specialty lodging options powered by Vrbo to suit your travel preferences. You can discover these alternative accommodations by visiting the Vacation Rentals page.

What hotels in Bennington have high ratings?

You will find 11 hotels in Bennington to choose from when you book on Delta Stays. South Shire has a guest rating of 9 out of 10, and features a restaurant and a bar/lounge.

What's a good time of year to visit Bennington?

To experience Bennington during great weather, consider a visit in July when the temperature is warmest and you can enjoy outdoor activities under sunny skies. For off-peak prices and more deals on hotels, consider visiting during April or May when you'll find fewer crowds and better accommodation rates during this quieter spring season.

Which hotels in Bennington are located closest to Prospect Mountain Cross-Country Ski Center?

Vermont's highest Nordic ski center features 30km of groomed trails for classic and skate skiing across all skill levels. The cozy lodge with its stone fireplace awaits after your mountain routes. South Shire is a popular hotel, which is just a short drive away.

Which hotels in Bennington are located closest to Prospect Mountain Nordic Ski Center?

Glide through 15 miles of cross-country trails winding through snow-covered forests at Prospect Mountain, where the elevated location ensures reliable conditions from December through March. Popular hotels include South Shire which is a short drive away.

Which hotels in Bennington are located closest to Bennington Battle Monument?

This 306-foot obelisk marks a pivotal Revolutionary War victory and stands as Vermont's tallest structure. Take the elevator to the observatory for sweeping views across 3 states. Popular hotels include South Shire which is a short drive away.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar