Wilmington Vacation Packages 2026 from $521

Wilmington flight + hotel vacation packages

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

Berkshire Mountain Lodge

$521

per person

Sep 10 - Sep 13

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$782

per person

Sep 10 - Sep 13

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Prospect Berkshires

$974

per person

Sep 10 - Sep 13

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

Hideaway Inn Lenox

$646

per person

Sep 10 - Sep 13

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.

Hotel On North

$820

per person

Sep 10 - Sep 13

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Top Wilmington hotels deals

The White House Inn

178 Route 9 East Wilmington VT

$219 nightly

$241 total

Jun 28 - Jun 29

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

Breakfast included

Parking included

Valley Craft Ales

18 N Main St Wilmington VT

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$145 total

Jun 26 - Jun 27

Total with taxes and fees

This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a communal living room are also provided.

Parking included

Free WiFi

The Nutmeg

153 West Main St Wilmington VT

$189 nightly

$208 total

Jun 29 - Jun 30

Total with taxes and fees

A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like cooked-to-order breakfast and WiFi in public areas. A garden, a lobby fireplace, and a picnic area are also on offer.

Pool

Breakfast included

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Wilmington VT

Get rates

This chalet features an outdoor pool and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and conveniences like a garden and barbecue grills.

Pool

Hot Tub

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington VT

Get rates

This vacation home features a hot tub and a sauna. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden and laundry facilities are also provided.

Hot Tub

Kitchen

Gold Medal Family Retreat- Deck-Pvt. Hot Tub -Clubhouse Pool, Game Room

Wilmington VT

Get rates

This cabin features an outdoor pool and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the gym and conveniences like a garden and laundry facilities.

Pool

Hot Tub

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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.

Popular places to visit

South Main Street

You can enjoy retail therapy at South Main Street during your visit to Wilmington. While you're here, you can savor the top-notch restaurants.

Molly Stark State Park

You can take time to visit Molly Stark State Park during your travels to Wilmington. Discover the area's mountain views and seek out the ski slopes.

The Hermitage Golf Club

Enjoy a round of golf in Wilmington at The Hermitage Golf Club. Discover the area's mountain views and seek out the ski slopes.

Frequently asked questions

How much are vacation packages to Wilmington?

Get ready to be pleasantly surprised — you can unwind in Wilmington for just $521. At Travelocity, we save you money and stress with our awesome vacation package deals. With experiences, hotels and flights all in one place, why wait?

How long should my Wilmington vacation be?

Most sightseers stay in Wilmington for about 3 nights. That being said, traveling is all about checking out new things and making memories — why not stay a couple of more nights to do just that?

Where can I get the best vacation package deals for Wilmington?

For an amazing Wilmington package deal, head straight to Travelocity. Select from 400 air carriers and 1,000,000 properties worldwide to create your dream adventure — you're spoiled for choice!

Why should I book my Wilmington vacation bundle via Travelocity?

You'll not only save lots, but you'll also have access to our 24/7 customer support, top-notch service and a Price Match Guarantee. Roam across the globe, discover hidden treasures and make unforgettable memories — we'll take care of the little details.

Can I save on my Wilmington car rental if I bundle it with my hotel or flight?

Bundling your hotel, car and flight into a Wilmington vacation package is a great way to land the best deal. Plus, having your own car rental gives you absolute freedom to make your way to all those amazing sights you're itching to see. Sitting 95 mi away from Wilmington, Fenway Park is one attraction that should be on your to-do list. Load up the car and make a day trip of it.

Which airport is best for Wilmington?

Albany Intl. Airport (ALB) is 50 mi from the downtown area and is the starting point for many memorable experiences. Alternatively, Lebanon Municipal Airport (LEB) is 60 mi away from central Wilmington and Rutland Southern Vermont Regional Airport (RUT) is 45 mi away from central Wilmington.

What is there to do in Wilmington?

There's a certain magic as you stroll through the streets of Wilmington. Lake Raponda and The Ledge are just a couple of renowned sights that make this city so special, so put them on your must-see list.

Where should I stay when visiting Wilmington?

If you're after somewhere to spend your nights, check out the The Nutmeg. It's the top pick for many travelers.