Brattleboro Vacation Packages 2025 from $512

Brattleboro flight + hotel vacation packages

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

The Shire Woodstock

per person

May 19 - May 23

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

Winterplace at Okemo

Clock Tower Base Area

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-out, laundry facilities, and barbecue grills are also on offer.

Jackson Gore Village

Jackson Gore Base Area

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. 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.

Solitude Village at Okemo

Clock Tower Base Area

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. A gym, a hot tub, and a sauna are also on offer.

Okemo Mountain Lodging

Clock Tower Base Area

per person

Jun 21 - Jun 28

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

This vacation home features laundry facilities. Take advantage of the free self parking.

Top Brattleboro hotels deals

Hampton Inn Brattleboro

1378 Putney Road, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$111

includes taxes & fees

$101 per night

Apr 28 - Apr 29

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Colonial Motel And Spa

889 Putney Rd, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$120

includes taxes & fees

$109 per night

Apr 20 - Apr 21

This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$119

includes taxes & fees

$108 per night

Apr 22 - Apr 23

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Latchis Hotel

50 Main Street, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$141

includes taxes & fees

$128 per night

Apr 21 - Apr 22

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.

Pet friendly

Parking included

Holiday Inn Express Hotel & Suites Brattleboro by IHG

100 Chickering Drive, Brattleboro, VT

Free Cancellation

$158

includes taxes & fees

$144 per night

Apr 27 - Apr 28

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Pool

Breakfast included

Vikings Villages Resort

360 Stony Hill Rd South, Guilford, Brattleboro, VT

Free Cancellation

Reserve now, pay when you stay

$184

includes taxes & fees

$169 per night

Apr 21 - Apr 22

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.

Parking included

Free WiFi

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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

The Stone Church

4.5/5(9 reviews)

After visiting The Stone Church, make a plan to see the other sights and activities in Brattleboro. While you're here, you can savor the top-notch restaurants.

Brattleboro Farmers' Market

4/5(31 reviews)

You can enjoy retail therapy at Brattleboro Farmers' Market during your visit to West Brattleboro. Discover the area's entertainment venues, or seek out its ski slopes.

Brattleboro Common

Explore the great outdoors at Brattleboro Common, a lovely green space in Brattleboro. Experience the area's entertainment venues and art scene.

Frequently asked questions

How much are vacation packages to Brattleboro?

Epic adventures await in Brattleboro, with Travelocity vacation packages from as low as $512. Including both hotels and flights, these terrific deals make it really easy to explore every corner of the globe.

How long should my Brattleboro vacation be?

Your Brattleboro break can be as long or as short as you like, but most people stay around 2 nights. Hoping to get out and discover some lesser-known attractions? Lock in an extra night or two and experience another side of this destination.

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

Snapping up the perfect package deal to Brattleboro is a piece of cake with Travelocity. With as many as 400 air carriers and 1,000,000 properties worldwide, you’ll have loads of choice when it comes to picking your flights and hotels.

Why should I purchase my Brattleboro vacation bundle via Travelocity?

Because you’ll never wander on your own if you book your vacation with us, and we offer round-the-clock support and first-rate service to boot. Add to that our Price Match Guarantee and tons of experiences to select from. It’s our job to help you have the trip of a lifetime.

Will I save money on my Brattleboro car rental if I book it with hotels and flights?

With a Brattleboro vacation package, you can combine your flight, car and hotel bookings and save a ton. If you’re eager to uncover the best of this fantastic part of the world, why not make a beeline for Fenway Park? This renowned sight is 80 mi from Brattleboro. With your own wheels, you’ll be there in a flash.

Which airport is best for Brattleboro?

For many wanderers, a trip to Brattleboro means going through Manchester-Boston Regional Airport (MHT). This popular airport is situated 55 mi east of the city center. You could also opt to jet into Lebanon Municipal Airport (LEB) (55 mi away from central Brattleboro) or Rutland Southern Vermont Regional Airport (RUT) (50 mi away from central Brattleboro).

What is there to do in Brattleboro?

There is a certain kind of magic as you roam the streets of Brattleboro. The Stone Church and Brattleboro Bowl are just a couple of highlights that make this city so special, so put them at the top of your list of places to see.

Where should I stay when visiting Brattleboro?

Many people choose to hit the hay at the Colonial Motel And Spa. It’s an excellent base for your Brattleboro getaway.