Brattleboro Vacation Packages 2026 from $1,043

Brattleboro flight + hotel vacation packages

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

The Vesper

$1,043

per person

Dec 16 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Springfield (VSF)

This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.

Okemo Mountain Lodging by Vail Resorts

Clock Tower Base Area

Save 100% on your flight

$9,351

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Springfield (VSF)

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

The Shire Woodstock

$1,512

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop 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.

Sinclair Inn Bed and Breakfast

$1,066

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Springfield (VSF)

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.

Woodstock Inn & Resort

$3,477

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Springfield (VSF)

This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.

Top Brattleboro hotels deals

Colonial Motel

889 Putney Rd Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$109 total

Nov 1 - Nov 2

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a grocery/convenience store, and a lobby fireplace are also on offer.

Breakfast included

Pet friendly

Latchis Hotel

50 Main Street Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$161 total

Nov 9 - Nov 10

Total with taxes and fees

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

Travelodge by Wyndham Brattleboro VT

1254 Putney Rd Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$68 total

Oct 26 - Oct 27

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pet friendly

Parking included

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

Free Cancellation

$110 nightly

$121 total

Nov 22 - Nov 23

Total with taxes and fees

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

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$121 total

Nov 15 - Nov 16

Total with taxes and fees

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

The Covered Bridge Inn

1043 Putney Road Brattleboro VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$143 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Breakfast included

Parking 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 Brattleboro attractions

The Stone Church

8.6/10 (39 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.

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Frequently asked questions

How much are vacation packages to Brattleboro?

Epic adventures await in Brattleboro, with Travelocity vacation packages from as low as $1,043. 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.