Book Exclusive Jacksonville Vacation Packages

Choose one or more items to build your trip:

Top Jacksonville hotels deals

Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville Cabin w/ Wraparound Deck & Views

Get rates
Book a stay at this family-friendly cabin in Jacksonville. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Honora Winery and Jacksonville Pond are located nearby.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $143 per night
CA $143
per night
Oct. 3 - Oct. 4
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and United States Navy Seabee Bridge are located nearby.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $244 per night
CA $244
per night
Sep. 27 - Sep. 28
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $152 per night
CA $152
per night
Sep. 30 - Oct. 1
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Massachusetts Museum of Contemporary Art and Studio 21 South are located nearby.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $172 per night
CA $172
per night
Sep. 22 - Sep. 23
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way, West Dover, VT
Free cancellation
The price is CA $232 per night
CA $232
per night
Oct. 22 - Oct. 23
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
Don't see what you're looking for?
See all available properties in Jacksonville
View all properties
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

Image for Jacksonville Pond

Jacksonville Pond

Explore the great outdoors at Jacksonville Pond, a lovely green space in Jacksonville. Discover the area's mountain views and seek out the ski slopes.

Jacksonville Pond

Jacksonville Vacations

Get your adventure off to an awesome start by brushing up on Jacksonville before you jet off.

If you travel 13 miles (21 kilometers) southwest of Brattleboro, or 16 miles (26 kilometers) northwest of Greenfield, you'll find yourself in Jacksonville.

Are you eager to mingle with the locals? That shouldn't be too difficult. 200 people call this part of Windham County home.

Places to visit in Jacksonville

Wine labels usually only tell us a fraction of the story about the drop inside. Why not pay a visit to Honora Winery for the full history behind their blends? Need more ideas? Whether they're enclosed by icy mountains or a much-needed oasis in the middle of a dry, desolate landscape, there's something truly special about lakes. Venture out and see what the view's like at Jacksonville Pond. And that's not all there is. Are you looking to reduce the stresses of your hectic life? Savor the fresh air as you go for a romp through Molly Stark State Park.

Where do you fly into for Jacksonville?

Put your seat in the upright position and get set to explore Jacksonville! Once you disembark at Bradley International Airport (BDL), the busy main streets will be just 60 miles (97 kilometers) to the north from here.

Frequently asked questions

How much are vacation packages to Jacksonville?
With vacation packages being sold from as low as , there’s no need to drain your bank balance for your visit to Jacksonville. Travelocity can help. Bundle your experiences, hotels and flights into a convenient package and score some exciting discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Jacksonville?
Book your dream vacation with Travelocity. With access to 400 airlines and at least 1,000,000 hotels around the world, creating the ultimate Jacksonville package deal couldn’t be simpler.
Why should I book my Jacksonville vacation package with Travelocity?
We’ve got a destination for every kind of globetrotter, top-notch service and 24/7 support. And to top all that off, we’ll match any cheaper price you happen to find with our Price Match Guarantee.
Can I save money on my Jacksonville car rental if I combine it with hotels and flights?
Sure can — combine your car, hotel and flight into a Jacksonville vacation package and you can save a ton. With so much to see in Jacksonville, that rental vehicle will come in handy. Once you’re in the driver’s seat, put the stereo on and make your way to Fenway Park, a famous sight approximately 153 kilometers from Jacksonville.
Which airport is best for Jacksonville?
Bradley Intl. Airport (BDL) (97 kilometers away from the downtown area), Albany Intl. Airport (ALB) (80 kilometers away from central Jacksonville) and Rutland Southern Vermont Regional Airport (RUT) (80 kilometers away from central Jacksonville) are the main options in Jacksonville.
Where should I stay when visiting Jacksonville?
The Peaceful Cabin in the Woods and near the mountains is popular with many travelers. Book as soon as possible before it’s too late.

Photos of local treasures

Browse Jacksonville vacation photos for more inspiration