Book Exclusive Jacksonville Vacation Packages

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Jacksonville flight + hotel packages

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

Killington Haus

2 out of 5
Price was CA $956, price is now CA $938 per person
CA $938
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this guesthouse in Killington. Enjoy free WiFi, free parking, and a restaurant. Popular attractions Killington Resort and Black Dog Sports are located nearby.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
Price was CA $1,148, price is now CA $1,082 per person
CA $1,082
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this motel in Londonderry. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Magic Mountain Ski Resort and Lowell Lake State Park are located nearby.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was CA $1,184, price is now CA $1,138 per person
CA $1,138
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was CA $1,208, price is now CA $1,163 per person
CA $1,163
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Silver Bay YMCA Inn and Conference Center

Silver Bay YMCA Inn and Conference Center

2 out of 5
Price was CA $989, price is now CA $971 per person
CA $971
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Book a stay at this beach hotel in Silver Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Lake George and Huletts Landing Marina are located nearby.

Top Jacksonville hotels deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is CA $222 per night
CA $222
per night
Jun 30 - Jul 1
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free cancellation
Reserve now, pay when you stay
The price is CA $171 per night
CA $171
per night
Jun 3 - Jun 4
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Pet-friendly
Parking included
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 $169 per night
CA $169
per night
Jun 14 - Jun 15
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.
Pool
Hot tub
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
231 River Street North Adams MA
Free cancellation
Reserve now, pay when you stay
The price is CA $285 per night
CA $285
per night
Jun 4 - Jun 5
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bracewell Park and Massachusetts Museum of Contemporary Art are located nearby.
Pool
Hot tub
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Free cancellation
The price is CA $201 per night
CA $201
per night
Jul 1 - Jul 2
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Pool
Hot tub
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is CA $188 per night
CA $188
per night
Jun 3 - Jun 4
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
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

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 CA $938, 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