Book Exclusive Jacksonville Vacation Packages

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Jacksonville flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was CA $833, price is now CA $782 per person
CA $782
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was CA $915, price is now CA $840 per person
CA $840
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Fire Tower are located nearby.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was CA $857, price is now CA $796 per person
CA $796
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
Price was CA $4,855, price is now CA $4,550 per person
CA $4,550
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rutland (RUT)
Book a stay at this golf castle in Bolton Landing. Enjoy free WiFi, free parking, and furnished balconies or patios. Popular attractions Veterans Memorial Park Beach and Adirondack Extreme Adventure Course are located nearby.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was CA $923, price is now CA $881 per person
CA $881
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Rutland (RUT)
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen 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
Free cancellation
The price is CA $224 per night
CA $224
CA $250 total
Jun 30 - Jul 1
includes taxes & fees
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
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 $211 per night
CA $211
CA $252 total
Jul 9 - Jul 10
includes taxes & fees
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
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 $194 per night
CA $194
CA $214 total
Jun 16 - Jun 17
includes taxes & fees
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 $154 per night
CA $154
CA $169 total
Jul 2 - Jul 3
includes taxes & fees
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
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is CA $209 per night
CA $209
CA $244 total
Jul 5 - Jul 6
includes taxes & fees
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
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
231 River Street North Adams MA
The price is CA $323 per night
CA $323
CA $392 total
Jul 9 - Jul 10
includes taxes & fees
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
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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 $782, 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