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Top Jacksonville hotels deals

The Engel House

The Engel House

3 out of 5
204 VT-112 Jacksonville VT
Get rates
Stay at this B&B in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jacksonville Pond and Honora Winery are located nearby.
Breakfast included
Parking included
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 $148 per night
CA $148
CA $165 total
Dec 20 - Dec 21
includes taxes & fees
Book a stay at this business-friendly 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 MCLA Gallery 51 and North Adams Center are located nearby.
Pool
Hot tub
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
The price is CA $213 per night
CA $213
CA $255 total
Dec 9 - Dec 10
includes taxes & fees
Book a stay at this 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.
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 $198 per night
CA $198
CA $253 total
Jan 8 - Jan 9, 2026
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
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $253 per night
CA $253
CA $283 total
Dec 14 - Dec 15
includes taxes & fees
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Old Greenfield Village and Museum of Our Industrial Heritage are located nearby.
Breakfast included
Pet-friendly
Knotty Pine

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
Free cancellation
Reserve now, pay when you stay
The price is CA $152 per night
CA $152
CA $166 total
Dec 9 - Dec 10
includes taxes & fees
Stay at this motel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bennington Battle Monument and Bennington Museum are located nearby.
Pool
Breakfast 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.

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 , 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