Find Luxury Hotels in Jacksonville, VT

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Check availability on Jacksonville Luxury Hotels

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Jacksonville luxury hotels

Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
The Four Chimneys Inn
Reception
South Shire

South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (118)
"Great period decor! Spacious rooms and an inviting living room to relax. Also walking distance to downtown shops and restaurants was a real plus!"
United States
Roseann
The price is NT$5,518
NT$6,358 total
includes taxes & fees
Jan 4 - 2026/1/5
South Shire
Garden
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (15)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Exterior
Inn on Putney Road

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is NT$7,377
NT$8,114 total
includes taxes & fees
Jan 1 - 2026/1/2
Inn on Putney Road
Lobby
Chesterfield Inn

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is NT$9,667
NT$10,488 total
includes taxes & fees
Jan 13 - 2026/1/14
Chesterfield Inn
Restaurant
The Hermitage Inn Vermont

The Hermitage Inn Vermont

The Hermitage Inn Vermont
4.0 star property
West Dover
9.2 out of 10, Wonderful, (15)
"Great stay,beautiful property!"
United States
Vibhavasu
The Hermitage Inn Vermont
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.
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Top Jacksonville Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Courteous staff "
Susan 1-night trip
Posted 7 days ago
Hotel Downstreet, an Ascend Collection Hotel

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Jacksonville?
Use Expedia to arrange your flight to Rutland, VT (RUT-Rutland Southern Vermont Regional) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Jacksonville has to offer. Jacksonville has some interesting things to see and do including Jacksonville Pond and H.O. Cook State Forest, so you might want to take in the local sights during your visit.
When can I expect good weather in Jacksonville?
Planning for the weather is a good way to make your trip to Jacksonville relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Jacksonville are January, March, November, and February, with each month seeing an average of 9 inches of snowfall.
What's there to see and do in Jacksonville?
Enjoy all that Jacksonville has to offer and visit Jacksonville Pond, Mount Snow, and The Ledge. If you have extra time while you're in the area, you might want to stop by Molly Stark State Park and Harriman Reservoir.

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