The Bennington County Court House with a white facade, green shutters, and a gold dome.

Southern Vermont Luxury Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Discover the most popular places to visit in Southern Vermont

Skiers on a snowy slope with a ski lift in the background.
Photo by Doug Blackmore/Mount Snow
Open Photo by Doug Blackmore/Mount Snow

Mount Snow

9.2/10 (568 reviews)
This southern Vermont retreat offers 86 trails across four mountain faces for winter thrills. In summer, the resort transforms with downhill mountain biking, hiking trails, and an 18-hole championship golf course.
See properties

Top Luxury Southern Vermont Hotels

A white two-story house with a front porch, a covered patio, and a well-maintained garden.

The Weston

The Weston
5.0 star property
31.5 km from Southern Vermont
9.6 out of 10, Exceptional, (15 reviews)
"The Weston is a spectacular small hotel. The restaurant is delicious and the staff go oabove and beyond to make your stay lovely."
The price is ₩526,752
₩574,159 total
includes taxes & fees
Nov 18 - Nov 19
The Weston
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.
See all properties in Southern Vermont

All you need to know about luxury vacations in Southern Vermont

What can I expect from a luxury Southern Vermont vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Southern Vermont vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Southern Vermont?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Southern Vermont luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at . Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Southern Vermont?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Southern Vermont with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Southern Vermont?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Southern Vermont with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Southern Vermont with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.