Southern Vermont Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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 Southern Vermont vacation rentals

Pool
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very Good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is P23,825
P29,614 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Long Trail House at Stratton Mountain Resort
Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveler
The price is P11,471
P35,377 total
includes taxes & fees
Dec 28 - Dec 29
Wilmington Retreat Near Trails, Skiing & Festivals
Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
Arlington
8.0 out of 10, Very Good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
The price is P15,469
P41,161 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Interior
Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall
3.0 star property
Bondville
The price is P46,767
P76,182 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Vermont Hotel Reviews

Chalet 239

Chalet 239

10/10 Excellent
"It was great! Would stay here again, loved the TV and fiended when we saw there was a hot chocolate machine. Totally recommend, nice people and super close to the slopes so we could wake up late."
Stella 3-night trip
Posted 1 day ago
Chalet 239

Find out more about Southern Vermont

Search for holiday rentals in Southern Vermont on Expedia! You can easily find your home rentals, villas, holiday apartments in Southern Vermont using one of the methods below:

  • View our selection of featured holiday rentals in Southern Vermont
  • Use the map to find apartments and other holiday homes in the Southern Vermont neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southern Vermont while they last

Look no further and take a look at our great range of rental properties in Southern Vermont!