Search Vacation Homes in Southern Vermont

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Sep - 21 Sep
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Vacation Homes in Southern Vermont

Our top choices for Southern Vermont vacation homes

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (257)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AED 551
AED 837 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Smart TV, fireplace, table tennis

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

10.0 out of 10, Exceptional, (4)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is AED 426
AED 1,598 total
includes taxes & fees
2 Sep - 3 Sep
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
House, 3 Bedrooms | Exterior

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

3.0 star property
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. "
The price is AED 892
AED 2,315 total
includes taxes & fees
7 Sep - 8 Sep
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Peaceful Stay at Birds of a Feather Farm & Spa
Interior

Peaceful Stay at Birds of a Feather Farm & Spa

9.8 out of 10, Exceptional, (22)
"Great little quiet and peaceful spot that was still very close to Bennington and Manchester.Neighborhood was good for walks or gravel rides."
The price is AED 430
AED 983 total
includes taxes & fees
3 Sep - 4 Sep
Peaceful Stay at Birds of a Feather Farm & Spa
The Mountain Escape!
Outdoor spa tub

The Mountain Escape!

9.8 out of 10, Exceptional, (18)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is AED 424
AED 2,061 total
includes taxes & fees
2 Sep - 3 Sep
The Mountain Escape!
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"The place was deserted "
The price is AED 261
AED 886 total
includes taxes & fees
2 Sep - 3 Sep
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2 bedrooms, WiFi, bed sheets

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
The price is AED 932
AED 1,821 total
includes taxes & fees
2 Sep - 3 Sep
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AED 455
AED 1,084 total
includes taxes & fees
22 Sep - 23 Sep
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is AED 1,273
AED 2,330 total
includes taxes & fees
10 Sep - 11 Sep
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

10.0 out of 10, Exceptional, (12)
"Great property, plenty of space and room for all. Location is ideal"
The price is AED 738
AED 1,876 total
includes taxes & fees
11 Sep - 12 Sep
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Farm Stay in Jasper MO
Interior

Farm Stay in Jasper MO

The price is AED 682
AED 1,331 total
includes taxes & fees
2 Sep - 3 Sep
Farm Stay in Jasper MO
The White Birch near Mount Snow
Smart TV, fireplace

The White Birch near Mount Snow

The price is AED 785
AED 2,069 total
includes taxes & fees
1 Oct - 2 Oct
The White Birch near Mount Snow
Ski in Ski out Condo! Pool access
Terrace/patio

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is AED 567
AED 1,862 total
includes taxes & fees
2 Sep - 3 Sep
Ski in Ski out Condo! Pool access
Cozy 2-bedroom RV with WiFi, AC in welcoming Orange
Private kitchen

Cozy 2-bedroom RV with WiFi, AC in welcoming Orange

The price is AED 727
AED 1,157 total
includes taxes & fees
2 Sep - 3 Sep
Cozy 2-bedroom RV with WiFi, AC in welcoming Orange
Family Friendly Hilltop House In Putney Vermont
Property grounds

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is AED 716
AED 1,255 total
includes taxes & fees
13 Sep - 14 Sep
Family Friendly Hilltop House In Putney Vermont
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Smart TV, fireplace, video games, offices

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

10.0 out of 10, Exceptional, (15)
"We loved the house, the deck and the property amenities."
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Fridge, microwave, oven, stovetop

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

9.0 out of 10, Wonderful, (2)
"Our family had the best time staying here. The home was spacious and gave our two young children plenty of room to roam and explore. It was also close enough to the main road where everything was accessible but also isolated enough where you feel like you're getting away. Erin was great about answering any questions and making sure our stay was comfortable. We'd definitely return here!"
The price is AED 999
AED 2,179 total
includes taxes & fees
14 Sep - 15 Sep
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
The price is AED 1,845
AED 3,874 total
includes taxes & fees
12 Sep - 13 Sep
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking
Interior

Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking

10.0 out of 10, Exceptional, (20)
"Super nice place (very clean and modern) in a quiet area."
Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking
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.
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

Explore a world of travel with Expedia

Explore a world of travel with Expedia