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

Southern Vermont Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Southern Vermont holiday rentals

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

1. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (84 reviews)
"Nice place and great location!!!"
United States
William
The price is HK$2,785
HK$3,462 total
includes taxes & fees
15 Oct - 16 Oct
Long Trail House at Stratton Mountain Resort
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

2. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$483
HK$2,470 total
includes taxes & fees
26 Oct - 27 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

3. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is HK$585
HK$1,761 total
includes taxes & fees
26 Oct - 27 Oct
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

4. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is HK$1,146
HK$3,161 total
includes taxes & fees
5 Oct - 6 Oct
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A calm lake with a wooden boat on the shore.

5. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is HK$720
HK$2,321 total
includes taxes & fees
13 Oct - 14 Oct
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

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

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is HK$585
HK$2,009 total
includes taxes & fees
5 Oct - 6 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

7. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (35 reviews)
"Great space, great location!"
United States
Jason S.
The price is HK$1,617
HK$4,106 total
includes taxes & fees
4 Oct - 5 Oct
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

8. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is HK$824
HK$2,839 total
includes taxes & fees
11 Oct - 12 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

9. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Once we got to know the fireplace, it was a wonderful addition to a very cozy cabin. The house felt loved and each different room had different touches of character and magic. We absolutely loved our stay. "
United States
Sarah K.
The price is HK$832
HK$3,325 total
includes taxes & fees
5 Oct - 6 Oct
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A two-story blue house with a porch, surrounded by a garden with orange flowers.

10. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is HK$600
HK$1,200 total
includes taxes & fees
4 Oct - 5 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A living room with a television, sofa, and coffee table.

11. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (5 reviews)
"Host was very accommodating and understanding. Really smooth communication with the host. And the location couldn’t have been much better."
United States
Ernesto M.
The price is HK$1,624
HK$3,839 total
includes taxes & fees
12 Oct - 13 Oct
Long Trail House South Wing 2B2B Condo
Gather around the glowing fire pit and unwind under the open sky, the perfect way to end a day of adventure.

12. Cozy Studio | Ski-In Access + Kitchenette

Cozy Studio | Ski-In Access + Kitchenette
West Dover
10.0 out of 10, Exceptional, (3 reviews)
"Fabulous! Clean, accommodating staff, great amenities, beautiful view, super easy access to skiing! Would def stay here again. "
United States
Kathy S.
The price is HK$1,365
HK$1,724 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Studio | Ski-In Access + Kitchenette
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

13. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
The price is HK$1,096
HK$3,187 total
includes taxes & fees
13 Oct - 14 Oct
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
An indoor swimming pool with a tiled floor, a pool table, and a bar area.

14. Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Dover
9.6 out of 10, Exceptional, (5 reviews)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
The price is HK$1,069
HK$3,389 total
includes taxes & fees
18 Oct - 19 Oct
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
A spacious living area with a red sofa, wooden staircase, and a kitchen with a bar.

15. Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA

Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
Dover
10.0 out of 10, Exceptional, (1 review)
"Incredible views, immaculate, spacious, fully sticked kitchen, great pool and amenities. Easy access with great communication from the host. 10/10 recommend"
United States
Danielle F.
Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
Property grounds

16. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is HK$1,412
HK$1,995 total
includes taxes & fees
6 Oct - 7 Oct
Spacious apartment in beautiful, historic Arlington VT
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

17. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
The price is HK$2,981
HK$6,130 total
includes taxes & fees
15 Oct - 16 Oct
Spacious Vermont Farmhouse 3 Mi to Mount Snow
Wake up to breathtaking mountain views and slopeside convenience at this cozy retreat, where adventure and relaxation go hand in hand.

18. Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is HK$1,467
HK$1,870 total
includes taxes & fees
19 Oct - 20 Oct
Deluxe Studio | Murphy Bed + Sofa
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

19. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is HK$585
HK$2,462 total
includes taxes & fees
4 Oct - 5 Oct
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

20. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is HK$1,491
HK$3,538 total
includes taxes & fees
27 Oct - 28 Oct
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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 Southern Vermont Hotel Reviews

Colonial Motel

Colonial Motel

8/10 Good
"I love these kinds of motor lodges and I want them to keep improving and to succeed."
David 1-night trip
Posted 1 hour ago
Colonial Motel

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