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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Southern Vermont vacation homes

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

1. 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 ￥11,835
￥40,653 total
includes taxes & fees
Sep 29 - Sep 30
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

2. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is ￥20,003
￥66,733 total
includes taxes & fees
Sep 28 - Sep 29
Modern Mount Snow Gnarvana - Steps to Carinthia
A room with wooden walls, a window with a view of the sky and greenery, a hanging macrame wall decoration, and a vase with flowers on the windowsill.

3. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
Peaceful getaway at birds of a feather
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

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

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (20 reviews)
"Great place!"
United States
Jack & Heather G.
The price is ￥31,115
￥90,835 total
includes taxes & fees
Oct 6 - Oct 7
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A snow-covered wooden cabin with a balcony, surrounded by snow-covered trees.

5. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is ￥37,608
￥108,574 total
includes taxes & fees
Sep 28 - Sep 29
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

6. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (41 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is ￥31,329
￥105,254 total
includes taxes & fees
Oct 19 - Oct 20
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A bedroom with a bed, bedside tables, a window, and a radiator.

7. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is ￥25,375
￥69,676 total
includes taxes & fees
Sep 28 - Sep 29
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ￥16,951
￥30,507 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Home in Pownal VT
A pathway through a forest with autumn leaves and a wooden bridge.

9. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is ￥50,435
￥102,376 total
includes taxes & fees
Sep 26 - Sep 27
Experience Vermont’s Fall Magic at here at the Lemondrop
A two-story house with a porch, surrounded by trees and snow.

10. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is ￥21,114
￥51,658 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
An aerial view of a house surrounded by a forest with autumn foliage.

11. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is ￥40,005
￥91,389 total
includes taxes & fees
Sep 29 - Sep 30
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A wooden barrel structure with a staircase and railing, surrounded by a forest.

12. Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
A red house with a porch, surrounded by a grassy yard and trees.

13. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is ￥19,952
￥63,022 total
includes taxes & fees
Sep 29 - Sep 30
Two Brooks Lodge
A spacious kitchen with a large island, a stone fireplace, and wooden beams.

14. Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley

Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"House was great for our family ski trip! "
United States
Brooke S.
The price is ￥42,545
￥111,400 total
includes taxes & fees
Oct 1 - Oct 2
Views for Days | Hot Tub, Sauna, EV, A/C | 6 Min to Stratton, 15 to Bromley
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

15. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

Spacious Vermont Farmhouse | 3 Mi to Mount Snow
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is ￥50,013
￥128,947 total
includes taxes & fees
Oct 8 - Oct 9
Spacious Vermont Farmhouse | 3 Mi to Mount Snow
A garden with a wooden pergola, purple flowers, and a river view.

16. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is ￥21,146
￥41,820 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

17. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is ￥73,358
￥186,627 total
includes taxes & fees
Oct 8 - Oct 9
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

18. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is ￥51,594
￥133,285 total
includes taxes & fees
Sep 29 - Sep 30
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

19. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (63 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
The price is ￥48,720
￥122,324 total
includes taxes & fees
Sep 29 - Sep 30
Walk To Town, Hottub, Firepit, Games, Mt Snow
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

20. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is ￥65,881
￥96,888 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

8/10 Good
"Yes"
jeffrey 2-night trip
Posted 2 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Southern Vermont

Southern Vermont Vacation Homes information

Number of reviews
317
Accommodation
665 Vacation Homes
Lowest Price
￥30,507
Highest Price
￥186,627

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