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

Holiday Homes in Southern Vermont

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Southern Vermont holiday 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 €236
includes taxes & fees
13 Oct - 14 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

2. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (10 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 €189
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
A bedroom with a bed, bedside tables, a window, and a radiator.

3. 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 €473
includes taxes & fees
23 Oct - 24 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

4. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is €97
includes taxes & fees
31 Oct - 1 Nov
Cozy Vermont Tiny Home Get Away
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

5. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is €173
includes taxes & fees
23 Oct - 24 Oct
The Eagles Wing at The CHM - Private Apartment
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is €599
includes taxes & fees
2 Nov - 3 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A garden with a wooden pergola, purple flowers, and a river view.

7. 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 €241
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

8. 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, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

9. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is €506
includes taxes & fees
12 Oct - 13 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
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.
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A modern bathroom with a glass-enclosed shower, a bathtub, a toilet, and a vanity with a sink and mirror.

11. 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, (42 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is €599
includes taxes & fees
25 Oct - 26 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
An aerial view of a house surrounded by a forest with autumn foliage.

12. 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 €491
includes taxes & fees
9 Nov - 10 Nov
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A wooden barrel structure with a staircase and railing, surrounded by a forest.

13. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
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.
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
A modern two-story house with a front porch, a staircase, and a driveway.

14. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is €826
includes taxes & fees
20 Oct - 21 Oct
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

15. 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 €768
includes taxes & fees
28 Oct - 29 Oct
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

16. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is €712
includes taxes & fees
3 Nov - 4 Nov
1812 House, 2 Stays, 1 home
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

17. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Manchester
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."
United States
Greg W.
The price is €518
includes taxes & fees
8 Nov - 9 Nov
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Exterior

18. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is €621
includes taxes & fees
10 Nov - 11 Nov
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

19. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Stratton
10.0 out of 10, Exceptional, (20 reviews)
"Great spot for a large group. "
United States
Brian G.
The price is €1,022
includes taxes & fees
10 Nov - 11 Nov
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
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 €590
includes taxes & fees
10 Nov - 11 Nov
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Great location and staff is AWESOME! Thanks for another pleasant stay!!"
Carey 1-night trip
Posted 10 hours ago
Hampton Inn and Suites Manchester

Find out more about Southern Vermont

Southern Vermont Holiday Homes information

Number of reviews
188
Accommodation
663 Holiday Homes
Lowest Price
€97
Highest Price
€1,022

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