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

Southern Vermont Vacation Rentals

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Check prices for these dates

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

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 CA $106
CA $367 total
includes taxes & fees
Oct 8 - Oct 9
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, (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 CA $165
CA $293 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Home in Pownal VT
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

3. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is CA $102
CA $148 total
includes taxes & fees
Oct 31 - Nov 1
Cozy Vermont Tiny Home Get Away
A bedroom with a bed, bedside tables, a window, and a radiator.

4. 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 CA $221
CA $612 total
includes taxes & fees
Oct 8 - Oct 9
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
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 CA $219
CA $281 total
includes taxes & fees
Oct 13 - Oct 14
The Eagles Wing at The CHM - Private Apartment
A garden with a wooden pergola, purple flowers, and a river view.

6. 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 CA $189
CA $378 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

7. 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
The price is CA $279
CA $799 total
includes taxes & fees
Oct 28 - Oct 29
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is CA $319
CA $941 total
includes taxes & fees
Nov 2 - Nov 3
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

9. 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 CA $280
CA $931 total
includes taxes & fees
Oct 21 - Oct 22
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

10. 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 CA $324
CA $798 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 3 Bedroom Condo in the Heart of Manchester VT
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.

11. 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 CA $282
CA $730 total
includes taxes & fees
Oct 8 - Oct 9
Modern Mount Snow Gnarvana - Steps to Carinthia
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.
The price is CA $467
CA $1,038 total
includes taxes & fees
Nov 1 - Nov 2
Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

13. 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 CA $512
CA $764 total
includes taxes & fees
Oct 18 - Oct 19
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
An aerial view of a house surrounded by a forest with autumn foliage.

14. 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 CA $335
CA $788 total
includes taxes & fees
Oct 28 - Oct 29
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Exterior

15. 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 CA $398
CA $1,009 total
includes taxes & fees
Oct 8 - Oct 9
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A modern two-story house with a front porch, a staircase, and a driveway.

16. 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 CA $376
CA $1,356 total
includes taxes & fees
Oct 14 - Oct 15
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

17. 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 CA $549
CA $1,291 total
includes taxes & fees
Oct 25 - Oct 26
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

18. 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 CA $621
CA $1,497 total
includes taxes & fees
Nov 1 - Nov 2
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

19. 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 CA $659
CA $1,676 total
includes taxes & fees
Oct 8 - Oct 9
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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 CA $590
CA $866 total
includes taxes & fees
Nov 1 - Nov 2
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

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."
KERRY 1-night trip
Posted 10 hours ago
Hideaway Inn Mt. Snow

Find out more about Southern Vermont

Southern Vermont Vacation Homes information

Number of reviews
158
Accommodation
648 Vacation Homes
Lowest Price
CA $148
Highest Price
CA $1,676

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