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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Southern Vermont holiday homes

Interior

1. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Great place"
United States
Aidan K.
The price is NZ$412
includes taxes & fees
24 Aug - 25 Aug
Peaceful getaway at birds of a feather
Interior

2. 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 NZ$429
includes taxes & fees
26 Aug - 27 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior detail

3. 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 NZ$1,488
includes taxes & fees
18 Aug - 19 Aug
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Exterior

4. Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.2 out of 10, Wonderful, (27 reviews)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
The price is NZ$1,401
includes taxes & fees
19 Aug - 20 Aug
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Dining

5. 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, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is NZ$927
includes taxes & fees
16 Sept - 17 Sept
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Dining

6. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 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 NZ$344
includes taxes & fees
20 Aug - 21 Aug
Cozy Home in Pownal VT
Outdoor spa tub

7. 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, (40 reviews)
"House was clean and pet-friendly! Great location between Bromley and Stratton!"
United States
Michael I.
The price is NZ$1,102
includes taxes & fees
18 Aug - 19 Aug
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
In-room safe, iron/ironing board, WiFi, bed sheets

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is NZ$1,100
includes taxes & fees
18 Aug - 19 Aug
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Property grounds

9. 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.
The price is NZ$1,095
includes taxes & fees
25 Aug - 26 Aug
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Dining

10. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Awesome home. Had a great time with the family. Owners were easy to get in touch with."
United States
william k.
The price is NZ$1,054
includes taxes & fees
18 Aug - 19 Aug
Summer Escape Near Lakes, Trails & Mt Snow
Property grounds

11. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is NZ$560
includes taxes & fees
24 Aug - 25 Aug
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Terrace/patio

12. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is NZ$1,141
includes taxes & fees
18 Aug - 19 Aug
3 Mi to Mount Snow: Spacious West Dover Home
Coffee/tea maker, fridge, microwave, oven

13. 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 NZ$1,945
includes taxes & fees
18 Aug - 19 Aug
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Exterior

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)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is NZ$848
includes taxes & fees
31 Aug - 1 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Living area

15. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is NZ$744
includes taxes & fees
7 Sept - 8 Sept
Stunning Glass House nestled in the Vermont wilderness!
TV, fireplace, books, music library

16. 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, (12 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is NZ$1,417
includes taxes & fees
24 Aug - 25 Aug
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Property grounds

17. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is NZ$524
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
Coffee/tea maker, fridge, microwave, oven

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 NZ$1,908
includes taxes & fees
9 Sept - 10 Sept
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Smart TV, fireplace, video games, DVD player

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (62 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
The price is NZ$1,270
includes taxes & fees
18 Aug - 19 Aug
Walk To Town, Hottub, Firepit, Games, Mt Snow
Exterior

20. Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay! The location was extremely convenient to the mountain, and the house was clean, comfortable and spacious. We loved all of the seating in the living room, the large fireplace, and cozy hot tub."
United States
Steve M.
The price is NZ$2,158
includes taxes & fees
18 Aug - 19 Aug
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
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 Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The room was very clean. The staff was very helpful. The breakfast was very nice. This was a one night stay returning from further North."
Dorinda 1-night trip
Posted 11 hours ago
Hampton Inn Brattleboro

Find out more about Southern Vermont

Southern Vermont Holiday Homes information

Number of reviews
412
Accommodation
683 Holiday Homes
Lowest Price
NZ$344
Highest Price
NZ$2,158

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