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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Southern Vermont holiday rentals

A two-story house with a red roof, a front porch with wooden railings, and a gravel driveway.

1. 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 NZ$753
includes taxes & fees
9 Sept - 10 Sept
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

2. 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, (33 reviews)
"Great space, great location!"
United States
Jason S.
The price is NZ$668
includes taxes & fees
9 Sept - 10 Sept
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

3. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (64 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is NZ$428
includes taxes & fees
21 Sept - 22 Sept
Spacious apartment in beautiful, historic Arlington VT
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

4. 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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is NZ$723
includes taxes & fees
10 Sept - 11 Sept
Long Trail House at Stratton Mountain Resort
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

5. 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 NZ$1,370
includes taxes & fees
30 Sept - 1 Oct
Spacious Vermont Farmhouse 3 Mi to Mount Snow
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

6. 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$1,991
includes taxes & fees
18 Sept - 19 Sept
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A living room with a television, sofa, and coffee table.

7. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Very clean accomodations with comfortable beds! Host was very communicative as well!"
United States
carlene p.
The price is NZ$822
includes taxes & fees
16 Sept - 17 Sept
Long Trail House South Wing 2B2B Condo
A man standing at a wooden deck door with wicker furniture and string lights.

8. A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Dover
10.0 out of 10, Exceptional, (21 reviews)
"Excellent location and really fun common spaces made this a great choice for our ski vacation. The hosts were super responsive especially when we got a big snow storm and the driveway was plowed. "
United States
Victoria R.
The price is NZ$997
includes taxes & fees
10 Sept - 11 Sept
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

9. 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.
Walk To Town, Hottub, Firepit, Games, Mt Snow
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

10. 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$1,950
includes taxes & fees
14 Sept - 15 Sept
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

11. 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 NZ$752
includes taxes & fees
9 Sept - 10 Sept
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A spacious kitchen with wooden cabinets, a central island with stools, and a fireplace.

12. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
The price is NZ$1,656
includes taxes & fees
9 Sept - 10 Sept
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
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 NZ$862
includes taxes & fees
14 Sept - 15 Sept
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A two-story log cabin with a balcony on the upper level, surrounded by trees.

14. 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$2,196
includes taxes & fees
9 Sept - 10 Sept
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
A wooden cabin with a patio area featuring Adirondack chairs, a hot tub, and a fire pit.

15. Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Stratton
10.0 out of 10, Exceptional, (6 reviews)
"Everything about our stay was top notch. Highly recommend and I will book this house again. "
United States
samantha b.
The price is NZ$1,207
includes taxes & fees
9 Sept - 10 Sept
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

16. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (28 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is NZ$786
includes taxes & fees
9 Sept - 10 Sept
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A pathway through a forest with autumn leaves and a wooden bridge.

17. 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 NZ$1,067
includes taxes & fees
15 Sept - 16 Sept
Experience Vermont’s Fall Magic at here at the Lemondrop

18. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is NZ$865
includes taxes & fees
9 Sept - 10 Sept
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

19. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is NZ$1,196
includes taxes & fees
15 Sept - 16 Sept
The Birchwood Cabin - Stunning Mountain Views
A kitchen with a marble countertop, a plate of blueberry muffins, a bowl of blueberries, and glasses of orange juice.

20. The MountainTop | Stratton & Mt Snow | Fire Pit

The MountainTop | Stratton & Mt Snow | Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
The price is NZ$973
includes taxes & fees
14 Sept - 15 Sept
The MountainTop | Stratton & Mt Snow | Fire Pit
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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