Southern Vermont Holiday Rentals

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Check prices for these dates

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Southern Vermont holiday rentals

Pool
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is HK$2,959
HK$3,679 total
includes taxes & fees
19 Jan - 20 Jan 2026
Long Trail House at Stratton Mountain Resort
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is HK$1,049
HK$1,976 total
includes taxes & fees
19 Jan - 20 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
2 bedrooms, desk, free WiFi
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin in Jamaica

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is HK$937
HK$1,753 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
Wilmington Retreat Near Trails, Skiing & Festivals
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.8 out of 10, Exceptional, (8)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
The price is HK$864
HK$2,629 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Bromley Retreat
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,088
HK$2,367 total
includes taxes & fees
29 Dec - 30 Dec
Lake Whitingham & Mount Snow Area Village Apartment
Exterior
The Vermont A-Frame Mountain Retreat

Cabin in Winhall

The Vermont A-Frame Mountain Retreat
9.8 out of 10, Exceptional, (26)
"Great home, perfect weekend away at Stratton. Host was great and so was the property"
United States
Kevin M.
The price is HK$2,342
HK$4,592 total
includes taxes & fees
22 Jan - 23 Jan 2026
The Vermont A-Frame Mountain Retreat
Fridge, microwave, oven, stovetop
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Holiday Home in Whitingham

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
10.0 out of 10, Exceptional, (14)
"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 HK$2,044
HK$4,482 total
includes taxes & fees
5 Jan - 6 Jan 2026
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Private kitchen
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Cabin in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is HK$1,154
HK$2,806 total
includes taxes & fees
29 Dec - 30 Dec
Beautiful country cabin with hot tub and outdoor shower in Londonderry
TV, fireplace
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow

Holiday Home in Dover

Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
2.0 star property
9.0 out of 10, Wonderful, (2)
"Weekend stay.Clean, comfortable, well equipped. Was as advertised.I would stay there again"
United States
Noah K.
The price is HK$2,518
HK$5,548 total
includes taxes & fees
13 Jan - 14 Jan 2026
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
Indoor pool, a heated pool
Grand Equinox | 2 Queen Room + Adventure Delights

Apartment in Manchester Village Historic District

Grand Equinox | 2 Queen Room + Adventure Delights
8.0 out of 10, Very good, (1)
"Yes, but you have to drive to town "
United States
Cathy W.
The price is HK$2,019
HK$2,416 total
includes taxes & fees
12 Jan - 13 Jan 2026
Grand Equinox | 2 Queen Room + Adventure Delights
3 bedrooms, iron/ironing board, WiFi, bed sheets
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Apartment in Whitingham

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
10.0 out of 10, Exceptional, (2)
"as advertised."
United States
Joshua G.
The price is HK$3,385
HK$5,645 total
includes taxes & fees
5 Jan - 6 Jan 2026
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Holiday Home in Arlington

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
8.0 out of 10, Very good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
The price is HK$1,963
HK$5,329 total
includes taxes & fees
13 Jan - 14 Jan 2026
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Interior
Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Cottage in Bondville

Stratton Mtn Ski Chalet w/ Giant Views in Winhall
3.0 star property
The price is HK$6,178
HK$10,064 total
includes taxes & fees
9 Jan - 10 Jan 2026
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Exterior
Bear Pass - Mountain View by RedAwning

Holiday Home in Sunderland

Bear Pass - Mountain View by RedAwning
9.6 out of 10, Exceptional, (5)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
United States
Megan G.
The price is HK$1,954
HK$5,015 total
includes taxes & fees
13 Jan - 14 Jan 2026
Bear Pass - Mountain View by RedAwning
Outdoor dining
Green Mountain Getaway

Apartment in Bennington

Green Mountain Getaway
2.0 star property
9.6 out of 10, Exceptional, (18)
"Very clean property. The location was very convenient to the Main Street of Bennington. Easy check in process. Would definitely stay here again! "
United States
Meredith Y.
The price is HK$1,441
HK$2,901 total
includes taxes & fees
4 Jan - 5 Jan 2026
Green Mountain Getaway
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is HK$1,267
HK$3,550 total
includes taxes & fees
21 Jan - 22 Jan 2026
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
2 bedrooms, WiFi, bed sheets
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Holiday Home in Londonderry

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2.0 star property
8.0 out of 10, Very good, (1)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is HK$1,972
HK$3,809 total
includes taxes & fees
5 Jan - 6 Jan 2026
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Smart TV, fireplace
Vermont Vacation Villa—Grapevine Getaway

Villa in Pownal

Vermont Vacation Villa—Grapevine Getaway
9.4 out of 10, Exceptional, (3)
"The villa was great! The house is very spacious and clean. We really enjoyed our stay!"
United States
Jenna S.
The price is HK$3,660
HK$7,520 total
includes taxes & fees
6 Jan - 7 Jan 2026
Vermont Vacation Villa—Grapevine Getaway
Outdoor spa tub
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Holiday Home in Wilmington

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
10.0 out of 10, Exceptional, (53)
"We were a group of 11 and we had a great weekend. Comfortable to stay and plenty to do!"
United States
Olivia R.
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun 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

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

10/10 Excellent
"Ski slopes were accessible and pool was really nice. "
Claudia 7-night trip
Posted 1 day ago
Mount Snow Grand Summit Resort

Find out more about Southern Vermont

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