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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 AED 274
AED 941 total
includes taxes & fees
26 Oct - 27 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

2. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AED 264
AED 382 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Vermont Tiny Home Get Away
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

3. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AED 544
AED 697 total
includes taxes & fees
23 Oct - 24 Oct
The Eagles Wing at The CHM - Private Apartment
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

4. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is AED 426
AED 753 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Home in Pownal VT
A bedroom with a bed, bedside tables, a window, and a radiator.

5. 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
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is AED 532
AED 1,541 total
includes taxes & fees
21 Oct - 22 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
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.

6. 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 AED 459
AED 1,536 total
includes taxes & fees
21 Oct - 22 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
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, (65 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 AED 483
AED 960 total
includes taxes & fees
26 Oct - 27 Oct
Family Friendly Hilltop House In Putney Vermont
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 AED 760
AED 2,380 total
includes taxes & fees
21 Oct - 22 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

9. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 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 AED 770
AED 1,874 total
includes taxes & fees
8 Nov - 9 Nov
Stunning Glass House nestled in the Vermont wilderness!
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

10. 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 AED 720
AED 2,102 total
includes taxes & fees
21 Oct - 22 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A two-story house with a porch, surrounded by trees and snow.

11. 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.
The price is AED 676
AED 1,421 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
An aerial view of a house surrounded by a forest with autumn foliage.

12. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • 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 AED 742
AED 1,884 total
includes taxes & fees
2 Nov - 3 Nov
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
A wooden barrel structure with a staircase and railing, surrounded by a forest.

13. Dover Mountain Retreat with Hot Tub Near Mt. Snow

Dover Mountain Retreat with Hot Tub Near Mt. Snow
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 AED 1,062
AED 2,512 total
includes taxes & fees
16 Nov - 17 Nov
Dover Mountain Retreat with Hot Tub Near Mt. Snow
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

14. 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 AED 1,212
AED 3,109 total
includes taxes & fees
1 Nov - 2 Nov
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

15. 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, (43 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is AED 725
AED 2,435 total
includes taxes & fees
22 Oct - 23 Oct
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.

16. 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, (2 reviews)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
The price is AED 992
AED 2,262 total
includes taxes & fees
22 Oct - 23 Oct
Cozy 3 Bedroom Condo in the Heart of Manchester VT
Exterior

17. 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, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is AED 1,028
AED 2,600 total
includes taxes & fees
21 Oct - 22 Oct
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A pathway through a forest with autumn leaves and a wooden bridge.

18. 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 AED 1,190
AED 2,416 total
includes taxes & fees
21 Oct - 22 Oct
Experience Vermont’s Fall Magic at here at the Lemondrop
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

19. 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 AED 1,408
AED 2,094 total
includes taxes & fees
21 Oct - 22 Oct
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.
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

20. 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 AED 1,702
AED 4,331 total
includes taxes & fees
21 Oct - 22 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent
"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward setup, especially trying to get into the shower. The tub and shower however seemed completely new. Very nice! The room is quite large and the bed was very comfortable. I’m only 4’10” so it was a high hurdle for me, so I made up the couch bed and slept there. I usually bring a small folding stool but forgot it, so the couch bed was a nice option…it seems to be new and was comfortable. The first night we ate at the hotel restaurant and everything was very tasty, especially the Brussel sprouts and salmon. We were celebrating my husband’s birthday weekend, and brought wine but had to drink from coffee mugs as the hotel is “green” so no cups in the room. We snagged a couple cups from the restaurant for our second night. 😊 Also there’s no mini fridge. We had breakfast twice at 1MTN restaurant, which we highly recommend! Second night we had dinner at “Ten Tables”…their Berkshire Pork Chop was PHENOMENAL. 3rd night we drove down to Wilmington to “The Anchor”…every single thing was delicious! We had a superb weekend!"
Curtis 3-night trip
Posted 11 hours ago
Grand Summit Resort, A Vail Resorts Property

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