Holiday Homes in Southern Vermont

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Featured Holiday Homes in Southern Vermont and around

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (255)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is €196
includes taxes & fees
16 Sept - 17 Sept
Berkshire Village Carriage House - Super Private!!

Charming 1-bedroom condo in delightful Dover

10.0 out of 10, Exceptional, (1)
"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "
The price is €177
includes taxes & fees
6 Sept - 7 Sept
Charming 1-bedroom condo in delightful Dover

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is €498
includes taxes & fees
1 Sept - 2 Sept
The Mountain Escape!

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (20)
"Great little quiet and peaceful spot that was still very close to Bennington and Manchester.Neighborhood was good for walks or gravel rides."
The price is €235
includes taxes & fees
25 Aug - 26 Aug
Peaceful Stay at Birds of a Feather Farm & Spa

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is €218
includes taxes & fees
24 Aug - 25 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

10.0 out of 10, Exceptional, (4)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is €383
includes taxes & fees
18 Aug - 19 Aug
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

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. "
The price is €557
includes taxes & fees
18 Aug - 19 Aug
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
The price is €434
includes taxes & fees
25 Aug - 26 Aug
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Cozy motel suite in charming Woodford with WiFi, AC

The price is €119
includes taxes & fees
24 Aug - 25 Aug
Cozy motel suite in charming Woodford with WiFi, AC

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is €251
includes taxes & fees
6 Sept - 7 Sept
Family Friendly Hilltop House In Putney Vermont

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is €277
includes taxes & fees
20 Aug - 21 Aug
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

10.0 out of 10, Exceptional, (12)
"Great property, plenty of space and room for all. Location is ideal"
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

10.0 out of 10, Exceptional, (1)
"We stayed here for one night to ski at Mount Snow and it was amazing! Very comfortable, cozy, well kept, clean with well stocked kitchen. It was perfect for our purpose and would definitely come back!! "
The price is €312
includes taxes & fees
18 Aug - 19 Aug
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is €590
includes taxes & fees
10 Sept - 11 Sept
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"Amazing stay. Perfect weekend friend getaway"
The price is €498
includes taxes & fees
24 Aug - 25 Aug
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

Stunning Glass House nestled in the Vermont wilderness!

10.0 out of 10, Exceptional, (1)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
The price is €425
includes taxes & fees
1 Sept - 2 Sept
Stunning Glass House nestled in the Vermont wilderness!

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is €456
includes taxes & fees
9 Sept - 10 Sept
Ski in Ski out Condo! Pool access

Modern Chic Cabin near Mount Snow

The price is €453
includes taxes & fees
1 Sept - 2 Sept
Modern Chic Cabin near Mount Snow

Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking

10.0 out of 10, Exceptional, (20)
"Super nice place (very clean and modern) in a quiet area."
The price is €356
includes taxes & fees
18 Aug - 19 Aug
Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking
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