Holiday Homes in Southern Vermont

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Southern Vermont

Our top choices for Southern Vermont holiday homes

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"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 AU$351
includes taxes & fees
16 Sept - 17 Sept
Berkshire Village Carriage House - Super Private!!
Peaceful Stay at Birds of a Feather Farm & Spa
Interior

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 AU$423
includes taxes & fees
24 Aug - 25 Aug
Peaceful Stay at Birds of a Feather Farm & Spa
Cozy motel suite in charming Woodford with WiFi, AC
Interior

Cozy motel suite in charming Woodford with WiFi, AC

The price is AU$212
includes taxes & fees
5 Sept - 6 Sept
Cozy motel suite in charming Woodford with WiFi, AC
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

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 AU$391
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.
Smart TV, fireplace, ping pong

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 AU$690
includes taxes & fees
24 Aug - 25 Aug
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Mt Snow/Stratton Ski Cottage w/ scenic water views
Living area

Mt Snow/Stratton Ski Cottage w/ scenic water views

The price is AU$752
includes taxes & fees
24 Aug - 25 Aug
Mt Snow/Stratton Ski Cottage w/ scenic water views
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

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 AU$466
includes taxes & fees
24 Aug - 25 Aug
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2 bedrooms, WiFi, bed sheets

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

2.0 star property
The price is AU$810
includes taxes & fees
5 Sept - 6 Sept
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203
Interior

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 AU$556
includes taxes & fees
24 Aug - 25 Aug
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203
The Mountain Escape!
Outdoor spa tub

The Mountain Escape!

9.8 out of 10, Exceptional, (18)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is AU$894
includes taxes & fees
22 Sept - 23 Sept
The Mountain Escape!
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
House, 3 Bedrooms | Exterior

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 AU$976
includes taxes & fees
24 Aug - 25 Aug
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Family Friendly Hilltop House In Putney Vermont
Property grounds

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 AU$541
includes taxes & fees
24 Aug - 25 Aug
Family Friendly Hilltop House In Putney Vermont
Alpine 5, cozy Vermont retreat
1 bedroom, desk, iron/ironing board, WiFi

Alpine 5, cozy Vermont retreat

The price is AU$244
includes taxes & fees
2 Sept - 3 Sept
Alpine 5, cozy Vermont retreat
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

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 AU$318
includes taxes & fees
3 Sept - 4 Sept
Charming 1-bedroom condo in delightful Dover
Room 7 - family room sleeps 4
Property grounds

Room 7 - family room sleeps 4

The price is AU$244
includes taxes & fees
15 Sept - 16 Sept
Room 7 - family room sleeps 4
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop

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"
The price is AU$858
includes taxes & fees
15 Sept - 16 Sept
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is AU$1,060
includes taxes & fees
10 Sept - 11 Sept
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Ski in Ski out Condo! Pool access
Terrace/patio

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!"
Ski in Ski out Condo! Pool access
Zen 10, relax and retreat in the heart of Vermont
Property grounds

Zen 10, relax and retreat in the heart of Vermont

The price is AU$244
includes taxes & fees
22 Sept - 23 Sept
Zen 10, relax and retreat in the heart of Vermont
Room 4 - Prickly Pear double room
1 bedroom, desk, iron/ironing board, travel cot

Room 4 - Prickly Pear double room

The price is AU$244
includes taxes & fees
24 Aug - 25 Aug
Room 4 - Prickly Pear double room
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Very nice property with friendly staff; excellent food at the restaurant; was only there for 16 hours but definitely want to go back to stay longer."
Julia 1-night trip
Posted 2 days ago
Kimpton Taconic Hotel by IHG