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

Southern Vermont Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southern Vermont vacation rentals

A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

1. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
$273 nightly
The price is $309
Oct 19 - Oct 20
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

2. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
$199 nightly
The price is $224
Oct 19 - Oct 20
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

3. 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
$227 nightly
The price is $256
Oct 19 - Oct 20
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A calm lake with a wooden boat on the shore.

4. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
$260 nightly
The price is $294
Oct 25 - Oct 26
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

5. 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, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
$391 nightly
The price is $441
Oct 19 - Oct 20
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

6. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
$92 nightly
The price is $104
Nov 2 - Nov 3
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

7. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
$319 nightly
The price is $361
Oct 19 - Oct 20
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A two-story blue house with a porch, surrounded by a garden with orange flowers.

8. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (36 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
$128 nightly
The price is $143
Oct 19 - Oct 20
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A wooden interior with a kitchen, bar area, and dining space.

9. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (7 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$232 nightly
The price is $260
Nov 2 - Nov 3
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

10. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
$254 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

11. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (11 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.
$183 nightly
The price is $205
Oct 20 - Oct 21
Total with taxes and fees
Cozy Home in Pownal VT
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

12. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
$278 nightly
The price is $314
Oct 19 - Oct 20
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

13. 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.
$168 nightly
The price is $190
Oct 23 - Oct 24
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
Wake up to breathtaking mountain views and slopeside convenience at this cozy retreat, where adventure and relaxation go hand in hand.

14. Charming 1BR Retreat | Ski-In Access

Charming 1BR Retreat | Ski-In Access
West Dover
$194 nightly
The price is $214
Nov 2 - Nov 3
Total with taxes and fees
Charming 1BR Retreat | Ski-In Access
A white building with green shutters, a covered porch, and a landscaped garden with flowers.

15. ADA King Room w/ Roll-In Shower & Views

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
$226 nightly
The price is $249
Nov 4 - Nov 5
Total with taxes and fees
ADA King Room w/ Roll-In Shower & Views
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, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$411 nightly
The price is $465
Nov 16 - Nov 17
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A wooden house with a porch lit by string lights, surrounded by snow.

17. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
$393 nightly
The price is $445
Nov 4 - Nov 5
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

18. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
$360 nightly
The price is $406
Oct 19 - Oct 20
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

19. 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, (37 reviews)
"Great space, great location!"
United States
Jason S.
$413 nightly
The price is $467
Oct 19 - Oct 20
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
An indoor swimming pool with a tiled floor, a pool table, and a bar area.

20. Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex

Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
Dover
9.6 out of 10, Exceptional, (5 reviews)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
$382 nightly
The price is $432
Oct 19 - Oct 20
Total with taxes and fees
Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"The vintage property is well maintained. The staff was friendly and informative. Room was comfy and clean. Loved listening to records in our room, and a great selection can be found on each floor. Worth the stay. Would most definitely stay again should I find myself in the area again."
Kelly 1-night trip
Posted 7 hours ago
Latchis Hotel

Find out more about Southern Vermont

Everything you need to know about Southern Vermont vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Vermont vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Vermont vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southern Vermont vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Vermont. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southern Vermont in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $224 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southern Vermont rentals

At Expedia, we put the best Southern Vermont vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southern Vermont rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Vermont vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Vermont. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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