South Shaftsbury Vacation Rentals from CA $88: Short-Term Rentals for 2026

Q: What's the top vacation rental in South Shaftsbury?

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub : Visitors like this South Shaftsbury vacation home rental. It is located in the city center and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a hot tub.

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Our top choices for South Shaftsbury vacation rentals

A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

1. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Hoosick Falls

cory p.

CA $529 total

includes taxes & fees

Nov 9 - Nov 10

A covered porch with wooden beams, a pool, and chairs.

2. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

Bennington

CA $385 total

includes taxes & fees

Nov 19 - Nov 20

A two-story house with a porch, surrounded by trees and snow.

3. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

CA $406 total

includes taxes & fees

Nov 12 - Nov 13

A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

4. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

Woodford

Dana W.

CA $721 total

includes taxes & fees

Nov 9 - Nov 10

A large, white building with a covered porch and stone foundation.

5. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

Bennington

CA $385 total

includes taxes & fees

Nov 8 - Nov 9

A living room with a wooden floor, a central rug, a sofa, a coffee table, and a door with a 'GUEST' sign.

6. Peaceful Cottage Retreat

cambridge

Caleb N.

CA $252 total

includes taxes & fees

Nov 11 - Nov 12

A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

7. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

Dover

Evan C.

CA $496 total

includes taxes & fees

Nov 8 - Nov 9

8. Spacious apartment in beautiful, historic Arlington VT

Arlington

Mike K.

CA $365 total

includes taxes & fees

Nov 8 - Nov 9

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

9. Cozy Home in Pownal VT

Pownal

Jeri R.

CA $272 total

includes taxes & fees

Nov 8 - Nov 9

A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

10. Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

shushan

Susan f.

CA $517 total

includes taxes & fees

Nov 11 - Nov 12

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

11. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Dover

Tania J.

CA $428 total

includes taxes & fees

Nov 8 - Nov 9

A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

12. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

CA $273 total

includes taxes & fees

Nov 9 - Nov 10

A living room with a leather sofa, wooden coffee table, and a dining area with wicker chairs.

13. Little River Cottage

Salem

CA $372 total

includes taxes & fees

Nov 11 - Nov 12

"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

14. New Studio In Town, By the Water

Williamstown

Lydia J.

CA $394 total

includes taxes & fees

Nov 15 - Nov 16

A calm lake with a wooden boat on the shore.

15. Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Scott S.

CA $399 total

includes taxes & fees

Nov 16 - Nov 17

A building with a sign reading 'Fire Tower Restaurant & Tavern.'

16. Fourth-floor Stratton Village studio with valley-view balcony

Stratton

CA $315 total

includes taxes & fees

Nov 8 - Nov 9

17. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

CA $417 total

includes taxes & fees

Nov 8 - Nov 9

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

18. Long Trail House at Stratton Mountain Resort

Stratton

Michael

CA $619 total

includes taxes & fees

Nov 24 - Nov 25

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

19. Long Trail House 368 condo in Stratton Village, walk to the lifts

Stratton

CA $360 total

includes taxes & fees

Nov 8 - Nov 9

A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

20. The Eagles Wing at The CHM - Private Apartment

Dover

Ava M.

CA $177 total

includes taxes & fees

Nov 9 - Nov 10

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Top South Shaftsbury Hotel Reviews

A snow-covered gazebo with a clear view of the surrounding trees and a bright sun in the background.

Harwood Hill Motel

Bennington

10/10 Excellent

mélanie

A large, two-story house with a covered porch and multiple chimneys.

The Four Chimneys Inn

Bennington

10/10 Excellent

Anonymous traveller

A room with wooden paneling, a piano, a chair, and a door leading to another room.

South Shire

Bennington

10/10 Excellent

TROY

A spacious living room with a fireplace, a piano, and a dining area with round tables and chairs.

Knotty Pine

Bennington

10/10 Excellent

Beatrice

A large bed with a headboard, a bedside table with a lamp, a mirror, and a window with curtains.

Inn At Mount Snow

West Dover

10/10 Excellent

marco

A large, snow-covered house with multiple windows and a well-lit porch.

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Joe

A restaurant with tables set for dining, chairs, and a fireplace in the background.

The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

10/10 Excellent

Graeme

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Tanya

An outdoor seating area with Adirondack chairs and potted plants.

Cozy Corner Motel

Williamstown

10/10 Excellent

alain

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

Williamstown Motel

Williamstown

10/10 Excellent

Guy

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

Willows Motel Williamstown

Williamstown

10/10 Excellent

Alexander

A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

Deerfield Valley Inn

West Dover

10/10 Excellent

Shane

Find out more about South Shaftsbury

Everything you need to know about South Shaftsbury 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 South Shaftsbury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 South Shaftsbury vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Shaftsbury vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Shaftsbury. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Shaftsbury vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Shaftsbury vacation rentals we have selected for you start as low as CA $88 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Shaftsbury rentals

At Expedia, we put the best South Shaftsbury 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 South Shaftsbury 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 South Shaftsbury 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 South Shaftsbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in South Shaftsbury?

Yes, we give you a choice of vacation rentals close to well known sights in South Shaftsbury, or you can go with a more remote option if you're looking for relaxation. South Shaftsbury is known for its museums.

What's the top vacation rental in South Shaftsbury?

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub: Visitors like this South Shaftsbury vacation home rental. It is located in the city center and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a selection of games and a hot tub.

What’s there to see and do in South Shaftsbury?

Explore the area and family-friendly sights such as Sugar Shack, or get out into nature at a spot like Lake Shaftsbury State Park. In the larger area, you’ll find Robert Frost Stone House Museum and Park McCullough House.

What’s a vacation rental in South Shaftsbury like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in South Shaftsbury. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips.

South Shaftsbury Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Shaftsbury vacation rentals

1. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

2. West Barn Suite at Hubbell Homestead - Mountain Views & Jetted Tub

3. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

4. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

5. East Barn Suite at Hubbell Homestaead - Mountain Views & Jetted Tub

6. Peaceful Cottage Retreat

7. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

8. Spacious apartment in beautiful, historic Arlington VT

9. Cozy Home in Pownal VT

10. Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

11. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

12. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

13. Little River Cottage

14. New Studio In Town, By the Water

15. Cozy 3 bedroom condo 2.5 miles to Mount Snow

16. Fourth-floor Stratton Village studio with valley-view balcony

17. Downtown | Waterfront | Walk to Shops

18. Long Trail House at Stratton Mountain Resort

19. Long Trail House 368 condo in Stratton Village, walk to the lifts

20. The Eagles Wing at The CHM - Private Apartment

Find vacation rentals that suit your style

Top South Shaftsbury Hotel Reviews

Harwood Hill Motel

10/10 Excellent

Find out more about South Shaftsbury

South Shaftsbury vacation rentals: An excellent choice for every season

How to find incredible deals on South Shaftsbury rentals

Frequently Asked Questions

Can I find vacation rentals in South Shaftsbury?

What's the top vacation rental in South Shaftsbury?

What’s there to see and do in South Shaftsbury?

What’s a vacation rental in South Shaftsbury like?