South Shaftsbury Vacation Rentals

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.

Dates

November 2026

December 2026

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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.

￥57,355 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Bennington

￥43,215 total

includes taxes & fees

Nov 8 - Nov 9

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.

￥45,955 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.

￥81,556 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

￥42,862 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.

￥27,271 total

includes taxes & fees

Nov 8 - Nov 9

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.

￥56,224 total

includes taxes & fees

Nov 9 - Nov 10

8. Spacious apartment in beautiful, historic Arlington VT

Arlington

Mike K.

￥40,659 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.

￥30,709 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.

￥57,550 total

includes taxes & fees

Nov 8 - Nov 9

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.

￥47,888 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.

￥31,865 total

includes taxes & fees

Nov 8 - Nov 9

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

13. Little River Cottage

Salem

￥41,431 total

includes taxes & fees

Nov 8 - Nov 9

"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.

￥43,956 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.

￥46,093 total

includes taxes & fees

Dec 1 - Dec 2

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

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

Stratton

￥35,431 total

includes taxes & fees

Nov 9 - Nov 10

17. Downtown | Waterfront | Walk to Shops

Williamstown

Douglas

￥47,905 total

includes taxes & fees

Nov 15 - Nov 16

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

￥69,495 total

includes taxes & fees

Nov 9 - Nov 10

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

￥40,058 total

includes taxes & fees

Nov 9 - Nov 10

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.

￥19,932 total

includes taxes & fees

Nov 11 - Nov 12

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Find vacation rentals that suit your style

Top South Shaftsbury Hotel Reviews

An indoor swimming pool with clear water, metal railings, and lounge chairs.

Hampton Inn Bennington

Bennington

10/10 Excellent

Andrrw

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

We stayed here for one overnight while visiting the area. The hotel was just what we were looking for - affordable, clean, great location. There is a restaurant right next door and an apple picking orchard across the street. Easy 5-10 minute drive to a few other restaurants and about 30 minutes from Manchester with great shopping and hiking. The free breakfast in the morning was also great. I would recommend it!

Allison

A hotel reception area with a modern design, featuring a reception desk, seating area, and artwork on the walls.

New Englander Inn Bennington

Bennington

10/10 Excellent

NEIL

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

The Four Chimneys Inn

Bennington

10/10 Excellent

Randall

A hotel room with a large bed, a desk with a chair, a balcony with a view, and a TV mounted on the wall.

Hotel Vervana, Trademark Collection by Wyndham

Bennington

10/10 Excellent

Lisa

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

Anonymous traveler

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

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

A modern living room with a fireplace, large windows, and a cozy seating area.

Inn At Mount Snow

West Dover

10/10 Excellent

Peter

A swimming pool with a view of a barn and mountains in the background.

Hill Farm Inn

Arlington

10/10 Excellent

Michael

A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

The Inn at Ormsby Hill

Manchester Center

10/10 Excellent

The Inn at Ormsby Hill is a magnificent B&B in historic Manchester Vermont. We were in Vermont for a ski week vacation. We ended our trip staying at this Inn and skiing at Stratton Ski Area. When we arrived, the Innkeeper Maryanne greeted us then suggested we move our room to one more centrally located. Our room was beautiful with a 4 post king bed, gas fireplace and plush bathrobes. The daily breakfast was superb! The dining area was full of antiques, many from the Pullman Corporation. Edward...

Anonymous traveler

A wooden sign with an arrow pointing to the right, labeled "CHICKENS".

The Wilmington Inn

Wilmington

10/10 Excellent

Sophia

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Ann

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Stacey

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

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

Brittany Motel

Manchester Center

10/10 Excellent

Heaven

A fire pit with flames, surrounded by outdoor seating and string lights.

Kimpton Taconic Hotel by IHG

Manchester Village Historic District

10/10 Excellent

john

Find out more about South Shaftsbury

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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

Hampton Inn Bennington

10/10 Excellent

Find out more about South Shaftsbury

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?