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South Shaftsbury Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for South Shaftsbury vacation rentals

Terrace/patio

1. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (37 reviews)
"Great place"
United States
Aidan K.
The price is ￥17,708
￥41,342 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful getaway at birds of a feather
Coffee/tea maker, fridge, microwave, oven

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

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (110 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is ￥29,607
￥61,690 total
includes taxes & fees
Aug 4 - Aug 5
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Exterior

3. Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
The price is ￥29,906
￥64,169 total
includes taxes & fees
Aug 22 - Aug 23
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

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

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Exterior

5. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is ￥23,502
￥66,541 total
includes taxes & fees
Aug 4 - Aug 5
Two Brooks Lodge
Dining

6. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (5 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ￥18,274
￥32,454 total
includes taxes & fees
Aug 9 - Aug 10
Cozy Home in Pownal VT
Exterior

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

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (33 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
The price is ￥14,166
￥26,443 total
includes taxes & fees
Aug 6 - Aug 7
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Exterior

8. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is ￥18,180
￥21,674 total
includes taxes & fees
Aug 11 - Aug 12
Romantic New York Getaway near the Adirondacks
Property grounds

9. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (64 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
The price is ￥28,332
￥40,370 total
includes taxes & fees
Aug 16 - Aug 17
Spacious apartment in beautiful, historic Arlington VT
Exterior

10. Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
The price is ￥19,045
￥22,539 total
includes taxes & fees
Aug 4 - Aug 5
Runamuk Farm Camp Tiny House near Cambridge, New York
Lobby

11. 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.
The price is ￥16,527
￥56,949 total
includes taxes & fees
Aug 4 - Aug 5
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Outdoor dining

12. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is ￥18,888
￥42,473 total
includes taxes & fees
Aug 4 - Aug 5
New Studio In Town, By the Water
Exterior

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

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (23 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is ￥28,190
￥55,050 total
includes taxes & fees
Aug 4 - Aug 5
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Property grounds

14. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is ￥29,607
￥53,433 total
includes taxes & fees
Sep 2 - Sep 3
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Beach

15. 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)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is ￥14,166
￥46,244 total
includes taxes & fees
Aug 24 - Aug 25
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Outdoor dining

16. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (9 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is ￥20,462
￥45,503 total
includes taxes & fees
Aug 4 - Aug 5
Downtown | Waterfront | Walk to Shops
Interior

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

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
10.0 out of 10, Exceptional, (1 review)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Smart TV, fireplace, Netflix, streaming services

18. 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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is ￥23,119
￥75,749 total
includes taxes & fees
Sep 1 - Sep 2
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Outdoor dining

19. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (14 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is ￥21,249
￥47,643 total
includes taxes & fees
Aug 5 - Aug 6
2-Bdr Apt In Town, By the Water
Terrace/patio

20. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is ￥43,008
￥109,517 total
includes taxes & fees
Aug 25 - Aug 26
The Birchwood Cabin - Stunning Mountain Views
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 South Shaftsbury Hotel Reviews

Toll Road Inn

Toll Road Inn

10/10 Excellent
"Great place to stay! Rooms are spacious and well maintained. The location is great. We enjoyed exploring the area around the hotel."
Matthew 4-night trip
Posted 4 hours ago
Toll Road Inn

Find out more about South Shaftsbury

Search for holiday rentals in South Shaftsbury on Expedia! You can easily find your home rentals, villas, holiday apartments in South Shaftsbury using one of the methods below:

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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 Bennington College.

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.