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South Shaftsbury Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for South Shaftsbury vacation rentals

Interior

1. Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (38 reviews)
"Laurie was an amazing host, with an amazing property! What an adorable home with an adorable view."
United States
Michaela J.
The price is ￥15,531
￥38,831 total
includes taxes & fees
Sep 22 - Sep 23
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, (114 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 ￥29,509
￥62,182 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Outdoor pool, a heated pool

3. 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.
The price is ￥7,624
￥47,084 total
includes taxes & fees
Sep 20 - Sep 21
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

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

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 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 ￥10,589
￥22,404 total
includes taxes & fees
Sep 20 - Sep 21
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Exterior

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

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 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.
The price is ￥19,767
￥49,643 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Property grounds

6. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (65 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is ￥28,238
￥38,655 total
includes taxes & fees
Sep 21 - Sep 22
Spacious apartment in beautiful, historic Arlington VT
Exterior

7. 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 ￥18,679
￥61,150 total
includes taxes & fees
Sep 20 - Sep 21
Two Brooks Lodge
Exterior

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

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is ￥21,179
￥63,397 total
includes taxes & fees
Sep 21 - Sep 22
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
House (4 Bedrooms) | Interior

9. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
The price is ￥59,614
￥122,573 total
includes taxes & fees
Sep 20 - Sep 21
Spacious Vermont Farmhouse 3 Mi to Mount Snow
Property grounds

10. Amanita Dome. All-inclusive food and drinks.

Amanita Dome. All-inclusive food and drinks.
Cambridge
The price is ￥47,064
￥97,390 total
includes taxes & fees
Sep 20 - Sep 21
Amanita Dome. All-inclusive food and drinks.
Terrace/patio

11. 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 ￥50,151
￥113,098 total
includes taxes & fees
Oct 20 - Oct 21
The Birchwood Cabin - Stunning Mountain Views
Dining

12. Sowilo Retreat All Inclusive Oak House

Sowilo Retreat All Inclusive Oak House
Cambridge
9.0 out of 10, Wonderful, (2 reviews)
"One of the best getaways that I have ever experienced! The food was amazing the service was A and the scenery was absolutely breathtaking. I will definitely be returning!"
United States
Anthony
The price is ￥56,289
￥109,545 total
includes taxes & fees
Sep 21 - Sep 22
Sowilo Retreat All Inclusive Oak House
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, (24 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is ￥28,097
￥54,869 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Dining

14. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 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 ￥16,802
￥29,185 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Home in Pownal VT
Outdoor spa tub

15. 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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is ￥53,148
￥66,065 total
includes taxes & fees
Sep 28 - Sep 29
Long Trail House at Stratton Mountain Resort
Dining

16. Sowilo Retreat All-Inclusive Cedar House

Sowilo Retreat All-Inclusive Cedar House
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"I was looking for a quiet place to deepen my meditation practice, and Sowilo was perfect for that. The hosts were welcoming, and the food was very good. I enjoyed my time in silence and waling through the woods."
United States
Jason
The price is ￥56,289
￥109,719 total
includes taxes & fees
Sep 27 - Sep 28
Sowilo Retreat All-Inclusive Cedar House
Exterior

17. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is ￥18,667
￥22,129 total
includes taxes & fees
Sep 29 - Sep 30
Romantic New York Getaway near the Adirondacks
Exterior

18. 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
The price is ￥11,695
￥35,210 total
includes taxes & fees
Sep 20 - Sep 21
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Interior

19. 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
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is ￥12,001
￥28,477 total
includes taxes & fees
Sep 21 - Sep 22
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Dining

20. Sowilo Pine House. All-inclusive food and drinks.

Sowilo Pine House. All-inclusive food and drinks.
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"BEAUTIFUL HOME GREAT VIEWS, CLEAN, SPACIOUS, AND A VERY HELPFUL PROPERTY MANAGER. CLOSE TO OUR WEDDING DESTINATION. HAD A WONDERFUL TIME. WOULD HIGHLY RECOMMEND THIS PROPERTY."
United States
diane
The price is ￥56,289
￥109,719 total
includes taxes & fees
Sep 23 - Sep 24
Sowilo Pine House. All-inclusive food and drinks.
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

Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"The location was great and rooms were comfortable. What really stood out was the attentiveness and kindness of the entire staff."
Justin 2-night trip
Posted less than an hour ago
Willows Motel Williamstown

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 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.