South Shaftsbury Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for South Shaftsbury vacation rentals

Dining

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
Sowilo Retreat All-Inclusive Cedar House
Fridge, microwave, oven, stovetop

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is ￥73,780
￥187,700 total
includes taxes & fees
May 25 - May 26
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Outdoor spa tub

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 ￥39,999
￥49,719 total
includes taxes & fees
May 25 - May 26
Long Trail House at Stratton Mountain Resort
Outdoor dining

Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is ￥18,051
￥21,585 total
includes taxes & fees
May 25 - May 26
Romantic New York Getaway near the Adirondacks
Smart TV, fireplace, video games, DVD player

Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (44 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
Summer Escape Near Lakes, Trails & Mt Snow
Dining

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 ￥57,114
￥106,886 total
includes taxes & fees
May 25 - May 26
Sowilo Pine House. All-inclusive food and drinks.
Exterior

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)
"Lovely location, well appointed, dog friendly."
United States
Anonymous traveler
The price is ￥28,509
￥55,143 total
includes taxes & fees
May 25 - May 26
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Dining

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 ￥57,114
￥106,886 total
includes taxes & fees
May 25 - May 26
Sowilo Retreat All Inclusive Oak House
Cottage (1 Bedroom) | Interior

< 6 Mi to Arlington: 'whimsical Stone Abode!'

< 6 Mi to Arlington: 'whimsical Stone Abode!'
3.0 star property
Arlington
10.0 out of 10, Exceptional, (1 review)
"We came into town for a few days to visit friends. This was a perfect place. The home was clean and very inviting! Quiet location. Fully stocked kitchen with all the appliances and cooking ware you may need. You will not regret staying here. We loved the photo album of how the home was built! "
United States
Dale
The price is ￥31,199
￥54,702 total
includes taxes & fees
May 25 - May 26
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Smart TV, fireplace, video games, DVD player

Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (59 reviews)
"Great house loved the game room."
United States
Adam B.
The price is ￥39,795
￥110,622 total
includes taxes & fees
May 25 - May 26
Walk To Town, Hottub, Firepit, Games, Mt Snow
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (6 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is ￥37,606
￥65,130 total
includes taxes & fees
May 25 - May 26
The Greylock Cabin
Interior

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Place was great, perfect location, super clean! Owner had coffee k-cups available, single-use toothbrushes, etc. Great weekend!"
United States
Jim D.
The price is ￥36,532
￥97,944 total
includes taxes & fees
May 26 - May 27
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Fridge, microwave, oven, stovetop

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
The price is ￥87,549
￥159,368 total
includes taxes & fees
May 25 - May 26
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Property grounds

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (61 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
The price is ￥30,244
￥42,253 total
includes taxes & fees
Jun 7 - Jun 8
Spacious apartment in beautiful, historic Arlington VT
Fridge, microwave, oven, stovetop

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, (105 reviews)
"The host was very responsive and helpful. The property itself was also fantastic, with plenty of amenities and kept very clean."
United States
Jon
The price is ￥18,481
￥49,489 total
includes taxes & fees
May 31 - Jun 1
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Outdoor pool, a heated pool

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)
The price is ￥10,831
￥51,630 total
includes taxes & fees
May 28 - May 29
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Smart TV

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 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 ￥18,481
￥32,287 total
includes taxes & fees
May 25 - May 26
Cozy Home in Pownal VT
Living area

Green Mountain Getaway

Green Mountain Getaway
Bennington
9.6 out of 10, Exceptional, (18 reviews)
"Very clean property. The location was very convenient to the Main Street of Bennington. Easy check in process. Would definitely stay here again! "
United States
Meredith Y.
The price is ￥32,791
￥65,162 total
includes taxes & fees
May 25 - May 26
Green Mountain Getaway
Exterior

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)
"We had a great family getaway here! The hot tub was amazing and the views from the hot tub were perfect. What a beautiful location - quiet, peaceful and a fun space for kids to explore. We had an amazing time trekking out in the woods in the snow.Kitchen was well stocked and the treats, coffee and tea were a nice bonus. My kids enjoyed the extra games as well! Extremely quick responses from the host as well! Thanks for a good time, we are already thinking about coming back in the summer."
United States
Amanda H.
The price is ￥21,330
￥51,797 total
includes taxes & fees
May 27 - May 28
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Exterior

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is ￥32,234
￥71,211 total
includes taxes & fees
May 25 - May 26
North Getaway Cottage
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"This is one of my favorite hotels. It’s close to restaurants but is also quiet with lots of cozy common space. It’s dog-friendly, has a great social hour and restaurant, and the morning coffee is delicious!"
Erin 2-night trip
Posted 4 hours ago
Kimpton Taconic Hotel by IHG

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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Look no further and take a look at our great range of rental properties in South Shaftsbury!

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.