South Shaftsbury Vacation Rentals

Vacation Rentals in South Shaftsbury

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (69)
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is $317
$384 total
includes taxes & fees
Jun 12 - Jun 13
Long Trail House at Stratton Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (185)
"Lovely, very private property that feels far away and yet is super convenient to Manchester. Great host … everything was easy."
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
8.8 out of 10, Excellent, (38)
"The home location, layout were awesome. Pics must be older as there was maintenance needed on the basketball/tennis court, pool, and shuffleboard room. Our bachelor party had a good time, once some updates are done, could be a 5 start spot."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Property grounds
Stratton South Long Trail Studio Adjacent to the Village and Lifts
9.4 out of 10, Exceptional, (56)
"Right across the road from Stratton Mountain. Check in was easy. Place was clean and comfortable. Much nicer and roomier than a typical hotel room. Highly recommended"
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Vermont house in stunning private country setting and 360 degree panoramic views
Exterior
Vermont house in stunning private country setting and 360 degree panoramic views
10.0 out of 10, Exceptional, (4)
"The property was located in a very picturesque location wth beautiful views all around. We enjoyed the fireplace inside as well as the firepit outside. The country home had everything we needed."
Vermont house in stunning private country setting and 360 degree panoramic views
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Interior
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (8)
"Beautiful property! Responsive and helpful hosts. Short walk into downtown Bennington. We had a blast!"
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Property grounds
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, (194)
"Great all around, would book again"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wilmington Vacation Rental Near Hiking and Skiing!
TV, fireplace, books
Wilmington Vacation Rental Near Hiking and Skiing!
10.0 out of 10, Exceptional, (9)
"Beatiful weekend get away."
Wilmington Vacation Rental Near Hiking and Skiing!
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Fridge, microwave, oven, stovetop
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Fridge, microwave, oven, stovetop
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
10.0 out of 10, Exceptional, (101)
"We were looking for a quick getaway to Vermont and this gorgeous home was perfect! The views are every bit as spectacular as the photos. The home is clean and modern with stunning views of the mountains from the kitchen, living room, and back deck. The living room is large and comfortable for gathering. The adjoining kitchen is clean, modern, and has everything you need to cook a meal or just prepare a quick snack. There are dishes and cooking supplies available, which made meal prep a breeze....
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Fridge, microwave, oven, stovetop
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very Good, (19)
"We had a large crew and this house had plenty of room for all. Large table and lots of room to hang out. The location to the mountain is great- so close! You can walk through the snow to a restaurant. Unfortunately, the new pool was not ready yet, but it looks like it will be gorgeous and we would come back again."
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (39)
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
The price is $229
$611 total
includes taxes & fees
Jun 6 - Jun 7
Mount Snow's Best View - Sleeps 8-10
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (19)
"Good Condo in a great location"
The price is $74
$336 total
includes taxes & fees
Jun 5 - Jun 6
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Walk to Mount Snow, Cozy, Clean and Comfortable!
Pool
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, (28)
"Overall property was good, and the unit was very good. Our needs were minimal, but if we had questions, Tiago was very quick and to respond."
Walk to Mount Snow, Cozy, Clean and Comfortable!
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See all available properties in South Shaftsbury
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.

Other types of properties in South Shaftsbury you may be interested in

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
The Equinox Golf Resort & Spa
Exterior
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (353)
"No thanks"
The price is $143
$207 total
includes taxes & fees
Jun 17 - Jun 18
The Equinox Golf Resort & Spa
The Williams Inn
Front of property - evening/night
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (297)
"Love the Williams Inn"
The price is $254
$284 total
includes taxes & fees
Jun 10 - Jun 11
The Williams Inn
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.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit South Shaftsbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $74 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 spa tub.

How many vacation rentals are there in South Shaftsbury?

Choose from 3 Expedia vacation rentals in South Shaftsbury for a memorable vacation.

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 Mount Equinox. 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.

Recent reviews of South Shaftsbury properties
Expedia verified reviews

Toll Road Inn

Toll Road Inn

5/5 Excellent
"The hotel was so cute!! Very small hotel, very quiet and it was amazing that the windows in the rooms opened for fresh air. The backyard area, pool and hot tub were extremely clean. Very cute sitting area with games and books and a fireplace in the winter. Will absolutely be booking again in the future! "
A verified traveler stayed at Toll Road Inn
Posted 2 days ago
Toll Road Inn