South Shaftsbury Holiday Rentals

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Holiday Rentals in South Shaftsbury

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (221)
"Beautiful property. Very relaxing, secluded. "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is NZ$679
includes taxes & fees
17 July - 18 July
Long Trail House at Stratton Mountain Resort

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (4)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
Contemporary Berkshire Home with Views of Taconic Golf Course

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (81)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

9.0 out of 10, Wonderful, (20)
"Property out and peaceful and quiet. View is great thanks."
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Studio style farm stay

8.8 out of 10, Excellent, (30)
"Quaint room with lots of artistic charm. Convenient location. Well worth it."
Studio style farm stay

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

8.8 out of 10, Excellent, (43)
"We enjoyed our stay at the Blue House. Its size and location cannot be beat when it comes to group trips. We will be back!"
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Reflections of Tranquility- Lakefront Splendor

10.0 out of 10, Exceptional, (2)
"Excellent all around! Loved the location, everything was clean and comfortable. Will definitely stay again! "
Reflections of Tranquility- Lakefront Splendor

Spacious apartment in beautiful, historic Arlington VT

10.0 out of 10, Exceptional, (43)
"Wow this was more than I expected. It was a great way to experience my first Vrbo. Property was conveniently located and easy to find. We had a very lovely stay. "
The price is NZ$359
includes taxes & fees
10 July - 11 July
Spacious apartment in beautiful, historic Arlington VT

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (22)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (62)
"The barn is beautiful and much more spacious than it looks in the photos. The property the barn is on is also beautiful, a short drive from the town center, and also close to cool sites to visit like the Lincoln House and many amazing hiking trains."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

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

10.0 out of 10, Exceptional, (10)
"Husband and i stayed for an overnight get-away. Perfect for relaxing, great views from porch. Great for a couple or small family"
The price is NZ$526
includes taxes & fees
8 July - 9 July
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Luxury Vacation Rental in the Berkshires!

10.0 out of 10, Exceptional, (14)
"Stayed here multiple times and will come back again. Great place to stay…"
Luxury Vacation Rental in the Berkshires!

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (24)
"Great location close to the slopes. Clean and comfortable. Loved the fireplace. "
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (117)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (53)
"Clean, ideal location, great communication."
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (201)
"This location is awesome. Close to town and skiing but we felt like we were secluded in the forest when sitting in the hot tub. We had a great time!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (20)
"Wonderful get away for the week in VT. Place was clean and beautiful, host was very helpful, and views were gorgeous! "
The price is NZ$429
includes taxes & fees
10 July - 11 July
Peaceful Stay at Birds of a Feather Farm & Spa

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (5)
"We enjoyed the quiet and convenience of this location to Mt. Snow. It was clean and well stocked. Host was kind and responsive."
The price is NZ$1,273
includes taxes & fees
8 July - 9 July
The dreamiest place in Southern Vermont!
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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Frequently asked questions

Can I find holiday rentals in South Shaftsbury?

Yes, there are holiday rentals close to the most popular sights in South Shaftsbury, or you can select a more secluded option if you're looking for a relaxing stay. South Shaftsbury is known for its museums.

What are some of the best holiday rentals that South Shaftsbury has to offer?

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!: This holiday home rental outside of South Shaftsbury is located in the mountains, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in South Shaftsbury?

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

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 wider area, you’ll find Robert Frost Stone House Museum and Park McCullough House.

What’s a holiday rental in South Shaftsbury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Shaftsbury. Holiday rentals feature amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for small groups.