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Top Holiday Rentals in South Shaftsbury

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (226)
"Beautiful property. Very relaxing, secluded. "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
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, (82)
"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!

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.4 out of 10, Exceptional, (41)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.6 out of 10, Exceptional, (8)
"The house was clean, nicely decorated, comfortable and all the amenities we needed! "
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Place was super clean. Beds were comfortable. Location was great."
The price is £301
includes taxes & fees
3 Sept - 4 Sept
Florida Mountain Log Cabin!

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.6 out of 10, Excellent, (24)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
The price is £211
includes taxes & fees
24 Aug - 25 Aug
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Mountain Sanctuary Dome Rustic Solitude 5BR

9.8 out of 10, Exceptional, (6)
"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"
Mountain Sanctuary Dome Rustic Solitude 5BR

Reflections of Tranquility- Lakefront Splendor

10.0 out of 10, Exceptional, (3)
"Excellent all around! Loved the location, everything was clean and comfortable. Will definitely stay again! "
Reflections of Tranquility- Lakefront Splendor

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

9.8 out of 10, Exceptional, (93)
"We had another wonderful stay despite the weather, thank you for letting us enjoy your beautiful home"
The price is £277
includes taxes & fees
26 Aug - 27 Aug
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Seasons On Mount Snow - Ski-in/Ski-out

9.8 out of 10, Exceptional, (170)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out

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 £305
includes taxes & fees
25 Aug - 26 Aug
Long Trail House at Stratton Mountain Resort

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

10.0 out of 10, Exceptional, (15)
"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 £243
includes taxes & fees
21 Aug - 22 Aug
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

10.0 out of 10, Exceptional, (52)
"From beginning to end, a great experience:the owners are very responsive throughout the process, check-in and parking was a breeze, condo is great, location is perfect -- right across the street from the village -- we had a wonderful time -- thank you Brandon!!"
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (106)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

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

10.0 out of 10, Exceptional, (63)
"We had a "
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

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

9.0 out of 10, Wonderful, (44)
"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!

Mountains, pond, old barn, hiking trails- quintessential Vermont

9.4 out of 10, Exceptional, (110)
"The accommodations for our week’s vacation were awesome. The home was beautiful, the goats and chickens enjoyed by all, and the views of the autumn foliage from the back porch were amazing. "
Mountains, pond, old barn, hiking trails- quintessential Vermont

Studio style farm stay

8.8 out of 10, Excellent, (31)
"Quaint room with lots of artistic charm. Convenient location. Well worth it."
Studio style farm stay
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

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?

Contemporary Berkshire Home with Views of Taconic Golf Course: This holiday home rental outside of South Shaftsbury offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Bennington College.

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.