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Holiday Rentals in Shaftsbury

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Holiday Rentals in 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

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (20)
"Great little quiet and peaceful spot that was still very close to Bennington and Manchester.Neighborhood was good for walks or gravel rides."
The price is €235
includes taxes & fees
8 Sept - 9 Sept
Peaceful Stay at Birds of a Feather Farm & Spa

Schuyler Yacht Basin

3.0 star property
8.6 out of 10, Excellent, (17)
"Great place to stay while visiting the area!"
The price is €170
includes taxes & fees
2 Sept - 3 Sept
Schuyler Yacht Basin

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (227)
"We had an incredible time staying at the cottage and can't wait to visit again sometime! From hiking, sitting on the porch drinking coffee, cooking while listening to music, and enjoying time on the pond, everything about our stay was perfect. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

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

3-bedroom cottage on Cossayuna Lake

7.6 out of 10, Good, (4)
"We had a good time. I was a little disappointed about the pool"
The price is €223
includes taxes & fees
1 Sept - 2 Sept
3-bedroom cottage on Cossayuna Lake

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!

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay."
The price is €496
includes taxes & fees
28 Aug - 29 Aug
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

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.

Mountain Sanctuary Dome Rustic Solitude 5BR

9.6 out of 10, Exceptional, (8)
"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

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 €348
includes taxes & fees
4 Sept - 5 Sept
Florida Mountain Log Cabin!

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

8.4 out of 10, Very good, (25)
"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 €236
includes taxes & fees
1 Sept - 2 Sept
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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, (94)
"We had another wonderful stay despite the weather, thank you for letting us enjoy your beautiful home"
The price is €320
includes taxes & fees
27 Aug - 28 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, (171)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.6 out of 10, Excellent, (56)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

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

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (33)
"Was in town for a race with friends. Great base camp for before and after on an amazing property "
Jacksonville Cabin w/ Wraparound Deck & Views

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

10.0 out of 10, Exceptional, (64)
"We had a "
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
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 Shaftsbury Hotel Reviews

Find out more about Shaftsbury

Find out more about Shaftsbury

Everything you need to know about Shaftsbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shaftsbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Shaftsbury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shaftsbury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shaftsbury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shaftsbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shaftsbury holiday rentals we have selected for you start as low as €170 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shaftsbury rentals

At Expedia, we put the best Shaftsbury holiday 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 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 Shaftsbury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around 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. 

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Shaftsbury?

Yes, there are holiday rentals close to the most popular sights in Shaftsbury, or you can select a more secluded option if you're looking for a relaxing stay. Shaftsbury is known for its coffee shops and mountain views. Make sure you have time to check out the sporting events while you're in the area.

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

Contemporary Berkshire Home with Views of Taconic Golf Course: This holiday home rental outside of 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.

How many holiday rentals are there in Shaftsbury?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Shaftsbury stay.

What can I see and do in Shaftsbury?

Lake Shaftsbury State Park and Howard Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Shaftsbury Historical Society Museum and Robert Frost Stone House Museum.

What are holiday rentals like in Shaftsbury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shaftsbury. Holiday rentals offer extras such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a family getaway.