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Holiday Rentals in Shaftsbury

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Our top choices for Shaftsbury holiday rentals

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, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is €222
includes taxes & fees
12 Jan - 13 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (28)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is €127
includes taxes & fees
23 Dec - 24 Dec
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
Londonderry
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is €315
includes taxes & fees
24 Dec - 25 Dec
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
2.0 star property
Jamaica
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is €197
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
The price is €365
includes taxes & fees
22 Jan - 23 Jan 2026
Cozy Bromley Retreat

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is €268
includes taxes & fees
5 Jan - 6 Jan 2026
Lake Whitingham & Mount Snow Area Village Apartment

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is €353
includes taxes & fees
5 Jan - 6 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

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, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is €430
includes taxes & fees
5 Jan - 6 Jan 2026
Long Trail House at Stratton Mountain Resort

Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
Mountain Chalet mins from Mt Snow Skiing/hiking

Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (47)
"Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in "
United States
Victor L.
The price is €165
includes taxes & fees
21 Jan - 22 Jan 2026
Peaceful Cottage Retreat

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is €444
includes taxes & fees
13 Jan - 14 Jan 2026
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Sowilo Retreat All-Inclusive Maple House

Sowilo Retreat All-Inclusive Maple House
Cambridge
10.0 out of 10, Exceptional, (1)
The price is €464
includes taxes & fees
23 Dec - 24 Dec
Sowilo Retreat All-Inclusive Maple House

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is €321
includes taxes & fees
5 Jan - 6 Jan 2026
Florida Mountain Log Cabin

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, (34)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is €269
includes taxes & fees
14 Jan - 15 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow

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, (100)
"Quiet and relaxing property "
United States
Michelle S.
The price is €272
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is €426
includes taxes & fees
20 Jan - 21 Jan 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
10.0 out of 10, Exceptional, (2)
"We had a great stay. The cabin was well lit and perfect for two people. Very clean, warm, and comfortable. There was a snow storm the night before we left and they kept the driveway plowed for us. Gorgeous views and close to everything."
United States
Karen L.
The price is €560
includes taxes & fees
12 Jan - 13 Jan 2026
Romantic Riverbed Treehouse - hot tub & new sauna!

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
The price is €628
includes taxes & fees
28 Dec - 29 Dec
Wilmington Retreat Near Trails, Skiing & Festivals
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

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 €390 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. 

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?

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : This holiday home rental outside of Shaftsbury is located in the mountains, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 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 1 hot tub.

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 popular places to visit in the area include Mount Snow and Stratton Mountain Resort.

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.