Holiday Rentals in Shaftsbury

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Our top choices for Shaftsbury holiday rentals

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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is €374
includes taxes & fees
14 Apr - 15 Apr
Long Trail House at Stratton Mountain Resort

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is €1,016
includes taxes & fees
7 Apr - 8 Apr
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
3.0 star property
Newfane
The price is €495
includes taxes & fees
26 Mar - 27 Mar
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.0 out of 10, Very good, (2 reviews)
"The was an excellent experience all around! The place is immaculate and exactly as described, stylish and functional for our group of 8. Appreciated the fireplace, flat screens and PacMan. Check in/out instructions clear and communication w owner quick. The location was convenient for skiing Mt Snow. Jax on Tap a great spot right below for dinner and fun- our crew played shuffleboard and pool. Food was delicious! "
United States
Claudia M.
The price is €562
includes taxes & fees
26 Mar - 27 Mar
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (56 reviews)
"We were a group of 11 and we had a great weekend. Comfortable to stay and plenty to do!"
United States
Olivia R.
The price is €645
includes taxes & fees
26 Mar - 27 Mar
Walk To Town, Hottub, Firepit, Games, Mt Snow

Insanely romantic treehouse perched next to a stream and rolling hills.

Insanely romantic treehouse perched next to a stream and rolling hills.
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is €772
includes taxes & fees
30 Mar - 31 Mar
Insanely romantic treehouse perched next to a stream and rolling hills.

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
10.0 out of 10, Exceptional, (2 reviews)
"as advertised."
United States
Joshua G.
The price is €693
includes taxes & fees
26 Mar - 27 Mar
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
Whitingham
10.0 out of 10, Exceptional, (1 review)
"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 €263
includes taxes & fees
26 Mar - 27 Mar
Lake Whitingham & Mount Snow Area Village Apartment

Sowilo Pine House. All-inclusive food and drinks.

Sowilo Pine House. All-inclusive food and drinks.
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"BEAUTIFUL HOME GREAT VIEWS, CLEAN, SPACIOUS, AND A VERY HELPFUL PROPERTY MANAGER. CLOSE TO OUR WEDDING DESTINATION. HAD A WONDERFUL TIME. WOULD HIGHLY RECOMMEND THIS PROPERTY."
United States
diane
The price is €562
includes taxes & fees
29 Mar - 30 Mar
Sowilo Pine House. All-inclusive food and drinks.

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

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Londonderry
8.2 out of 10, Very good, (11 reviews)
"We had a wonderful stay."
United States
Joshua
The price is €483
includes taxes & fees
30 Mar - 31 Mar
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is €427
includes taxes & fees
30 Mar - 31 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.6 out of 10, Exceptional, (5 reviews)
"Great little space"
United States
John
The price is €552
includes taxes & fees
26 Mar - 27 Mar
Romantic Riverbed Treehouse - hot tub & new sauna!

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (61 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
The price is €211
includes taxes & fees
26 Mar - 27 Mar
Spacious apartment in beautiful, historic Arlington VT

Sowilo Retreat All Inclusive Oak House

Sowilo Retreat All Inclusive Oak House
Cambridge
9.0 out of 10, Wonderful, (2 reviews)
"One of the best getaways that I have ever experienced! The food was amazing the service was A and the scenery was absolutely breathtaking. I will definitely be returning!"
United States
Anthony
The price is €562
includes taxes & fees
6 Apr - 7 Apr
Sowilo Retreat All Inclusive Oak House

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
9.8 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is €486
includes taxes & fees
5 Apr - 6 Apr
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

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, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is €267
includes taxes & fees
26 Mar - 27 Mar
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is €233
includes taxes & fees
13 Apr - 14 Apr
The Studio with a View. Bring your dog, too!

7200 sf Villa & Barn on 4 Acre Manchester Estate

7200 sf Villa & Barn on 4 Acre Manchester Estate
Manchester
9.4 out of 10, Exceptional, (13 reviews)
"Check in and communication were super great and easy. The property is absolutely stunning. House is plenty big for group of 10. The house itself is lovely but needs a little tlc in places. Overall a wonderful stay. "
United States
Alex H.
The price is €1,558
includes taxes & fees
26 Mar - 27 Mar
7200 sf Villa & Barn on 4 Acre Manchester Estate

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is €538
includes taxes & fees
2 Apr - 3 Apr
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
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 €273 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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of Shaftsbury is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.