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Shaftsbury Holiday Rentals

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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, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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TV, fireplace
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.2 out of 10, Wonderful, (15)
"Great location- 10-15min from Stratton, beautiful views, all the amenities. Awesome decor, will definitely be back!"
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Condo, 2 Bedrooms | Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (69)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is NZ$615
includes taxes & fees
4 Jun - 5 Jun
Long Trail House at Stratton Mountain Resort
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (183)
"The barn was spacious and had everything we needed. The property is breathtaking, great location to the town, and Jeff was a great host. Our dogs were welcome, living their best life running around the property, and it was so special to see the mountains and just breathe in the air there. Would love to come back in the warmer weather!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (37)
"Property was incredible. The house was beautiful and enormous. Very comfortable with a group of 22. Pool and hot tub were great."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
TV
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (14)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Property grounds
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (57)
"We loved our stay at the lodge. We had two couples and kids ranging in age from 2 to 12. We did lots of skiing at Bromley but loved having Manchester so close to explore. The pinball arcade was a great rainy day activity for kids! The house was amazing and bigger than we imagined, we were all extremely comfortable. The only thing to mention is the stairs and upstairs loft are a bit scary for little ones. We blocked them with a baby gate and didn’t let the two year old up there, but it was fine...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Oven, stovetop, dishwasher, coffee/tea maker
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (19)
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is NZ$623
includes taxes & fees
31 May - 1 Jun
VT Cabin overlooking the West River and Village
Exterior
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
10.0 out of 10, Exceptional, (11)
"Peter and Becky were fantastic hosts. Their cottage was a home away from home. It is beautifully appointed and perfectly located. I look forward to staying here again on my next trip to Vermont."
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (22)
"Beautiful home, very clean, great hosts"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Property grounds
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
10.0 out of 10, Exceptional, (40)
"This was an amazing property. The beauty of it made for a truly wonderful weekend experience! The initial booking was smooth and effortless. Communication with the host was stellar from start to finish! When we arrived two of the caretakers were on site to greet us. They thanked us for choosing to stay, offered to help with getting settled, and gave us vital advice on preventing bobcats and bears from being attracted. hey even left some farm fresh eggs for us! Our first stop on our setup tour...
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Interior
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.6 out of 10, Good, (40)
"Can't beat the location. We had a great stay."
The price is NZ$469
includes taxes & fees
27 May - 28 May
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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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.

Other types of properties in Shaftsbury you may be interested in

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (923)
"A great place to stay in North Adams. Clean, friendly and located just a couple of miles from an outstanding breakfast restaurant. "
The price is NZ$262
includes taxes & fees
9 Jun - 10 Jun
Hotel Downstreet
Exterior
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (351)
"No thanks"
The price is NZ$344
includes taxes & fees
6 Jun - 7 Jun
The Equinox Golf Resort & Spa
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Shaftsbury holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Shaftsbury. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Shaftsbury. Seeing all the best attractions is bound to make you fall in love with Shaftsbury. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Shaftsbury short-term rentals, that won’t be hard to do.

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?

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub: This highly rated holiday home rental in Shaftsbury is located in the city centre, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games 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 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.

Recent reviews of Shaftsbury properties
Expedia verified reviews