A mountainous landscape with autumn foliage, a prominent church spire, and a winding road.

Shaftsbury Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Shaftsbury holiday rentals

A living room with a wooden floor, a central rug, a sofa, a coffee table, and a door with a 'GUEST' sign.

1. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
The price is HK$981
HK$1,490 total
includes taxes & fees
18 Oct - 19 Oct
Peaceful Cottage Retreat
Property grounds

2. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
The price is HK$1,519
HK$2,132 total
includes taxes & fees
21 Oct - 22 Oct
Spacious apartment in beautiful, historic Arlington VT
A bedroom with a bed, bedside tables, a window, and a radiator.

3. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is HK$1,238
HK$3,399 total
includes taxes & fees
19 Oct - 20 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

4. 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, (116 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is HK$1,476
HK$3,102 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

5. 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)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$483
HK$2,470 total
includes taxes & fees
20 Oct - 21 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A small cabin with a wooden deck, a front door, and large windows.

6. Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"Phenomenal site, with stunning views. Highly recommend!"
United States
Jess M.
The price is HK$984
HK$1,158 total
includes taxes & fees
16 Oct - 17 Oct
Runamuk Farm Camp Tiny House near Cambridge, New York
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

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

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (24 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is HK$1,406
HK$2,745 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A wooden deck leading to a cabin with a pitched roof and large windows.

8. Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is HK$939
HK$1,114 total
includes taxes & fees
18 Oct - 19 Oct
Romantic New York Getaway near the Adirondacks
A two-story house with a porch, surrounded by trees and snow.

9. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"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.
The price is HK$1,287
HK$2,861 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

10. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is HK$824
HK$2,839 total
includes taxes & fees
24 Oct - 25 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A two-story blue house with a porch, surrounded by a garden with orange flowers.

11. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (36 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is HK$600
HK$1,200 total
includes taxes & fees
19 Oct - 20 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A calm lake with a wooden boat on the shore.

12. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is HK$785
HK$2,403 total
includes taxes & fees
8 Nov - 9 Nov
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

13. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (10 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is HK$911
HK$1,609 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

14. 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
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is HK$1,000
HK$3,658 total
includes taxes & fees
19 Oct - 20 Oct
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A bedroom with a bed, a window, and a door.

15. Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
9.0 out of 10, Wonderful, (26 reviews)
"Love this place and the ease of the check in and check out! Quiet and peaceful! Would have like to seen the pub open though! See you all next year!"
United States
Jean Paul
The price is HK$1,335
HK$1,743 total
includes taxes & fees
18 Oct - 19 Oct
Schuyler Yacht Basin
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

16. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
The price is HK$898
HK$3,143 total
includes taxes & fees
3 Nov - 4 Nov
Historic Home with Colonial Charm in Manchester
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

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

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is HK$585
HK$2,480 total
includes taxes & fees
18 Oct - 19 Oct
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

18. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is HK$585
HK$1,770 total
includes taxes & fees
29 Oct - 30 Oct
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

19. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is HK$585
HK$2,010 total
includes taxes & fees
20 Oct - 21 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A spacious living area with a red sofa, wooden staircase, and a kitchen with a bar.

20. Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA

Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
Dover
10.0 out of 10, Exceptional, (1 review)
"Incredible views, immaculate, spacious, fully sticked kitchen, great pool and amenities. Easy access with great communication from the host. 10/10 recommend"
United States
Danielle F.
The price is HK$7,848
HK$11,618 total
includes taxes & fees
18 Oct - 19 Oct
Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
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

The Manchester View

The Manchester View

10/10 Excellent
"Staff was so sweet and accommodating and we really enjoyed the delicious breakfast in the morning. We will definitely return!"
Janee 1-night trip
Posted 14 hours ago
The Manchester View

Find out more about Shaftsbury

Search for holiday rentals in Shaftsbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Shaftsbury using one of the methods below:

  • View our selection of featured holiday rentals in Shaftsbury
  • Use the map to find apartments and other holiday homes in the Shaftsbury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shaftsbury while they last

Look no further and take a look at our great range of rental properties in Shaftsbury!

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?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This holiday home rental outside of Shaftsbury is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 Maple Hill 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.