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Dorset Holiday Rentals

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Holiday Rentals in Dorset

Seven Springs House Nestled in the Heart of Dorset

Seven Springs House Nestled in the Heart of Dorset

1060 Upper Hollow Rd, Dorset, VT
This family-friendly Dorset holiday home is located in a rural location, 2.4 mi (3.9 km) from Dorset Playhouse, and within 9 mi (15 km) of Orvis Fly Fishing ...
Seven Springs House Nestled in the Heart of Dorset
Exceptional Vacation In Dorset 4 Bedroom Home

Exceptional Vacation In Dorset 4 Bedroom Home

3.5 out of 5
78 Songbird Meadows Road, Dorset, VT
Situated in Dorset, this golf holiday home is 1.9 mi (3 km) from Dorset Playhouse and within 9 miles (15 km) of Merck Forest Farmland Center and Dana L. Thompson ...
Exceptional Vacation In Dorset 4 Bedroom Home
Meadow View Cottage- Dorset Historic Village

Meadow View Cottage- Dorset Historic Village

2999 Dorset West Road, Dorset, VT
Situated in Dorset, this holiday home is 0.6 mi (1 km) from Dorset Playhouse and within 9 miles (15 km) of Merck Forest Farmland Center and Dana L. Thompson ...
Meadow View Cottage- Dorset Historic Village
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Newly renovated mountain view close to skiing and horse show

Newly renovated mountain view close to skiing and horse show

1830 Dorset West Rd, Dorset, VT
Situated in the mountains, this holiday home is 1.8 mi (2.9 km) from Dorset Playhouse and within 6 miles (10 km) of Dana L. Thompson Memorial Park and Manchester ...
Newly renovated mountain view close to skiing and horse show
Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen

Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen

78 Song Bird Meadows, Dorset, VT
Situated in Dorset, this holiday home is 1.8 mi (3 km) from Dorset Playhouse and within 9 miles (15 km) of Merck Forest Farmland Center and Dana L. Thompson ...
5/5 Exceptional! (9 reviews)
Great property!
"This home is exactly as it appears in the photos- just a stunning property with magnificent views. The home is cozy and liveable while also having a luxurious feel. Also very well-stocked to prepare meals and serve them. We really enjoyed our stay & would love to come again!"

Reviewed on 25 Jun. 2021

Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd, Stratton, VT
The price is AU$562 per night from 6 Dec. to 6 Dec.
This family-friendly Stratton aparthotel is located in a state park, within 1 mi (2 km) of Stratton Mountain Summit Gondola Ski Lift and Stratton Mountain Resort. ...
4.1/5 Very Good! (41 reviews)
"The property was beautiful. Well maintained and a nice place to walk around. The room was gorgeous, clean and comfortable. We were a little disappointed with the view from our room because when we booked it, the description said it was a “Mountain View” and showed a picture as if we had a slope side ..."

Reviewed on 9 Aug. 2021

Long Trail House at Stratton Mountain Resort
Okemo Mt. Family Affordable 1st floor, Village , Shuttle, walk to town, Dogs OK

Okemo Mt. Family Affordable 1st floor, Village , Shuttle, walk to town, Dogs OK

68 Pleasant ST, Ludlow, VT
This family-friendly Ludlow apartment building is located on the riverfront, within 2 mi (3 km) of Dorsey Park and Okemo Mountain Resort. Jackson Gore Ski Resort ...
4.8/5 Exceptional! (99 reviews)
Wonderful property!
"This is the third time we stayed at 68 Pleasant. I wish we lived there all the time! Perfect for us. Big and spacious and very clean and comfortable! Close to town. So fun! I hated to leave today! 😉"

Reviewed on 7 Nov. 2021

Okemo Mt. Family Affordable 1st floor, Village , Shuttle, walk to town, Dogs OK
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

5 Creaser Court, Ludlow, VT
Situated in the mountains, this holiday home is 0.6 mi (1 km) from Dorsey Park and within 3 miles (5 km) of Okemo Mountain Resort and Jackson Gore Ski Resort ...
4.8/5 Exceptional! (29 reviews)
Pictures don’t do it justice!
"Very clean, great location!"

Reviewed on 19 Mar. 2021

Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base
★ Xtra 10% OFF ★ Walk to Mountain ★ Amenities+ ★ Fireplace

★ Xtra 10% OFF ★ Walk to Mountain ★ Amenities+ ★ Fireplace

771 Stratton Mountain Rd, Unit 271, Stratton, VT
This family-friendly Stratton condo is within 1 mi (2 km) of Stratton Mountain Summit Gondola Ski Lift and Stratton Mountain Resort. Stratton Mountain Golf Course ...
5/5 Exceptional! (6 reviews)
Perfect Accommodations
"The condo is absolutely beautiful. Everything you would need is there. As soon as we walked in, we knew we made the right decision. Cozy and very comfortable. Very close proximity to anything you would need to go. And Brandon was extremely courteous and helpful. We would definitely rent again when ..."

Reviewed on 5 Oct. 2021

★ Xtra 10% OFF ★ Walk to Mountain ★ Amenities+ ★ Fireplace
Okemo and Magic Mountain Family Getaway

Okemo and Magic Mountain Family Getaway

72 Dorman Rd, Andover, VT
Located in the mountains, this family-friendly holiday home is within 6 mi (10 km) of Mill Museum, West River, and Weston Playhouse. Lowell Lake State Park and ...
5/5 Exceptional! (1 review)
Wonderful weekend getaway!
"This was a great place for a weekend getaway with the family. The house was tastefully decorated and had all the amenities we could possibly need. The kitchen was well equipped and allowed us cook great meals. Plenty of space for the kids to play on all three levels while my husband and I could enjoy ..."

Reviewed on 5 Oct. 2021

Okemo and Magic Mountain Family Getaway
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
77 Okemo Ridge Rd, Ludlow, VT
The price is AU$388 per night from 6 Dec. to 6 Dec.
Situated in the mountains, this holiday home is within 1 mi (2 km) of Dorsey Park and Okemo Mountain Resort. Jackson Gore Ski Resort at Okemo is 2.6 mi (4.1 ...
3.4/5 (17 reviews)
"Cozy, clean, quiet."

Reviewed on 20 Jul. 2021

Okemo Mountain Lodging
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
77 Okemo Ridge Rd, Ludlow, VT
The price is AU$450 per night from 6 Dec. to 6 Dec.
Located in the mountains, this Ludlow aparthotel offers ski-in/ski-out access within 3 miles (5 km) of Okemo Mountain Resort, Jackson Gore Ski Resort at Okemo ...
3.6/5 Good! (14 reviews)
"The staff @ Jackson Gore were exceptional! I was completely taken back when I arrived last week for my birthday...as I was unaware I would need a car to get into the town of Ludlow to pick up groceries for my stay in Solitude Village. When I asked Carly @ the front desk about a car service or shuttle ..."

Reviewed on 14 Nov. 2021

Solitude Village at Okemo
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
77 Okemo Ridge Rd, Ludlow, VT
The price is AU$419 per night from 6 Dec. to 6 Dec.
Located in the mountains, this Ludlow aparthotel offers ski-in/ski-out access within 3 miles (5 km) of Okemo Mountain Resort, Jackson Gore Ski Resort at Okemo ...
4.2/5 Very Good! (20 reviews)
Great Week
"We had a great week in this unit. It's just a short walk to the lifts, it was clean and well appointed. I would stay in this unit again"

Reviewed on 31 Mar. 2021

Winterplace at Okemo
Tentrr Signature Site - Grateful Acres Vermont

Tentrr Signature Site - Grateful Acres Vermont

Somerset Road 1584, Wilmington, VT
Situated in the mountains, this campsite is 2.9 mi (4.6 km) from Deerfield River and 3 mi (4.9 km) from Mount Snow. Deerfield River is 2.9 mi (4.6 km) away.
Tentrr Signature Site - Grateful Acres Vermont
Baldwin House, Shrewsbury Vermont

Baldwin House, Shrewsbury Vermont

5159 VT RT 103, Shrewsbury, VT
Located on the riverfront, this family-friendly holiday home is within 12 mi (20 km) of Diamond Run Mall, Vermont State Fairgrounds and Buttermilk Falls. West ...
4.8/5 Exceptional! (32 reviews)
Great old property
"Charming old house, with a great kitchen. The great yard and river were a huge plus! Lots of games in the house too for late nights. Would definitely stay again when we come to town to visit family!"

Reviewed on 20 Oct. 2021

Baldwin House, Shrewsbury Vermont
Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI

Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI

465 Hemlock Hill Rd, Wardsboro, VT
Located in the mountains, this family-friendly cabin is within 12 mi (20 km) of Mount Snow, Stratton Mountain Resort and West River. Secret Passage and Warlock's ...
4.9/5 Exceptional! (46 reviews)
Perfect vacation
"Nice house. Perfect location. No problem at all. Just enjoy my vacation time"

Reviewed on 20 Oct. 2021

Charming Traditional Log Cabin In Between Mt. Snow And Stratton with Sauna/WIFI
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, VT
The price is AU$1,048 per night from 29 Dec. to 29 Dec.
Situated in the mountains, this resort is within 1 mi (2 km) of Stratton Mountain Summit Gondola Ski Lift and Stratton Mountain Resort. Stratton Mountain Golf ...
2.9/5 (12 reviews)
Stratton
"The room was clean and convenient to area activities. Poor communication between vrbo and the lodge made checking in difficult."

Reviewed on 16 Oct. 2021

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts!
Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath

Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath

12 Obertal Rd, Stratton, VT
Set amidst the mountains, this ski-in/ski-out condo in Stratton is within 1 mile (2 km) of Stratton Mountain Summit Gondola Ski Lift and Stratton Mountain Resort, ...
4.8/5 Exceptional! (70 reviews)
Equinox
"Wonderful place and very responsive owner- we had a great stay!"

Reviewed on 12 Aug. 2021

Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath
Condo with a shared seasonal pool & tennis courts - walk to ski trails!

Condo with a shared seasonal pool & tennis courts - walk to ski trails!

38 Trailside Exn, Unit 8E, Ludlow, VT
The price is AU$382 per night from 7 Dec. to 7 Dec.
Located in the heart of Ludlow, this condo is 0.1 mi (0.1 km) from Okemo Mountain Resort and 2.2 mi (3.6 km) from Dorsey Park. Jackson Gore Ski Resort at Okemo ...
4.1/5 Very Good! (18 reviews)
Great ski getaway
"Had a great time for our long weekend. Very clean. Walkable to the slopes would definitely stay again."

Reviewed on 22 Mar. 2021

Condo with a shared seasonal pool & tennis courts - walk to ski trails!
Stratton North Long Trail House Studio Adjacent to the Village and Lifts

Stratton North Long Trail House Studio Adjacent to the Village and Lifts

Stratton, VT
Situated in the mountains, this apartment building is within 1 mi (2 km) of Stratton Mountain Summit Gondola Ski Lift and Stratton Mountain Resort. Stratton ...
4.8/5 Exceptional! (18 reviews)
Great location!
"Great stay, great location. Very helpful property owners!"

Reviewed on 30 Oct. 2021

Stratton North Long Trail House Studio Adjacent to the Village and 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 Dorset you may be interested in

Seven Springs House Nestled in the Heart of Dorset

Seven Springs House Nestled in the Heart of Dorset

1060 Upper Hollow Rd, Dorset, VT
Seven Springs House Nestled in the Heart of Dorset
Exceptional Vacation In Dorset 4 Bedroom Home

Exceptional Vacation In Dorset 4 Bedroom Home

3.5 out of 5
78 Songbird Meadows Road, Dorset, VT
Exceptional Vacation In Dorset 4 Bedroom Home
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 Dorset 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 Dorset. 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 Dorset. Seeing all the best attractions is bound to make you fall in love with Dorset. 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 Dorset short-term rentals, that won’t be hard to do.

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