Photo by Marc Stempel

Dorset Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Dorset holiday rentals

Pool
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.4 out of 10, Very good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is S$607
includes taxes & fees
26 Jan - 27 Jan, 2026
Long Trail House at Stratton Mountain Resort
Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
Arlington
8.0 out of 10, Very good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
The price is S$876
includes taxes & fees
13 Jan - 14 Jan, 2026
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Interior
Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall
3.0 star property
Bondville
The price is S$1,662
includes taxes & fees
10 Jan - 11 Jan, 2026
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
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 Dorset Hotel Reviews

Toll Road Inn

Toll Road Inn

10/10 Excellent
"Clean and convenient room, good experience."
Mingyang 2-night trip
Posted 4 days ago
Toll Road Inn

Frequently asked questions

Are there holiday rentals in Dorset?

Yes, there are holiday rentals close to the most popular sights in Dorset, or you can select a more secluded option if you're looking for a relaxing stay. Dorset is known for its parks and theatres.

How many holiday rentals are there in Dorset?

With 24 Expedia holiday rentals, you're guaranteed to find just the right place for your Dorset stay.

What can I see and do in Dorset?

Emerald Lake State Park and Green Mountain National Forest are a couple of scenic spots to enjoy the outdoors, whereas Dorset Playhouse is one of the cultural attractions. Other places in town to visit include Dorset Village Public Library and Dorset Historical Society Museum.

What are holiday rentals like in Dorset?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dorset. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.