Photo by Marc Stempel

Dorset Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Dorset vacation rentals

Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
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 ￥59,606
￥74,092 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Long Trail House at Stratton Mountain Resort
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.8 out of 10, Exceptional, (8)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
The price is ￥17,417
￥52,966 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Bromley Retreat
2 bedrooms, desk, free WiFi
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin in Jamaica

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is ￥18,882
￥35,314 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
Exterior
Bear Pass - Mountain View by RedAwning

Vacation Home in Sunderland

Bear Pass - Mountain View by RedAwning
9.6 out of 10, Exceptional, (5)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
United States
Megan G.
The price is ￥39,373
￥106,103 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Bear Pass - Mountain View by RedAwning
Terrace/patio
Mountain Dream Escape

Vacation Home in Sandgate

Mountain Dream Escape
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful location and home! The apartment was beautifully decorated and so cozy. The hot tub was a great place for stargazing! It was wonderful for our anniversary weekend but would also be great for a longer stay.Great communication with hosts and they were super helpful when we had a minor issue with check in."
United States
Morgan C.
The price is ￥27,783
￥82,601 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Mountain Dream Escape
Private kitchen
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Cabin in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is ￥23,251
￥56,530 total
includes taxes & fees
Dec 29 - Dec 30
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Exterior
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Vacation Home in shushan

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
9.6 out of 10, Exceptional, (20)
"Lovely home. Very pet friendly. "
United States
Kimberly D.
The price is ￥35,228
￥58,568 total
includes taxes & fees
Dec 28 - Dec 29
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Private kitchen
The Birchwood Cabin - Stunning Mountain Views

Cabin in Sunderland

The Birchwood Cabin - Stunning Mountain Views
2.0 star property
10.0 out of 10, Exceptional, (2)
"This cabin was everything we could have asked for! Great, peaceful location with a beautiful view. Tastefully decorated and wonderful open concept for kitchen and living room set-up. We really enjoyed the game room downstairs, too. We will definitely be back soon."
United States
Shannon C.
The price is ￥48,361
￥115,190 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Birchwood Cabin - Stunning Mountain Views
Exterior
The Vermont A-Frame Mountain Retreat

Cabin in Winhall

The Vermont A-Frame Mountain Retreat
9.8 out of 10, Exceptional, (26)
"Great home, perfect weekend away at Stratton. Host was great and so was the property"
United States
Kevin M.
The price is ￥47,178
￥92,516 total
includes taxes & fees
Jan 22 - Jan 23, 2026
The Vermont A-Frame Mountain Retreat
2 bedrooms, WiFi, bed sheets
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Vacation Home in Londonderry

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2.0 star property
8.0 out of 10, Very Good, (1)
"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 ￥39,737
￥76,749 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Clock Tower Base Area

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ￥18,475
￥52,493 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
2 bedrooms, free WiFi, bed sheets
ZenBarn: A Quiet Getaway

Vacation Home in Salem

ZenBarn: A Quiet Getaway
10.0 out of 10, Exceptional, (2)
"This was a great spot to stay. The ski mountain was a hour away, but this was far more affordable and the drive to Okemo is lovely."
United States
Casey O.
The price is ￥46,842
￥58,754 total
includes taxes & fees
Jan 1 - Jan 2, 2026
ZenBarn: A Quiet Getaway
Microwave, oven, stovetop
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Chalet in Wardsboro

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is ￥32,880
￥80,678 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Terrace/patio
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Chalet in Wardsboro

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is ￥33,663
￥74,485 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
House, 4 Bedrooms | Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Vacation Home in Arlington

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
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 ￥39,112
￥106,794 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Exterior
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Condo in Cavendish

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
The price is ￥46,842
￥83,416 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Indoor pool, a heated pool
Grand Equinox | 2 Queen Room + Adventure Delights

Apartment in Manchester Village Historic District

Grand Equinox | 2 Queen Room + Adventure Delights
8.0 out of 10, Very Good, (1)
"Yes, but you have to drive to town "
United States
Cathy W.
The price is ￥40,675
￥48,682 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Grand Equinox | 2 Queen Room + Adventure Delights
Outdoor dining
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Chalet in Stratton

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
10.0 out of 10, Exceptional, (5)
"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "
United States
Nicholas D.
The price is ￥53,077
￥114,824 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Fridge, microwave, oven, stovetop
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Vacation Home in Mt Holly

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is ￥38,360
￥99,253 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Condo in Ludlow

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is ￥29,354
￥54,884 total
includes taxes & fees
Jan 12 - Jan 13, 2026
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dorset Hotel Reviews

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant

10/10 Excellent
"Room was well appointed and spacious, clean and comfortable"
ANTHONY 3-night trip
Posted 20 hours ago
The Reluctant Panther Inn and Restaurant

Find out more about Dorset

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

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

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

Frequently asked questions

Are there vacation rentals in Dorset?

Yes, you can find vacation rentals close to popular sights in Dorset, or you can choose a more secluded option if you want a relaxing place to stay. Dorset is known for its parks and theaters.

What are some of the best vacation home rentals that Dorset has to offer?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: Visitors like this Dorset vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Dorset?

With 24 Expedia vacation rentals, you're sure 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 vacation rentals like in Dorset?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Dorset. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.