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Our top choices for Dorset holiday homes

A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

A rustic kitchen with wooden cabinets, a bar area, and a fireplace.

A large house with a driveway, surrounded by lush green trees and a mountain in the background.

A spacious kitchen with a large island, wooden cabinets, and a dining area with a piano.

1. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home

Manchester

The price is £542

£542

includes taxes & fees

3 Nov - 4 Nov

1812 House, 2 Stays, 1 home

A room with a large window, a wooden table, two chairs, and a woven basket on the table.

A deck with outdoor furniture, a view of houses, and a mountain in the background.

A house with a red door, a welcome sign, and a number 94 on the wall.

A dining area with a wooden table and chairs, a chandelier, and a window with blinds.

2. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT

Manchester

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Beautiful place Very spacious and super organized we love our stay "

Rafael

The price is £467

£467

includes taxes & fees

19 Oct - 20 Oct

Cozy 3 Bedroom Condo in the Heart of Manchester VT

A two-story white house with a front porch, a door with a wreath, and a chimney.

A living room with a beige sofa, a light grey armchair, a patterned rug, two windows with blinds, and a small table with a lamp and a tissue box.

A dining area with a wooden table, six chairs, a patterned rug, and a wall-mounted light fixture.

A kitchen with dark wooden cabinets, stainless steel appliances, a window with blinds, and a wooden floor.

3. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Manchester

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "

Marissa H.

The price is £556

£556

includes taxes & fees

24 Oct - 25 Oct

Cozy farmhouse in Manchester - short drive to multiple ski mountains!

An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

A dining area with a wooden table and chairs, a window with a view, and a framed picture on the wall.

A modern kitchen with stainless steel appliances, a tiled backsplash, and a window providing natural light.

A street view at dusk with a restaurant and a shop with a mannequin in the window.

4. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Manchester

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."

Greg W.

The price is £408

£408

includes taxes & fees

22 Oct - 23 Oct

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

A wooden interior with a kitchen area, bar stools, and a dining table.

A modern kitchen with wooden paneling, white cabinets, and a black countertop.

A cozy cabin interior with a wooden interior, a fireplace, a sofa, a dining table, and large windows.

5. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall

9.4 out of 10, Exceptional, (43 reviews)

9.4/10

Exceptional

(43 reviews)

"Our family had a wonderful vacation. The house and location were great. We will come back."

Victoria L.

The price is £482

£482

includes taxes & fees

19 Oct - 20 Oct

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

A building with a sign that reads 'Long Trail House.'

A bedroom with a bed, a lamp, a television, and a window with a view of a snowy landscape.

A pool area with two hot tubs and a brick patio.

6. 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 £199

£199

includes taxes & fees

19 Oct - 20 Oct

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

A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

A cozy room with a wood-burning stove, a chair, a bench, and a Christmas tree.

A rustic kitchen with wooden beams, a dining table with chairs, a chandelier, and a view of the outdoors through large windows.

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, (25 reviews)

9.6/10

Exceptional

(25 reviews)

"Great cabin , so cozy with the wood burning stove "

Susan f.

The price is £265

£265

includes taxes & fees

19 Oct - 20 Oct

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

A living room with a brick fireplace, a sofa, a chair, and a coffee table.

A wooden tub with a wooden spoon resting on a grassy area near a pond, with a wooden structure in the background.

A modern interior with a staircase, a dining area, and a living space with a fireplace.

A wooden birdhouse with a door and a small porch, situated near a pond surrounded by trees.

8. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Clean, lots of room, easy access to Stratton, responsive host."

Mark H.

The price is £621

£621

includes taxes & fees

20 Oct - 21 Oct

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

A bunk bed room with a small table and a door labeled 'Ranger House'.

Green landscapes and tranquil waters right outside

A room with a stone fireplace, wooden ceiling, and a window with curtains.

9. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Ludlow

The price is £338

£338

includes taxes & fees

29 Oct - 30 Oct

Peaceful Stay w/ Pond & Massage Chair | Near Okemo

A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

A bedroom with a wooden ceiling, a bed with a white and blue quilt, two bedside tables with lamps, and a chair.

A cozy room with a leather sofa, a recliner, and a small table. Large windows offer a view of the outdoors.

A covered deck with outdoor seating and a barbecue grill.

10. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly

9.8 out of 10, Exceptional, (42 reviews)

9.8/10

Exceptional

(42 reviews)

"This house has great hang out space and plenty of space for a big family!"

Cheri V.

The price is £378

£378

includes taxes & fees

18 Oct - 19 Oct

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

A two-story house with a covered porch and a garage.

Wrap around porch with access from the kitchen and living area

A room with a large window, a round rug, two plaid chairs, and a kitchen area with cabinets.

A modern kitchen with a central island, bar stools, pendant lighting, and a brick backsplash.

11. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Mount Holly

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "

Chi L.

The price is £621

£621

includes taxes & fees

18 Oct - 19 Oct

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

A rustic kitchen with wooden beams, a large island, and a woman cooking.

A rustic room with a large wood-burning stove, wooden walls, a guitar, and a plaid blanket on the floor.

A rustic barn-style building with a covered porch, a fire pit, and a stack of firewood.

12. Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Londonderry

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"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. "

Christine M.

The price is £371

£371

includes taxes & fees

27 Oct - 28 Oct

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

A cozy living room with a fireplace, comfortable seating, and a television.

A wooden deck with a metal railing, a hanging bird feeder, and a view of a grassy yard with trees.

A wooden interior with a pool table, a sofa, and a dining area.

A bar area with wooden flooring, a trash can, and bar stools.

13. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Ludlow

The price is £296

£296

includes taxes & fees

19 Oct - 20 Oct

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

A spacious wooden cabin with a high ceiling, large windows, a dining area, and a cozy living room.

A spacious loft-style room with a high ceiling and wooden beams, featuring a large seating area with sofas and a dining table.

A wooden cabin with large windows and a deck, surrounded by snow.

14. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Londonderry

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."

Tim M.

The price is £924

£924

includes taxes & fees

3 Nov - 4 Nov

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A two-story house with a porch, a white picket fence, and a small garden with flowers.

A living room with a flat-screen TV, a sofa, a coffee table, and a lamp.

A two-story house with a porch, a white picket fence, and a tree in front.

15. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow

9.8 out of 10, Exceptional, (114 reviews)

9.8/10

Exceptional

(114 reviews)

"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."

Tina l.

The price is £382

£382

includes taxes & fees

15 Nov - 16 Nov

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

16. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very nice stay. Owners were very gracious. House was clean & comfortable."

Lorraine C.

The price is £541

£541

includes taxes & fees

19 Oct - 20 Oct

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

A living room with a sofa, ottoman, and a fireplace.

A kitchen with a Bosch dishwasher, wooden cabinets, a large window with a forest view, and a tiled backsplash.

A loft-style room with a wooden dining table, a sofa, and a large window with a view of trees.

17. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Jamaica

8.8 out of 10, Excellent, (8 reviews)

8.8/10

Excellent

(8 reviews)

"Beautiful home, we enjoyed our stay!"

Luke B.

The price is £446

£446

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

A two-story blue house with a sloped roof, a front porch, and a deck.

A modern living room with a dark gray sectional sofa, a round wooden coffee table, and a patterned rug.

A wooden deck with a sofa and table, a house with white siding, and a clear sky.

18. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"

Tara

The price is £448

£448

includes taxes & fees

19 Oct - 20 Oct

New Ludlow Village Home with Stunning Okemo Mountain View

A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

A two-story house with a wooden porch, stone steps, and a brown door.

A spacious living room with a staircase, a fireplace, and a cozy seating area.

A two-story house with a covered porch, a staircase leading to a deck, and a gravel driveway.

19. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

Stratton

10.0 out of 10, Exceptional, (20 reviews)

10/10

Exceptional

(20 reviews)

"Great spot for a large group. "

Brian G.

The price is £800

£800

includes taxes & fees

20 Oct - 21 Oct

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

A spacious living area with a fireplace, a dining area, and a kitchen.

A hotel room with two beds, a mural of mountains, a window with a view of trees, and a cable car on the wall.

A modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

A modern kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and pendant lighting.

20. Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Ludlow

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"My family and I stayed at this property last weekend and it was amazing!!! We were the first to rent as this is a brand new construction home. Everything inside is brand new from the bedding, furniture and amazing cookware. This house has a few great features that make it top notch: 1: Every bedroom has an en-suite bathroom, so we all had our own space and privacy. The bedrooms were big and beds were so comfortable. The master bedroom has this huge shower and tub that was so nicely designed. 2:...

Michael

The price is £1,654

£1,654

includes taxes & fees

19 Oct - 20 Oct

Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

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

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"Beautiful place"

Amber 1-night trip

Posted 4 hours ago

Jackson Gore Village, A Vail Resorts Property

Hampton Inn and Suites Manchester

10/10 Excellent

"Staff very friendly. Location was a plus. Room clean with comfortable bed."

Kevin 1-night trip

Posted 4 hours ago

Hampton Inn and Suites Manchester

Sun Lodge near Manchester VT, Ascend Collection Hotel

10/10 Excellent

"There is free coffee. Room is clean. Elevator is a bit old. However the stuffs were extremely friendly and helpful."

Qiang 1-night trip

Posted 14 hours ago

Sun Lodge near Manchester VT, Ascend Collection Hotel

Toll Road Inn

10/10 Excellent

"Great location. Rooms were clean, well maintained."

Marianne 3-night trip

Posted 20 hours ago

Toll Road Inn

Bromley View Inn

10/10 Excellent

"This place was great! Bed was super comfy. Excellent view of the surrounding mountains. Definitely a solid place to stay!!"

Josh 1-night trip

Posted 2 days ago

Bromley View Inn

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 3 days ago

The Manchester View

Brittany Motel

8/10 Good

"Everything was totally fine except there was like one outlet in the entire room and the mini fridge was inexplicably loud when it would turn on and back off. It woke me up several times and I thought something serious was happening, but then it was just the fridge :/"

Courtney 1-night trip

Posted 3 days ago

Brittany Motel

The Inn at Manchester

10/10 Excellent

"Amazing place in a beautiful setting!"

Dawn 1-night trip

Posted 3 days ago

The Inn at Manchester

Four Winds Country Motel

10/10 Excellent

"The staff was very friendly and helpful."

John C 3-night trip

Posted 3 days ago

Four Winds Country Motel

Find out more about Dorset

Dorset Holiday Homes information

Number of reviews	152
Accommodation	629 Holiday Homes
Lowest Price	£199
Highest Price	£1,654

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Dorset on Expedia.com

Search Holiday Homes in Dorset

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Dorset holiday homes

1. 1812 House, 2 Stays, 1 home

2. Cozy 3 Bedroom Condo in the Heart of Manchester VT

3. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

4. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

5. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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

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

8. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

9. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

10. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

11. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

12. Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

13. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

14. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

15. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

16. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

17. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

18. New Ludlow Village Home with Stunning Okemo Mountain View

19. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

20. Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Find holiday rentals that suit your style

Top Dorset Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Find out more about Dorset

Dorset Holiday Homes information

Explore a world of travel with Expedia