A calm lake reflecting a forest with autumn foliage.

Holiday Homes in East Dorset

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for East Dorset holiday homes

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

1. 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, (42 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is NZ$1,149
includes taxes & fees
25 Oct - 26 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

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, (1 review)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
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.

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)
"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). "
United States
Marissa H.
The price is NZ$1,295
includes taxes & fees
22 Oct - 23 Oct
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

4. 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 NZ$455
includes taxes & fees
13 Oct - 14 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A spacious kitchen with a central island, stainless steel appliances, and pendant lighting.

5. 1812 House, 2 Stays, 1 home

1812 House, 2 Stays, 1 home
Manchester
The price is NZ$1,419
includes taxes & fees
9 Nov - 10 Nov
1812 House, 2 Stays, 1 home
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

6. 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)
"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."
United States
Greg W.
The price is NZ$1,010
includes taxes & fees
8 Nov - 9 Nov
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

7. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful house! It had everything we needed for a fun and relaxing week. "
United States
Joshua
The price is NZ$749
includes taxes & fees
24 Oct - 25 Oct
Killington Retreat | Deck-Fire Pit-Mountain Views!
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

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)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is NZ$1,520
includes taxes & fees
28 Oct - 29 Oct
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A modern two-story house with a front porch, a staircase, and a driveway.

9. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is NZ$1,637
includes taxes & fees
21 Oct - 22 Oct
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A kitchen with wooden ceiling, a stove, a microwave, and a refrigerator.

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

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is NZ$796
includes taxes & fees
13 Oct - 14 Oct
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A large estate with a swimming pool, tennis court, and a spacious lawn.

11. The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!

The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great proximity to Bromley and Stratton, with easy access to plenty of restaurants in Manchester."
United States
Jessica G.
The price is NZ$3,613
includes taxes & fees
22 Oct - 23 Oct
The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

12. 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 NZ$622
includes taxes & fees
12 Oct - 13 Oct
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A cozy living room with a fireplace, comfortable seating, and a television.

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 NZ$748
includes taxes & fees
25 Oct - 26 Oct
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

14. 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)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is NZ$912
includes taxes & fees
1 Nov - 2 Nov
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Exterior

15. 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)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is NZ$1,221
includes taxes & fees
10 Nov - 11 Nov
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A two-story house with a covered porch and a garage.

16. 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)
"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. "
United States
Chi L.
The price is NZ$1,517
includes taxes & fees
12 Oct - 13 Oct
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

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)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is NZ$1,039
includes taxes & fees
1 Nov - 2 Nov
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.
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

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, (21 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is NZ$1,059
includes taxes & fees
12 Oct - 13 Oct
New Ludlow Village Home with Stunning Okemo Mountain View
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

19. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
Modern Mount Snow Gnarvana - Steps to Carinthia
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

20. 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)
"Great spot for a large group. "
United States
Brian G.
The price is NZ$1,874
includes taxes & fees
28 Oct - 29 Oct
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
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 East Dorset Hotel Reviews

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

10/10 Excellent
"Very unique house with lovely furnishings. Owners were very helpful and breakfast was delicious."
Garry 1-night trip
Posted 1 hour ago
Bentley House Bed and Breakfast

Find out more about East Dorset

East Dorset Holiday Homes information

Number of reviews
228
Accommodation
710 Holiday Homes
Lowest Price
NZ$455
Highest Price
NZ$3,613