A rural landscape with a river, green fields, and red barns.

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Millerton vacation homes

A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

1. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is ￥29,464
￥102,116 total
includes taxes & fees
Nov 3 - Nov 4
Chic Barn Style * Fireplace * Near Stissing House
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

2. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥27,935
￥64,116 total
includes taxes & fees
Nov 2 - Nov 3
Cheerful 3-bedroom cottage with woodstove
A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is ￥70,902
￥101,598 total
includes taxes & fees
Nov 2 - Nov 3
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A wooden cabin interior with a bench, a rug, and a hanging plant.

4. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is ￥16,307
￥29,704 total
includes taxes & fees
Nov 8 - Nov 9
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with white cabinets, a large island, and a skylight.

5. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is ￥140,228
￥220,662 total
includes taxes & fees
Nov 3 - Nov 4
A Country Lodge Straight Out of the Pages of a Great Novel
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

6. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (13 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is ￥138,968
￥199,629 total
includes taxes & fees
Nov 2 - Nov 3
The George is an elegant restored home in the Hudson Valley
A wooden deck with a staircase leading to a covered porch area.

7. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is ￥16,733
￥20,859 total
includes taxes & fees
Nov 2 - Nov 3
All the comforts of home
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

8. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (7 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is ￥55,146
￥116,033 total
includes taxes & fees
Nov 5 - Nov 6
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

9. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥34,033
￥50,158 total
includes taxes & fees
Nov 9 - Nov 10
Home in Great Barrington
An outdoor patio with a stone table and chairs, a grill, and a stone fireplace.

10. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is ￥139,645
￥197,342 total
includes taxes & fees
Nov 13 - Nov 14
Maya's Garden House
521_Great Barrington_19

11. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Great Barrington
The price is ￥142,004
￥216,893 total
includes taxes & fees
Nov 3 - Nov 4
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

12. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥89,195
￥198,891 total
includes taxes & fees
Nov 4 - Nov 5
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A dining area with a wooden table, chairs, and a ceiling fan.

13. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥31,906
￥47,430 total
includes taxes & fees
Nov 2 - Nov 3
Leaf-Peeper Paradise in the Berkshires
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

14. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ￥31,512
￥52,271 total
includes taxes & fees
Nov 2 - Nov 3
Sweet Cozy Victorian in Housatonic. Close to everything.
A hot tub in a backyard with a house, trees, and a clear sky.

15. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is ￥141,095
￥225,281 total
includes taxes & fees
Nov 2 - Nov 3
Las Flores Villa
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

16. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥63,024
￥105,069 total
includes taxes & fees
Nov 16 - Nov 17
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden interior with a sectional sofa, a coffee table, and large windows offering a forest view.

17. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is ￥122,109
￥206,202 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful and Private Home Centrally Located in the Berkshires
A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

18. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is ￥31,512
￥67,122 total
includes taxes & fees
Nov 16 - Nov 17
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

19. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ￥42,226
￥84,603 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Hideaway in Tyringham
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

20. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is ￥53,744
￥96,816 total
includes taxes & fees
Nov 2 - Nov 3
Secluded Family Home in Serene Stockbridge Woods
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 Millerton Hotel Reviews

Interlaken Inn & Resort

Interlaken Inn & Resort

8/10 Good
"Sunnyside area could use some updating.The carpet seemed to be worn and drapes looked old."
Claudia 2-night trip
Posted less than an hour ago
Interlaken Inn & Resort

Find out more about Millerton

Millerton Vacation Homes information

Number of reviews
216
Accommodation
383 Vacation Homes
Lowest Price
￥20,859
Highest Price
￥225,281