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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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.
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 AED 651
AED 1,503 total
includes taxes & fees
10 Nov - 11 Nov
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 AED 1,653
AED 2,397 total
includes taxes & fees
18 Nov - 19 Nov
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 AED 380
AED 692 total
includes taxes & fees
15 Nov - 16 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.

5. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
rural, serene + sophisticated space
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, (14 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 George is an elegant restored home in the Hudson Valley
A modern kitchen with white cabinets, a large island, and a skylight.

7. 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 AED 3,269
AED 5,144 total
includes taxes & fees
6 Nov - 7 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AED 793
AED 1,186 total
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

9. 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, (8 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.
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A wooden deck with a staircase leading to a covered porch area.

10. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AED 390
AED 486 total
includes taxes & fees
8 Nov - 9 Nov
All the comforts of home
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

11. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A dining area with a wooden table, chairs, and a ceiling fan.

12. 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 AED 744
AED 1,106 total
includes taxes & fees
8 Nov - 9 Nov
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.

13. 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 AED 617
AED 1,083 total
includes taxes & fees
8 Nov - 9 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
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.

14. 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 AED 2,089
AED 4,648 total
includes taxes & fees
8 Nov - 9 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

15. 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 AED 1,469
AED 2,449 total
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A rustic interior with a brick oven, wooden beams, a sofa, and a dining area.

16. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is AED 2,901
AED 4,204 total
includes taxes & fees
6 Nov - 7 Nov
Maya's Garden House
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.

17. 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 AED 735
AED 1,565 total
includes taxes & fees
18 Nov - 19 Nov
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A hot tub in a backyard with a house, trees, and a clear sky.

18. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AED 3,289
AED 5,252 total
includes taxes & fees
6 Nov - 7 Nov
Las Flores Villa
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

19. 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 AED 1,253
AED 2,257 total
includes taxes & fees
9 Nov - 10 Nov
Secluded Family Home in Serene Stockbridge Woods
A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

20. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is AED 2,847
AED 4,670 total
includes taxes & fees
11 Nov - 12 Nov
Beautiful and Private Home Centrally Located in the Berkshires
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

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Me and my daughter has such an amazing stay at the Litchfield inn. It was absolutely beautiful clean,cozy, smelled so good and the staff was very help and friendly . Hope at the front desk was amazing!! We came for my daughter’s birthday and would definitely come back on our next visit. The complimentary breakfast was exceptional as well. Perfect area nearby to New Milford which has Gilmore girls/inspo at the town green. Found the gazebo it was absolutely perfect girls trip for us we loved it here. 10/10 !!!!!!"
Stephanie 2-night trip
Posted 17 hours ago
The Litchfield Inn

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