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

Holiday Homes in Millerton

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Millerton holiday homes

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €390
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

2. 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 €704
includes taxes & fees
16 Nov - 17 Nov
Chic Barn Style * Fireplace * Near Stissing House
A wooden cabin interior with a bench, a rug, and a hanging plant.

3. 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 €181
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is €627
includes taxes & fees
25 Oct - 26 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is €1,296
includes taxes & fees
28 Oct - 29 Oct
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.

6. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is €321
includes taxes & fees
26 Oct - 27 Oct
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.

7. 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 €748
includes taxes & fees
3 Nov - 4 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A bedroom with a large bed, a chair, a desk, and a fireplace.

8. 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, (12 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 €995
includes taxes & fees
25 Oct - 26 Oct
The George is an elegant restored home in the Hudson Valley
A wooden deck with a staircase leading to a covered porch area.

9. 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 €130
includes taxes & fees
1 Nov - 2 Nov
All the comforts of home
A staircase with a wooden handrail and a white wall with a light switch.

10. 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 €253
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
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.

11. 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, (9 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 €1,177
includes taxes & fees
28 Oct - 29 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A dining area with a wooden table, black chairs, and a vase with green plants.

12. 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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is €309
includes taxes & fees
25 Oct - 26 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is €615
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A kitchen with white cabinets, a wooden countertop, and a woven basket.

14. 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 €405
includes taxes & fees
27 Oct - 28 Oct
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

15. 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 €615
includes taxes & fees
17 Nov - 18 Nov
Secluded Family Home in Serene Stockbridge Woods
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

16. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is €504
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
A hot tub in a backyard with a house, trees, and a clear sky.

17. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,121
includes taxes & fees
4 Nov - 5 Nov
Las Flores Villa
A modern kitchen with a central island, built-in oven, and a brick accent wall.

18. Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren

Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (1 review)
"A gem! Beautifully furnished, comfortable, well-equipped, and a short walk to town - we would return in a heartbeat."
United States
Katherine B.
The price is €854
includes taxes & fees
3 Nov - 4 Nov
Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren
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 Red Lion Inn

The Red Lion Inn

8/10 Good
"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"
carole 1-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Millerton

Millerton Holiday Homes information

Number of reviews
201
Accommodation
383 Holiday Homes
Lowest Price
€130
Highest Price
€3,121