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

Search Vacation Homes in Millerton

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Millerton vacation homes

Coffee/tea maker, fridge, microwave, oven

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, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is AED 3,269
AED 5,410 total
includes taxes & fees
29 Jul - 30 Jul
A Country Lodge Straight Out of the Pages of a Great Novel
TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (2 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 AED 1,172
AED 3,124 total
includes taxes & fees
9 Aug - 10 Aug
NEW: Chic Modern Barn Style Home in Fun Area
Dining

The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (8 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 AED 2,645
AED 3,964 total
includes taxes & fees
29 Jul - 30 Jul
The George is an elegant restored home in the Hudson Valley
TV, fireplace, printers

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, (7 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 2,321
AED 5,190 total
includes taxes & fees
24 Aug - 25 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

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, (6 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 AED 1,469
AED 3,087 total
includes taxes & fees
9 Aug - 10 Aug
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is AED 992
AED 1,493 total
includes taxes & fees
29 Jul - 30 Jul
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 876
AED 1,331 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Riverside Berkshires Retreat
Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AED 1,157
AED 2,110 total
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
Living area

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook
10.0 out of 10, Exceptional, (25 reviews)
"It was pet friendly, even for a dog, was comfortable for the entire family and is a great location with easy access to surrounding villages."
United States
Susan T.
The price is AED 1,010
AED 1,758 total
includes taxes & fees
23 Aug - 24 Aug
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (50 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is AED 4,505
AED 7,302 total
includes taxes & fees
2 Aug - 3 Aug
Great Barrington, Cabin Sleeps 14, Walk To Town
TV, fireplace, DVD player, books

Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is AED 694
AED 2,756 total
includes taxes & fees
9 Aug - 10 Aug
Mtn-View Retreat in Huson Valley: Great for Groups
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (8 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 AED 826
AED 1,395 total
includes taxes & fees
2 Aug - 3 Aug
Sweet Cozy Victorian in Housatonic. Close to everything.
Pool

Charming Hudson Valley Escape | Heated Pool & Fire Pit

Charming Hudson Valley Escape | Heated Pool & Fire Pit
Claverack-Red Mills
10.0 out of 10, Exceptional, (1 review)
"amazing property - best rental i’ve ever stayed at. can’t recommend it enough"
United States
jessica c.
The price is AED 1,976
AED 3,518 total
includes taxes & fees
12 Aug - 13 Aug
Charming Hudson Valley Escape | Heated Pool & Fire Pit
2 bedrooms, WiFi (free), bed sheets

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is AED 397
AED 745 total
includes taxes & fees
5 Aug - 6 Aug
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Exterior detail

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
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 753
AED 1,664 total
includes taxes & fees
30 Jul - 31 Jul
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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 AED 1,304
AED 2,461 total
includes taxes & fees
26 Aug - 27 Aug
Treetop Hideaway in Tyringham
Desk, WiFi

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is AED 684
AED 2,038 total
includes taxes & fees
2 Aug - 3 Aug
Charles Cottage Near Warren St New Renovation
Dining

Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck
Hyde Park
Luxe Mountain Getaway on Private Rd Near Rhinebeck
Private kitchen

Designer Home, Walk to Warren, Off-Street Parking, and 4-Bedroom/Loft

Designer Home, Walk to Warren, Off-Street Parking, and 4-Bedroom/Loft
Hudson
The price is AED 2,486
AED 4,627 total
includes taxes & fees
29 Jul - 30 Jul
Designer Home, Walk to Warren, Off-Street Parking, and 4-Bedroom/Loft
Outdoor dining

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is AED 951
AED 1,481 total
includes taxes & fees
29 Jul - 30 Jul
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Millerton Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"I love the Red Lion Inn because of its Old World charm. My husband thinks it could use some new rugs and fix cracked ceiling, but that does not bother me in the least. I just enjoy the place, including the dining room. Our room was very large and comfortable and very clean---no complaints at all. We have been there in the past and will be there again."
Sandra 3-night trip
Posted 3 hours ago
The Red Lion Inn

Explore a world of travel with Expedia