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Compare 374 Vacation Homes in Millerton with updated reviews, rates, and availability.

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (23)
"We stayed at the house with extended family for a ski trip weekend at Catamount. The drive was 30mins away and the house a wonderful place to relax together after a long day on the mountain. The house is spacious, bright, clean and tastefully decorated. The layout is comfortable and practical. The lovely, open-kitchen was well-equipped and allowed us all to gather and chat pre and post dinner. The sauna is a great perk with gorgeous views! Highly recommend! Would love to come back in the summer...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (36)
"This was our second group visit to the Berkshire Farm House, and we plan to go back again! That fact says it all. "
Beautiful Berkshire Farm House on 160+ Acres

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (22)
"We made happy memories over a cold January weekend. We cooked together, sat around the fire, played games and dozed in comfortable beds with high quality linens. We enjoyed the view of the water and the twinkling lights on the property at night. The steam shower was divine. If you like cooking, bring good knives, a veggie peeler and good pans. Plenty of glassware and dishes and some cookware provided. "
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.4 out of 10, Exceptional, (20)
"Well located and comfortable "
The price is SAR 634
SAR 1,291 total
includes taxes & fees
31 Jan - 1 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

The Goshen Glass Chalet

9.4 out of 10, Exceptional, (29)
"Nice and cozy property. The host has been very responsive. "
The Goshen Glass Chalet

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
Spacious New Luxurious holiday house in lovely Hudson Valley

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...
Hudson Valley and The Berkshires getaway

Special Second Day November discounts @ the River. Text host for discount

9.8 out of 10, Exceptional, (12)
"Beautiful views of the river and was close to all. Place was a bit dusty and the larger bedroom had a very hard bed. Owner was kind and communicative."
Special Second Day November discounts @ the River. Text host for discount

Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

2.0 star property
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

The Farm at Hyde Park

9.8 out of 10, Exceptional, (65)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (13)
"Great property overlooking Hudson River. Close to Woodstock and Rheinbeck. Very good local restaurants for brunch and dinner. Host was great and responded quickly with all questions "
Hamptons on the Hudson in South Saugerties

Stockbridge Home, Come Experience The Berkshires!

10.0 out of 10, Exceptional, (24)
"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "
Stockbridge Home, Come Experience The Berkshires!

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (15)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9

Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

9.8 out of 10, Exceptional, (9)
"We loved our stay! Andrea responded to questions very quickly. The house was very clean and had everything we needed. We appreciated the treat that was left on the island. We were there only 2 nights and wish we stayed longer. We would definitely stay again. "
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (94)
"This was our fourth stay at this magnificent property and we continue to be amazed by its beauty and grandeur. Our host have provided us with everything to make our experience perfect. The house is well equipped and well-maintained. I would highly recommend this rental for a first-class experience. Thank you to George and Caitlin for their hospitality and kindness.."
A Grand property in Historic Stockbridge

LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK

10.0 out of 10, Exceptional, (39)
"house is clean, well maintained, and well stocked. Owners very responsive."
LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK

Large Barn styled vacation home that fits groups with space to spare.

9.8 out of 10, Exceptional, (57)
"Everything was ideal for our Thanksgiving get together. Setting and views were perfect, made even more so with a timely blanket of fresh snow. An amazing amount of cooking provisions allowed us to cook as if we were in our own kitchen. Lots of options for keeping a large group entertained, and sleeping accomodations that pleased everyone. Host was very helpful with check-in communications and gracious with check in and out times without other bookings adjacent to ours. All in all a very special...
Large Barn styled vacation home that fits groups with space to spare.
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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Other property types in Millerton

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (92)
"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "
The price is SAR 487
SAR 526 total
includes taxes & fees
6 Feb - 7 Feb
Micosta Leisure Inn

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (24)
"My daughter needed a place to stay while visiting for the holiday. Kevin was easy to reach and responded quickly. The apartment is very cute and was the perfect size. Everything was clean and had some nice personal touches. Im sure a summertime stay would be lovely, when the garden is in bloom"
The price is SAR 371
SAR 597 total
includes taxes & fees
26 Jan - 27 Jan
Mid-Century DJ’s Dream

The Farm at Hyde Park

9.8 out of 10, Exceptional, (65)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
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.