Columbia County Holiday Rentals

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Top Holiday Rentals Destinations in Columbia County

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (94)
"Lovely caring owner. Beautiful room Hope to stay there again!"
The price is AU$221
includes taxes & fees
19 Mar - 20 Mar
Micosta Leisure Inn

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.6 out of 10, Exceptional, (5)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
Remodeled Lakefront retreat!! Come join us for Ski Season!!

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

9.4 out of 10, Exceptional, (23)
"The host was great with communication! The is such a cute little place but the layout is very nice and everything was updated and very nice! Would book again!! "
The price is AU$598
includes taxes & fees
21 Feb - 22 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, LIBRARY, BARN, TRAILS ON 60 ACRES!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, LIBRARY, BARN, TRAILS ON 60 ACRES!

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

10.0 out of 10, Exceptional, (24)
"Beautiful, remote property perfect for large groups! We'll definitely try get back there in the summer!"
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is AU$518
includes taxes & fees
24 Feb - 25 Feb
Near Tanglewood: Historic Summer Retreat

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

10.0 out of 10, Exceptional, (138)
"We were a group of 9 girls visiting in the winter for a secluded getaway. We wanted to rest and relax after the holidays. The house was very large and accommodated our entire party comfortably. Notably, the house is not your typical bare bones vacation property. For example, the beds were comfortable and had real pillows. It is clearly used by the owners and well-loved. We hired chefs for all of our meals and the kitchen had everything we needed. I would definitely recommend this property for...
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

Downtown Hudson Apartment: Walk to Cafes & River!

10.0 out of 10, Exceptional, (2)
"Great little place! Well equipped with everything we needed. Would stay at again…easy for visiting family nearby."
Downtown Hudson Apartment: Walk to Cafes & River!

Sanctuary of the Sacred Dream-Entire Property. Close to CATAMOUNT

Sanctuary of the Sacred Dream-Entire Property. Close to CATAMOUNT

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.

Waterfalls and Trails at 'The Mills At Green Hole'

10.0 out of 10, Exceptional, (10)
"Corporate retreat for annual planning"
Waterfalls and Trails at 'The Mills At Green Hole'

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

Loblolly Cottage - Enchanting Retreat set among towering pines.

10.0 out of 10, Exceptional, (37)
"Was a wonderful little cottage , we both enjoyed our stay and had a gracious host"
Loblolly Cottage - Enchanting Retreat set among towering pines.

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

9.6 out of 10, Exceptional, (24)
"Met our son and his girls for a little getaway. Very cool house complete with lots to do! Thank you. Hope to get to experience it during the summer months sometime."
The price is AU$1,582
includes taxes & fees
12 Mar - 13 Mar
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (118)
"Great for our two families. Fit 8 very comfortably. Close to Catamount where we went skiing and easy to get to town. Open concept house made it fun for family dinners and nighttime activities. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (75)
"We stayed there for our 45th anniversary trip and had never been to Hudson. This place was absolutely perfect. It was easy to walk everywhere so location was amazing. The apartment itself was bright and clean. The kitchen very well supplied and plenty of towels. We’d highly recommend! "
Apartment In Historic 1785 Thomas Jenkins House

All the comforts of home

8.8 out of 10, Excellent, (20)
"A nice no frills comfortable place. Tucked away from town but close enough to everything."
The price is AU$235
includes taxes & fees
21 Feb - 22 Feb
All the comforts of home

All comforts of home

9.8 out of 10, Exceptional, (37)
"Absolutely beautiful, cozy, and quiet. Highly recommend and look forward to staying again in the future. "
The price is AU$220
includes taxes & fees
23 Feb - 24 Feb
All comforts of home

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

10.0 out of 10, Exceptional, (11)
"We had our family Thanksgiving at this home and it was a great time. Enough space to cook a Thanksgiving meal, have a baking contest, play board games, and relax. The bedrooms were comfortable and everyone commented on how well they slept. More than enough bathrooms and showers with hot water for six people. Close to Great Barrington and Stockbridge for some small town vibes. Overall a great stay!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home

9.2 out of 10, Wonderful, (10)
"Simply loved the property! Enjoyed relaxing on the porch and sitting by the waterfall. Location was central to other sites we wanted to visit, too! We lost power overnight in the storm but made it work. Owner kept in contact with us and even started working on alternatives for us! Ran to get batteries for the lantern the house had and ice for the cooler to save our food! A few more candles and flashlights would have been great, but otherwise, a gem! Thku for your hospitality!"
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
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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