
House holiday rentals in Columbia County
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Top-rated house rentals in Columbia County
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House rentals with a pool

Red House on the Hudson
We loved our stay! Comfortable beds. Super tidy and best of all the view! If only we were there in the summer, we would’ve used the pool. Would love to return!

Fabulous Heated Pool, Screen Porch, Ping Pong!
We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.

Columbia County Farmhouse with Pool
The house and land are special. Much thought and care have been given to make this place feel both quietly elegant and homey. Beauty inside the house and out, the rural setting, the comfortable beds, spacious rooms, unusual architecture - all contributed to our desire to return.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Beautiful house in upstate with a hot tub and barbecue that allowed us moments that we won’t forget. Chris was very responsive and maintained the communication throughout our stay. The house was spacious, clean, great amenities and extra care from the host. The location was also good, close to Hudson but private. We loved it and hope to be back soon!

Berkshire Mountain home views, pool, Queechy Lake
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

Modern Barn on 12 acres w Sauna, FirePit+swimming
Great place. As described. Met our expectations.

Farmhouse and Guesthouse w Pool, Pond and Sauna!
Donna was an amazing host and extremely responsive. The property was beautiful and exactly as described in the listing. The pool, pond, sauna’s made the entire experience feel like a special escape from the city. I highly recommend this property and can’t wait to go back!

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse
Arp’s place was perfect for a weekend escape in the Catskills. The place was beautiful and spacious for our group of 8. We really enjoyed all the amenities and how close it was to many sights. We would love to stay again!
Weekly house rentals

Modern, cozy log cabin in Copake
Our stay at Julia's home was perfect! We all felt right at home, our grand daughter had lots of books, which she loves and other kids toys. The log cabin was more beautiful than pictured and the claw foot tub in the upstairs suite was the icing on the cake.

Fenced yard, playroom & the Berkshires - $0 fees
We really enjoyed staying here for two nights with our dog. The yard was the perfect size for him to run around, and I truly appreciated how dog-friendly the property was. The peaceful and private setting, with the soothing sound of the nearby creek, made it a relaxing getaway. I was impressed that each room had its own controllable AC unit—super convenient! All the bathrooms were well-stocked with plenty of toilet paper, and the kitchen was incredibly well-equipped with everything we needed, all the utensils and appliances you need. Overall, a wonderful stay!

Hudson New York Grey Victorian
This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!

Fantastic Cottage/Insane Views/Trails/Fireplace!
What a dream! We loved Martina’s place - the view was incredible, and we felt right at home in the space. We would definitely stay here again.

Secluded Post-And-Beam Retreat
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

A sunny, quiet chalet beautifully decorated.
Beautiful, clean and great location! We were up skiing at Catamount so the location was ideal, and the sauna was a nice treat everyday. The house is beautifully decorated and spacious and open. There are a few different levels so plenty of room to spread around with a separate spacious TV/exercise/bunk room in one of the levels. The 2 king beds and twin beds in the bedrooms were all very comfortable and each of the bedroom had their own bathroom next door. The kitchen is fully stocked with kitchenware and necessities/spices etc. Kids went sledding and we even hiked up several times to the top of the hill with great views. Carolyn was very responsive and accommodating.

Rushing Rapids Cottage – a birdwatcher's paradise
We loved staying at Jeffrey and Juan’s quiet home on the rushing Chittenden Creek! Jeff is a communicative, friendly, and accommodating host and would absolutely recommend his place to others. I surprised myself at how much I loved the bird watching (don’t worry, Jeff has binoculars and a book to guide you!). Don’t miss out on the Empire trail for early evening walks! My husband and I stayed at their home for two weeks as we both work remotely and there was plenty of space to spread out and take calls. The plant room in their home is so beautiful that people complimented my ‘digital’ background on zoom! Would absolutely stay again.

320 State - Beautiful Backyard 2 blks from Warren
As others have said, this place was even better than the photos - beautiful, long 1 bedroom apartment, with a beautiful antique design, large windows, and cozy couches. Claudia was excellent to communicate with. Would absolutely stay here again!
Private house rentals

Germantown retreat on 25 acres
We were there for the NY Sheep and Wool Festival so we didn't spend much time in the house, but it was very comfortable while we were. The place is off a long driveway and felt very private. We really appreciated the nice touches of delicious chocolate chip cookies and a stocked tea cabinet. This place is perfectly charming.

Yellow Door House
We’ve stayed at Kathy’s Yellow Door many times, or kids call it our vacation home. Kathy is a great host and she will always strive to make your stay enjoyable and stress free (unless you have a toddler like we do). Don’t hesitate to stay at Yellow Door.

19th Century Mill House with River View
My family enjoyed staying at Django’s place immensely. It is a curious place, a home that feels like it has had a rich past. The art, books, & music all reflect a unique taste and we appreciated the claw foot baths, and the sublime views of the Stockport creek. All considered it was a beautiful spot in the Hudson Valley, & only ten minutes from downtown Hudson. What more can you ask for?

Modern and Stylish Country Lakeside Cottage
Hello - Great to be back in Maureen's home. Super excellent location 5mins or so to Great Barrington and close to everything the Berkshires has to offer. Home is really amazing for a romantic weekend away, my partner and I both loved everything about the home and the surrounding property. no notes.

Peaceful Berkshire Getaway (A/C, Lake Access)
Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!

Tranquil & Private River Home
Robins place was lovely. Totally spotless and well appointed. There was everything you needed for a great stay and then some. It’s beautifully situated right on the river but it is down a dirt road so be prepared for a short but possibly bumpy ride. We had a minor issue figuring out the thermostats but Robin got back to us immediately and we got it straightened out. She left plenty of firewood for us so we had a cozy fire going on thanksgiving. We hope to return when it’s warm do we can enjoy the property and the river. A great stay and a super host

Cozy Country Cottage
I’ve stayed at a few airbnbs in Hudson and this was my favorite place so far. Peaceful, comfortable, clean, and tastefully decorated. Comfortable beds, spacious rooms, two bathrooms, and washer/dryer made this stay feel like home. I can’t recommend enough, and plan to stay here again the next time I’m in town!

Cheerful Home with Stunning Views
This was a great location with wonderful views. The home was clean and well stocked and the photos do not do the views justice. We enjoyed the fire place and there was plenty of supplied wood. The grounds were great to explore for us and our dog. The team was very proactive cleaning the driveway of snow and ice. It was a very relaxing and enjoyable time.
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- Hunter Mountain
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Howe Caverns
- Saratoga Race Course
- Saratoga Spa State Park
- Albany Center Gallery
- Berkshire East Mountain Resort
- Taconic State Park
- John Boyd Thacher State Park
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Opus 40
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Kent Falls State Park
- Beartown State Forest
- Naumkeag
- Pineridge Cross Country Ski Area
- Otis Ridge
- Brignole Vineyards
- Things to do Columbia County
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