Guesthouse vacation rentals in Columbia County

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Popular amenities for Columbia County guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Tivoli
4.94 out of 5 average rating, 248 reviews

Light-filled guest cottage

ElyseRating, 5 stars2 weeks ago
Gorgeous place in a beautiful town. About a thirty minute walk (or 4 minute drive!) right into downtown with cute shops and restaurants. The cottage is beautiful, clean and so cozy. Highly recommend.
Guest favorite
Guesthouse in Germantown
4.97 out of 5 average rating, 74 reviews

The Guest House

StephenRating, 5 stars6 months ago
Stayed in the guest house for the night, and was a peaceful and pleasant stay! Hosts were very friendly and amenable — watching the goats was a nice bonus as well!
Top guest favorite
Guesthouse in Pine Plains
4.97 out of 5 average rating, 79 reviews

Cozy Cottage by the Pond

CameronRating, 5 stars6 months ago
Deborah was a great host and followed up to any questions or concerns. The cottage was quaint but had just the right amount of amenities. The space was welcoming and the surrounding yard/pond are quite beautiful. Especially during the fall color change. There’s the occasional deer or owl in the yard you can often see over morning coffee.
Guest favorite
Guesthouse in Hudson
4.99 out of 5 average rating, 83 reviews

Cozy cottage on Angus Farm, 15 mins from Hudson.

LauraRating, 5 stars2 weeks ago
Definition of idyllic! We had such a wonderful stay at Kim's house. My husband, 3yo, and 8mo spent a few days "on the farm" (as my 3yo lovingly called it) and could not have felt more relaxed. The charming cottage is an easy 15-minute drive to downtown Hudson. We enjoyed rocking on the front porch with our coffee, watching the goats lazily graze along the edge of the pond beautifylly lined with trees. Truly relaxing and felt like we were living in a postcard. Kim was very friendly and responsive and had great local suggestions. Would happily revisit Angus Farm next time we're in Hudson!
Guesthouse in Germantown
4.71 out of 5 average rating, 48 reviews

Quaint Rural Cottage Immersed in Nature

PeterRating, 5 stars14 months ago
Marianne is a kind and generous host. Not sure if she can do it every time, but we had croissants, butter, jam, fresh fruit, and chocolates waiting for us. She also treated us to enough fire wood for our first fire. Rustic, spacious cottage located within 15-20 minutes of Hudson and Tivoli. Visited Olana and Poet's Walk Park. Some great restaurants. My girlfriend said she wanted to go back and stay for 2 weeks (we will see). Overall, I was glad to find this property for a last minute getaway.
Top guest favorite
Guesthouse in Germantown
4.98 out of 5 average rating, 61 reviews

The White Barn: A Bright Barn Loft in the Country

CarolinaRating, 5 stars6 months ago
My husband and 2 year old stayed at Ellen’s barn for the weekend. The space was very big, clean and the bed was very comfortable. The location is excellent for exploring the area, we didn’t spend much time in the barn as we spent much of our day exploring. Would highly recommend Ellen’s place!
Guest favorite
Guesthouse in Canaan
4.93 out of 5 average rating, 183 reviews

Airy cottage with meadow views in The Berkshires

AlexRating, 5 stars5 months ago
I really enjoyed my stay at Galina's cabin and would definitely stay again. The cabin itself is well laid out and decorated, and was very clean when I arrived. The location was perfect for what I wanted.

Guest house rentals with a patio

Top guest favorite
Guesthouse in Hudson
5 out of 5 average rating, 45 reviews

Hudson Countryside Guest Cottage w/Amazing Views

DaiweiRating, 5 stars4 days ago
An unparalleled rustic living experience! The house is spotless and well-maintained, offering convenient amenities while surrounded by charming restaurants and fascinating attractions. If you prefer a tranquil lifestyle, this is absolutely a must-visit destination!
Top guest favorite
Guesthouse in Stuyvesant Falls
5 out of 5 average rating, 24 reviews

The Falls at Lindenwald Cottage

LizRating, 5 stars1 month ago
Perfect location and space for my husband and I for a quick weekend getaway! The falls is literally across the street and It was so nice to be able to walk over and see it. The airbnb felt very central as it was a 20-30 min drive to most places near Hudson/Catskills that we were trying to see. Would stay at again if it was just us two.
Top guest favorite
Guesthouse in Hudson
4.98 out of 5 average rating, 80 reviews

Stylish, New Carriage House on Warren St!

RobRating, 5 stars4 days ago
Our second stay at Marie's carriage house in Hudson was delightful. The house itself was impeccably clean and so comfortable – it felt like a home away from home. The location couldn't have been better. We were just a short walk away from all the charming shops and fantastic restaurants that Hudson has to offer. It made it incredibly easy to pop out for a bite to eat, grab a coffee, or browse the shops. We took advantage twice of the discount at Marie’s hip wine bar. Marie was again a wonderful host. Her communication was excellent from start to finish. She is prompt in her responses and provided all the information we needed for a smooth and enjoyable stay.
Superhost
Guesthouse in Valatie
4.89 out of 5 average rating, 74 reviews

Hudson Berkshire Lake Log Cabin

EmmaRating, 5 stars2 months ago
Great cabin! Francois and Ann were very responsive and friendly. The cabin was amazing and the area was beautiful! The perfect place to get away from the busyness of everyday life and recharge.
Guest favorite
Guesthouse in Catskill
4.8 out of 5 average rating, 5 reviews

Modern village studio with a forest view

AdelaRating, 5 stars4 days ago
We absolutely loved our stay here! The apartment is so beautifully and thoughtfully decorated (you can really tell Ry is a furniture designer). We loved the heated bathroom floors, huge bathtub, massive windows, easy-to-use fireplace, well-stocked kitchen, and the comfortable bed. Georgina and Ry were super kind and communicative hosts. Catskill is a great town (we much preferred it to Hudson). Highly recommend for 2 guests! We’d love to come back.
Superhost
Guesthouse in Great Barrington
New place to stay

Poolside Long Pond Bungalow!

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Hudson
4.99 out of 5 average rating, 83 reviews

Cozy cottage on Angus Farm, 15 mins from Hudson.

LauraRating, 5 stars2 weeks ago
Definition of idyllic! We had such a wonderful stay at Kim's house. My husband, 3yo, and 8mo spent a few days "on the farm" (as my 3yo lovingly called it) and could not have felt more relaxed. The charming cottage is an easy 15-minute drive to downtown Hudson. We enjoyed rocking on the front porch with our coffee, watching the goats lazily graze along the edge of the pond beautifylly lined with trees. Truly relaxing and felt like we were living in a postcard. Kim was very friendly and responsive and had great local suggestions. Would happily revisit Angus Farm next time we're in Hudson!
Guest favorite
Guesthouse in Chatham
4.92 out of 5 average rating, 25 reviews

Tranquil Guest House, Chatham NY

ElisabethRating, 5 stars2 months ago
We loved this house! The interior was spotless, well-considered, and tasteful. The beds were so comfortable and the kitchen was perfect. There is a picturesque stream at the rear of the property. Lucy was thoughtful and responsive: It snowed heavily one evening, and she immediately had the driveway plowed. We skied at Catamount, visited Mass MoCA, and had a delicious dinner at The Prairie Whale in Great Barrington. We can't wait to return!
Guest favorite
Guesthouse in Red Hook
4.94 out of 5 average rating, 93 reviews

Private Cottage, Walk to Restaurants and Shops

beccaRating, 5 stars3 months ago
Robin's place was warm and comforting with a great kitchen, an easy walk into town, and lovely outdoor areas. Robin was very accommodating, kind, and welcoming. We would be very happy to come back again!
Top guest favorite
Guesthouse in Hudson
5 out of 5 average rating, 27 reviews

Serene one bedroom guest house with fireplace.

AllisonRating, 5 stars6 months ago
One of the best Airbnbs we've stayed at. We loved the interior design and how cozy the space was. The location is beautiful and peaceful. Highly recommend.
Top guest favorite
Guesthouse in Great Barrington
4.96 out of 5 average rating, 118 reviews

Sweet Victorian in Housatonic

AnnieRating, 5 stars3 weeks ago
Me and my family have stayed at Emma’s twice now, and we’ve loved it both times we’ve stayed here. I love how bright and clean the space is, and so functional for us to stay in as a family. The kids especially love the bunk bed, and the grandparents loved the comfy beds, and I loved getting some work done on the beautiful desk on the second floor. We love this place and can’t wait to come back in the summer to sit and eat meals on the front porch. The neighborhood is great! It’s so convenient to be able to walk to the playground and bike path, Common Pub, and package store.
Guesthouse in Chatham
4.97 out of 5 average rating, 29 reviews

Restorative retreat- cozy Hudson Valley getaway

WeiRating, 5 stars18 months ago
We (me + two other adults) had an amazing stay at Justine and Scott's. The cottage is very charming and spacious with a full kitchen for cooking. The kitchen and living room area overlook a beautiful flower garden and pond. The dahlias in every room were a lovely touch. The beds were comfy and cozy. The location can't be beat - under 20 minutes to Hudson NY and ~30 minutes to a few Berkshires towns. I would gladly return!
Superhost
Guesthouse in Great Barrington
4.84 out of 5 average rating, 58 reviews

1-bed unit 3/4 mi. from GB dwntwn.

JosephRating, 5 stars5 days ago
This was our 2nd stay at Christian's place. Every was great once again. Peaceful, beautiful with lots of things to do in the area. Thanks Christian, we will be back again!
Top guest favorite
Guesthouse in Chatham
5 out of 5 average rating, 19 reviews

Idyllic and cozy guesthouse

CoryRating, 5 stars5 months ago
Such a perfect place to visit. The guest cottage is private up on the hill overlooking a pond, a massive porch, and all the views. I would go back to this location again. The host was kind and hospitable above and beyond. Bimis canteen for dinner was fantastic. Ty for a great visit.

Destinations to explore