Tiny house holiday rentals in Columbia County

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Popular amenities for Columbia County tiny house rentals

Family-friendly tiny house rentals

Apartment in Great Barrington
4.81 out of 5 average rating, 274 reviews

Beautfiul, modern, GB apartment

DerekRating, 5 stars3 weeks ago
Wonderful guest suite in a cool town with great access to nature. Molly was very helpful and kind, would definitely stay again!
Guest favourite
Guesthouse in Germantown
4.97 out of 5 average rating, 74 reviews

The Guest House

StephenRating, 5 stars7 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!
Guest favourite
Private room in Hillsdale
4.81 out of 5 average rating, 73 reviews

Sweet Butter and Cream Guestroom

StephanieRating, 5 stars2 weeks ago
We had a really great time at Merrys house! She was very communicative and gave us a lot of nice recommendations for the area. Our puppy had a really good time too with Merry's 3 dogs and was able to run free and enjoy the large outdoor space on the property. We can't wait to go back soon.
Guest favourite
Tiny home in Germantown
4.89 out of 5 average rating, 106 reviews

Artist A-Frame at Gatherwild Ranch

MeganRating, 5 stars7 months ago
Beautiful little a frame! Peaceful property with lots of little things to do to tucked around - would love to come back and use the pizza open on the summer! The communal bathroom and kitchen area was beautifully designed and a short walk from our cabin. Appreciate the extra touches (firewood, ability to use sauna, s’more kits) note that these are for an extra cost. Thank you!!

Tiny house rentals with a patio

Top Guest favourite
Tiny home in Germantown
5 out of 5 average rating, 32 reviews

Best mountain views anywhere

RobertRating, 5 stars2 weeks ago
Adam was a great host. He met us at the tiny cabin and explained the details of the cabin and what to do around the area. Adams place is very peaceful and off the grid. His property is walkable and the pathway is a loop around beautiful nature on the property. There is a lot to do in the area and the close to the surrounding towns that you can get to within a 10 to 20 minute drive. We'll be back again.
Top Guest favourite
Cottage in Livingston
4.99 out of 5 average rating, 85 reviews

Waterlily Lakehouse - Modern+Waterfront+Retreat

LyndsayRating, 5 stars1 week ago
My friends and I loved our weekend getaway at Vivian's lake house. Vivian was a very responsive host and provided clear instructions that made our stay seamless. The space was super clean, modern, and easily accommodated all 8 of us. The highlight of our trip was spending time on the lake with the provided kayaks and paddle boards. We enjoyed ending the day by grilling and sitting around the fire pit. We wish we had stayed longer!
Superhost
Tiny home in Hudson
5 out of 5 average rating, 10 reviews

Unique Tiny House Glamping

KarinaRating, 5 stars2 weeks ago
Jordan and I were very aligned in our approach to health and wellness, which made this stay especially enjoyable. I appreciated that he used fragrance-free laundry detergent and stocked the space with clean, environmentally conscious cleaning products. He was also highly responsive and even directed us to a beautiful natural spring nearby where we could source fresh water. A thoughtful and gracious host—I'm only sorry I didn’t have more time to stay and get to know him and his family better!
Guest favourite
Tiny home in Catskill
4.93 out of 5 average rating, 243 reviews

Venster- 2 hours to NYC,Hudson Amtrak, Kaaterskill

RicardoRating, 5 stars1 day ago
Great little getaway. Nice fire stove outside to sit by with a beautiful forest. Floor to ceiling window in the cabin to admire the nature. Would recommend!
Top Guest favourite
Tiny home in Chatham
4.99 out of 5 average rating, 277 reviews

Boutique TINY home+private hot tub-walk to Main St

LadipoRating, 5 starstoday
Our stay was truly wonderful and a blessing! We went away for our anniversary. Everything matched or surpassed expectations! Heidi is so proactive and responsive -- a 5 star host! It couldnt have been any better. Looking forward to returning! Such a lovely space and town. Thanks Heidi!
Top Guest favourite
Cabin in Hudson
4.96 out of 5 average rating, 79 reviews

Cozy Grove Luxury Cabin

KarinaRating, 5 stars3 weeks ago
Stellar stay at Jessica’s home — top notch amenities that made us feel right at home but better! Very much appreciated the coffee bar, amazing couch & TV setup, and very comfortable bedding. We took advantage of the recommendations of the area that were thoughtfully put together. Highly recommend and great for luxurious getaway!
Guest favourite
Home in Egremont
4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars3 weeks ago
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!
Guest favourite
Tiny home in Ghent
4.96 out of 5 average rating, 53 reviews

Country Getaway Tiny House in woods w/pool/Sauna

JackieRating, 5 stars7 months ago
Our stay was fantastic! The property exceeded our expectations from the moment we arrived. Every detail was thoughtfully arranged, making us feel welcome and comfortable throughout. The space was spotless had everything we needed for a perfect getaway. What truly made our experience outstanding was Dennis’ kindness—they went above and beyond to accommodate us, even letting us stay an extra night!!! You can feel that this place was created with love and peace; it’s a serene escape that radiates positive energy. The private walking trails were beautiful and gave us a peaceful space to explore nature, and at night, we experienced the most beautiful night sky we have ever seen—absolutely breathtaking! Communication was quick and helpful, and the check-in process was seamless. This is a hidden gem for anyone looking for a blend of comfort, charm, and natural beauty. I can’t wait to bring my family with me next time to experience this incredible place together.

Tiny house rentals with outdoor seating

Cabin in Ghent
4.85 out of 5 average rating, 41 reviews

Charming-Rustic cabin in the woods.

MaryRating, 5 stars12 months ago
This is our second time staying here, we loved it so much the first time. We definitely recommend staying here for a quiet, peaceful, beautiful getaway!
Guest favourite
Cabin in Catskill
4.97 out of 5 average rating, 30 reviews

Romantic Getaway

TylerRating, 5 stars2 months ago
We enjoyed our stay! The cabin was private and so cute. It was just as described. When we arrived, we called Silivia to confirm where we could go walking— she answered peomptly and was very helpful. Would recommend. Would come again. Thank you!!
Guest favourite
Island in Pine Plains
4.96 out of 5 average rating, 83 reviews

Magical Private Island Retreat in Pine Plains

LindsayRating, 5 stars3 weeks ago
Rony Island is as cute as it looked online. Perfect lil getaway for us for the weekend. Hosts were so responsive and had lots of recommendations — we had a beautiful dinner at Stissing House and my partner Jon went up to the fire tower for a hike. We spent our last hour at the island slowly paddling the canoe around the whole lake. Thank you for a lovely stay!
Guest favourite
Cottage in Valatie
4.89 out of 5 average rating, 66 reviews

Hudson Lake Resort: MV Buren Cottage III

LeidyRating, 5 stars3 weeks ago
Beautiful property right on the lake. The cabin was very clean and equipped with everything we needed for a relaxing getaway. Lots to do in the area, hiking, food, bars. We will be back :)
Private room in Catskill
5 out of 5 average rating, 3 reviews

Hudson Valley Resort Tiny House+pool & fire

VijayRating, 5 stars20 months ago
We had a fantastic weekend at Treetopia Tiny Home Camping! The tiny home was cozy, clean and perfect for our family of four. The setting amidst nature was serene, and the kids loved the unique experience. The amenities were great, and the staff was friendly and accommodating. We enjoyed hiking trails, campfire in the evenings, and stargazing at night. A memorable family getaway!
Tiny home in Canaan
4.9 out of 5 average rating, 68 reviews

The Heronbrook Hideaway

AndrewRating, 5 stars12 months ago
Wonderful isolated cabin. Do be prepared for camping life but the Stewart's gas stations provide easy access to ice and other supplies. There were a few things that needed fixing but the host was very responsive. Beautiful A frame. No houses in sight. Excellent view of the mountain and terrific bird life in the field.
Private room in Hannacroix
5 out of 5 average rating, 5 reviews

My Little Cabin

PaoloRating, 5 stars57 months ago
It was a pleasure to stay at the cabin! Deborah was such a great host! Walked in after a 3 hour drive to treats and fruits. She was very helpful explaining and showing were everything is! Location was close enough to town and far enough to be peaceful and quiet! Loved this cabin!!
Guest favourite
Cottage in Hudson
4.96 out of 5 average rating, 26 reviews

Saltwater Pool & Cottage Loft with Sauna in Hudson

RajatRating, 5 stars1 month ago
We stayed at Todd’s place for 2 days in May. I thought the bomb and the setting is very beautiful and the house adequate. We enjoyed with all their pets and had a great time. Would recommend for couples. The pool is great as well, though just check for the pool hearing beforehand, since it takes quite a bit of time to heat up. But all in all had a great time

Destinations to explore