
Cottage holiday rentals in Shandaken
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Top-rated cottage rentals in Shandaken
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Popular amenities for cottage rentals in Shandaken
Cottage rentals with a hot tub

Hot Tub, Playground, 3 Acres, and Much More!
Highly recommended — especially for families with young children! The property has everything you could need, and there’s even a charming farm nearby (just be sure to check their hours in advance). The hosts were incredibly responsive and helpful throughout our stay. The house was spotless and had such a welcoming, positive energy. With so much land to explore, you truly don’t need to leave the property if you bring your own food and supplies. We had a wonderful experience and will definitely book again in the future!

Couples Getaway, Hot Tub, 3 acres, 5mi to Kingston
We had a lovely stay at kim’s. The location was great, having a hot tub was really nice even with the weather getting warmer, the space was very clean and kim was very responsive to us throughout the whole stay.

Driftwood Cottage on Welcome Lake-peaceful retreat
Couldn't have been happier with this cottage. Modern appliances, beautiful surroundings, quiet, gorgeous view overlooking the lake. The kitchen and master bathroom were standouts. Would stay here again. Bob and Julie did a fantastic job communicating before, during, and after the stay.

Renovated Country Cottage w/ Hot Tub & View
This was a nice AirBnB for the area, cozy and felt somewhat secluded despite being viewable from the main road. Perfect for a small dog to roam around on the grassy area, and the hot tub looking out into the back was a nice touch and enjoyable to sit in. We were looking for a relatively short get away from the city, quiet and close enough to things in the area to enjoy, and this fit the bill perfectly. The house was very clean with very clear instructions, and nice touches that made it feel cozy. Highly recommend for 2-4 people, particularly with small dogs.

Country Cottage w/ HOT TUB & Views
Everything about our stay was perfect! The house was spotless, cozy, and located in a great area. The host went above and beyond — always in touch, helpful, and kind. We truly felt welcomed and taken care of. Would absolutely stay here again!

Hot Tub & Chic Catskills Woodstock Design Retreat
We always stay at Little Willow when we go skiing at Belle Ayre. I think our three years and running relationship with the house tell you all you need to know about working with the Little and Littler gang and their spot.

Woodstock Carriage House HotTub FirePit Pool
Three friends met at this beautiful carriage house with the feel of a French chalet! We stayed two nights with varied weather conditions. The house, grounds and location was perfect. Hot tub was used and so relaxing. The surroundings were beautiful and peaceful. The host, Diane was very helpful and friendly. What host makes scones each morning and delivers them warm?! Visited the Ashokan Reservoir trail, Opus 40, and Woodstock. Recommend this home highly. You won’t be disappointed!

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK
Great place. Fun water activities for the kids. Our dogs allowed to come was excellent. A little light on cutlery in the kitchen, but we made it work. Would recommend and would stay here again!
Pet-friendly cottage rentals

Peace Cottage
I booked Nidhi's place for one night for myself and a guest to attend a show at Bearsville. The placement of everything, inside and outside, created an intentional sense of comfort. My guest arrived after me - without a thought, we ended up at the kitchen table talking for hours before the show. Again, the placement of this conversation spot felt intentional, but only after we found ourselves engaged in it. The outdoor surroundings are utilized to not only accent, but to enhance the indoor setting. The whole experience felt private and safe, and allowed us to share a really precious window of time for reconnection and decompression. In addition to the appealing aesthetics (the chosen blue for that kitchen!), the bedding was a treat to come back to at the end of the night - so inviting and equally comforting to find yourself wrapped up in in the morning. Nidhi so kindly messaged me out of concern for the very high winds we were experiencing (prepared with a generator), but no issue.

Cozy off grid cottage Big Pine trees in Catskill
This cabin is so very special—and has an artists touch! It is cozy (especially with the wood stove going), spacious for being a one-room size, and has everything you need to disconnect and recharge. We will absolutely be back and appreciated the clear and easy communication as well!

Woodstock Dog friendly Cottage in Town; large yard
the location was incredible! We enjoyed walking the 50 feet into town for cute shops and boutiques. Ann had a great list in the house of restaurant recommendations that we found very helpful. Pictures do not capture the charm and coziness of this home, it is a very special property. the backyard was gorgeous and large also and we could hear a waterfall in the distance. We loved our little mountain getaway and will definitely stay here when we return to Woodstock.

Hudson Valley Cottage
This was so charming & cozy, while also being conveniently close to nature nails & downtown Woodstock. We thoroughly enjoyed our stay & would recommend!

Kapitan’s Cottage: Private Retreat with Salt Pool
The cottage is lovely, clean, and immaculately decorated. Great taste. We enjoyed the pool, which was perfect for our four year old given how shallow half of it was, and how the temperature was perfect, even on days when it wasn’t too hot outside. We hadn’t realize that the kitchen didn’t include an oven or microwave—but even so, we had a great time and enjoyed the fire pit! WiFi was a bit spotty but the hosts went above and beyond to try to help. Highly recommend!

Bear Cottage in Phoenicia - Everything Walkable
A wonderful home with lots of personal touches. Great for writing retreat, a base for hiking or to be in town itself. Looking forward to staying again.

1930's Cottage charm cozy air cond. near hiking
If you’re an artist looking for an inspiring and quaint place filled with kitsch and charm this place is perfect!

🌟Riverfront Cottage W/2 Bedrooms Catskills 🌟
We had a great few days at Robert and Sandra's adorable place. Exploring the river and state lands bordering the property was awesome. Hope we can stay at the River House again.
Private cottage rentals

Cozy Mountaintop Cottage for a Catskills Escape
Cute house in the Catskills! Close drive to Tannersville, Hunter - for restaurants. Very close to trailhead for Devils Path and Kaaterskill. Clean, comfortable, and for just the two of us, plenty of space!

Catskills Cozy Retreat:Comfy Beds, Firepit, & More
Had a wonderful stay at Michael’s place. Quiet and centrally located to fishing spots we planned to go to. Would highly recommend and hopefully plan a return trip next year.

Cottage with Private Deck on 8 acres of Woods
The stay at Ashlie’s was just perfect. The cabin is so intimate and secluded, but very close to everything you might wanna check out! Ashlie was very friendly, I would definitely stay again!!

Old Mill Cottage - Upstate Mountain Views
I’m so glad we stayed there! We had a beautiful breakfast on the deck one day and looked at all the stars at night. Perfect place.

Little Cottage Under the Ridge
Jaclyn's airbnb is located in a wonderfully private area in the Catskills, close to New Paltz and many nice restaurants, amenities and hikes. The small home has been tastefully remodeled and outfitted with great appliances. A perfect getaway for a couple. We will be back!

Fabulous Lemon Cottage in Rhinebeck, NY
By far one of the best airbnbs I have ever stayed at! The cabin was beyond adorable, comfortable, clean, so well decorated and very private. It was so relaxing with great outdoor areas to hang out, places inside to read, comfortable den to watch movies and super comfortable bed. Would definitely come back!!

Little Yellow Cottage New Paltz - Kitchen wash/dry
I usually stay in village of New Paltz so was a little apprehensive staying a bit outside of village. But I actually now prefer the situation as it's not that far to all the action and the cottage is amazing, which more than makes up for the minor driving inconvenience. Highly recommend!!

Blue Mountain Cottage
Great cabin for a weekend getaway. The kitchen and living areas were spacious and the lofted bedroom was cozy. Everything was clean and the cabin has very rustic vibes. It’s on its own lot with a great back porch and bbq. Would highly recommend!
Quick stats about cottage rentals in Shandaken
Total rentals
50 properties
Nightly prices starting at
$140 SGD before taxes and fees
Total number of reviews
6.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- John Boyd Thacher State Park
- Taconic State Park
- Resorts World Catskills
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Hudson Highlands State Park
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Brotherhood, America's Oldest Winery
- Windham Mountain
- Villa Roma Ski Resort
- Opus 40
- Hunter Mountain Resort
- Thaddeus Hait Farm
- Plattekill Mountain