
Guesthouse vacation rentals in Shandaken
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Top-rated guesthouse rentals in Shandaken
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Popular amenities for Shandaken guesthouse rentals
Family-friendly guest house rentals

Light-filled guest cottage
Thank you for a cozy stay! We loved the preserve across the street and waking up to the sound of birds and the country.

The Guest House
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!

Cozy cottage on Angus Farm, 15 mins from Hudson.
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!

Sweet Fern Cottage With Saltwater Pool
We were 3 adults, 1 child and 1 dog and found the Airbnb to be very nice for a weekend! We met Meredith and her dog Clara who was very friendly. The Airbnb had everything we needed in a rustic setting, the beds were comfortable. Unfortunately the stove wasn’t working during our stay, but Meredith was apologetic and warned us a few days beforehand. She left some delicious bagels and cream cheese in the fridge for us which we appreciated!

Samba Inn - Deck House
We can’t say enough about our stay. Very cozy and actually quiet. Everything in the listing was accurate and we got to meet Tim who was very friendly and welcoming. Don’t hesitate to book, you will be very pleased!

The Cottage - New Paltz
Stephen was a wonderful responsive host. We had one concern about the stove and he responded immediately with very helpful guidance and, without us asking, sent a small courtesy refund for the inconvenience. We very much look forward to staying at this darling cottage again and walking the rail trail, and hiking in the beautiful Minnewaska State Park Preserve! Highly recommended!

Hudson Valley Cottage with Pond Access
This bungalow was a magical place to spend an autumn weekend visiting family and the beautiful Hudson valley area. We enjoyed morning walks around the pond with our pup and our coffee. Wish we had time to use the fire pit! Hammocks and bed was comfy, shower and kitchen were clean and lovely! Thanks so much a for a great stay! Would certainly recommend!

Good Vibes Studio in the Woods
absolutly amazing stay, super nice hostess we loved the decorations and they provided alot of things and services, also the epiq peoples book was a really cute idea. we will forsure be coming again soon!
Guest house rentals with a patio

Aberdeen Farm
My family and I stayed at Kyle’s the night before we moved into our new home roughly 10 mins from his place. We were moving from out of state, with a baby, and the normal struggles that come with and big move. Kyle was very understanding, kind, friendly, and accommodating. I highly recommend this place.

Kerhamptons Hideaway in Heart of Hudson Valley
Me and my partner loved our stay. Vivi was super responsive and check in/out was a breeze. We got hit with snow the night before our last day, but Vivi lets us know that they plowed the snow early in the morning so we wouldn’t get stuck. We were so appreciative of that! I highly recommend booking your stay here!

Game House in Historic Accord
This was the perfect place for us to stay for Thanksgiving in Accord with family. Although attached to Jolle's house, it was entirely private with its own entrance and parking area. The cottage is pristine, very nicely put together and so very comfortable. Underfloor heating made it even cosier on a very wintery snowy Thanksgiving Day! Jolle's very welcoming gift of local chocolates, a bottle of wine and coffee in the freezer made us feel welcome. All the local recommendations were helpful and we all decided that this was the place to come back to next time we return to Accord! Highly recommended.

Red Barn Retreat - Shawangunk Mountains Getaway
This place was a perfect weekend get away for myself and husband. Plenty of space for the two of us. The place was nicely, decorated and fully furnished with accessories if you wish to cook. I enjoyed the spaces between the outside patio as well as the hot tub. Bill was great with giving suggestions of local places, even though I was a local myself.. if you’re looking for a quiet getaway this is your place.

Cozy Guesthouse & Healing Vibes
Lovely, well-appointed cottage with a little creek running through the yard. Sunlight streams into every room. Annie’s pantry was the most thoroughly stocked that we have ever experienced. Still, she left a basket of all the fixins for s’mores. The piano was an added bonus. We’d absolutely return.

R52Creekside one bedroom cottage
We had a wonderful time, and despite getting a few inches of snow on our 'spring getaway', the cabin was nice and cozy. There's a lot of charm in the old Catskills homes, but sometimes nothing beats a brand new place. We were surprised it's two years old, the cabin is spotless and looks brand new. Plenty of room for the two of us and a dog. We appreciated the extra towels for the dog given the weather. Hope to come back in more seasonable weather and take advantage of the wonderful back yard and drink our coffee on the deck next time. Despite being right on Route 52, it was still nice and quiet and relaxing.

Modern and warm guesthouse
Denise’s place was an amazing gateway from the craziness of the city. If somebody wants to escape and feel the quiet of the nature please book this right away. My boyfriend and me enjoyed this place a lot for the only two days we stay. Thanks Denise’s ❤️✨

Tiny Horse Barn
this is a lovely sweet cozy place, perfect for me and my teen. they loved the cozy loft (though the mattress is on the short side but still had a great night's sleep). I enjoyed sitting on the quiet, scenic porch to relax a bit. lovely place! thank you
Guest house rentals with a washer and dryer

Stunning lake side modern barn in Hudson Valley
If I could give more stars, I would-- not just for the stay but to also represent Cheryl as a host and human! The stay was absolutely amazing-- the house was gorgeous, the property was exceptional. The location is great given it can satisfy whatever you're looking for: quiet, peaceful, great downtown and food scene, hikes if you'd like, etc. Cheryl quickly gave so many recommendations on local hikes, things to do, and eateries-- she covered all the bases without even being asked. She is also incredibly responsive, kind, and generous. I truly don't have enough great things to say, and I'm hoping to stay here annually with my partner. Our hearts have stayed at Knight Road <3

Lily Pad by the Ponds
Fantastic place for a weekend getaway! Gail is a lovely host and very responsive. You have one room as shown in the picture, and a separate bathroom with a shower, towels, and toilets. It's a 20 second walk away from the main room. We visited during autumn and the trees were beautiful. You can use a grill and fireplace, as well as a boat on the small lake. Can highly recommend!

Modern & Private Cottage Minutes From Woodstock
The house is great. Fully renovated and all new appliances. Spacious, clean and everything you could want. This was perfect for me, my wife, little baby and our dog. The back yard was perfect for our city dog to get a little country time.

Wonderful getaway place in the Catskills!
I had such a great stay at Yelena's charming little house! It’s small but super cute, making it the perfect place for three people. Everything was cozy and well-appointed, and it felt like a home away from home. The location is also fantastic—there are some adorable spots nearby to explore, with plenty of cute cafes and shops. Yelena and Katia were friendly and responsive, and the place had everything we needed for a comfortable stay. I highly recommend it to anyone looking for a quaint and relaxing getaway!

1723 Guesthouse
We had a great stay. The host was super helpful. Always responded quickly. Even had goodies waiting for us. The house was warm and cozy even in the middle of February. They had the snow cleared before we arrived. It was not a problem. Though the house has some quirks of an older farmhouse, it was nice and very comfortable. Be aware that one of the 3 beds is downstairs by the entrance not in a private room. Wasn’t a problem for us though. The others are upstairs in 2 private rooms. The kitchen has little in the way of cooking supplies. Would have been nice to have more pots/pans and oil, salt etc. since we wanted to cook. The house is in a very beautiful spot attached to a gorgeous country home. Lovely views of barns and fields. It was also very quiet. We slept well. No noise at night or early mornings. Overall good experience

Eco Cottage in the Woods
Upon entry, my architect husband said "Cute Cottage; Susan you did it again." Plenty of room for a couple in their mid-seventies, and a Millennial daughter. The cottage is very well insulated such that I didn't have to run the heat except for fifteen minutes at bedtime in mid-October, yet there is a big south-facing sliding door in each of the rooms where the sun and moon shines through. Beautiful woodland falls away from the cottage and small patio beyond the sliding doors, and moonlight is magic on all the leaves. If we had more time we would have investigated the many books in the shelving. We will find excuses for coming back to the area and will stay here again.

Private Cottage, Walk to Restaurants and Shops
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!

Escape to a Sleek, Serene Studio on the Riverbank
I loved my stay here. I came up solo to work, sleep and relax. The unit itself is wonderful if you gravitate toward sunlight and thoughtful design. The mattress is fantastic and the place has everything you could hope for. The view is stunning and the outdoor space is adorable with plenty of place to spread out both indoors and outdoors. It is peaceful and quiet. You will sleep like a rock. The studio was spotless. There is some hiking options a short walk away and Kingston is about ten minutes or less (the waterfront section). Shannon is an ideal host and has thought of everything. Do not hesitate to book this if you want to relax and have a million dollar river view in a stylish and comfortable studio. I hope to be back for sure!
Quick stats about guesthouse rentals in Shandaken
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- John Boyd Thacher State Park
- Zoom Flume
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Opus 40
- Howe Caverns
- Bash Bish Falls State Park
- Thaddeus Hait Farm
- Walkway Over the Hudson State Historic Park
- Plattekill Mountain
- Hudson Highlands State Park