Guesthouse vacation rentals in Shandaken
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Top-rated guesthouse rentals in Shandaken
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Shandaken guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Long Eddy
4.97 out of 5 average rating, 145 reviewsThe Grange
Perfect for a secluded weekend away. House is very well kept. Grounds are very pretty. Would stay here again. Also Bobbie was very friendly and welcoming when we arrived.
Guesthouse in Tivoli
4.94 out of 5 average rating, 242 reviewsLight-filled guest cottage
i had a lovely time here. the cottage is serene and cozy, and the surrounding land is perfect for long runs or walks.
Guesthouse in Germantown
4.97 out of 5 average rating, 74 reviewsThe 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!
Guesthouse in Olivebridge
4.92 out of 5 average rating, 266 reviewsSweet Fern Cottage With Saltwater Pool
Meredith’s place is the perfect get away cottage. Private and very peaceful. The cottage is very cozy and has all the amenities listed. We met Meredith and Clara, her dog, the second day of our stay. Meredith is very sweet and suggested a few places we could visit near by. While we were talking, our dogs just ran around and play around the humongous backyard… What a delightful sight that was. Meredith also insisted that we pick herbs and vegetation from her garden and we did. They were amazing as well. There’s a few small bugs here and there but this was to be expected from a property quite deep into the mountains. Not a negative for us. Overall, this place is amazing. It gave us the rest we wanted and more. We will visit again when we have the chance. Thank you, Meredith, for letting us stay at your place!
Guesthouse in Jeffersonville
4.94 out of 5 average rating, 35 reviewsSamba 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!
Guesthouse in Jeffersonville
4.75 out of 5 average rating, 259 reviewsSweeping Mountain View From Catskills Farm Retreat
Great stay and a beautiful view. Cats were very friendly and greeted us right away even in the snow! Felt right at home while there, it was the perfect spot for a quiet weekend getaway.
Guesthouse in Mongaup Valley
4.98 out of 5 average rating, 397 reviewsGood Vibes Studio in the Woods
Absolutely beautiful time here Good vibes for sure. The host was super responsive and gave great recommendations. We got to visit baskakill vineyard, had great pizza from forage pizza, did some star gazing. Such an amazing time and we are looking forward to coming back!
Guesthouse in Swan Lake
4.95 out of 5 average rating, 309 reviewsBamboo House Retreat in Catskill
Had a lovely getaway from the city.. very peaceful. Just what I needed
Guest house rentals with a patio
Guesthouse in Hudson
5 out of 5 average rating, 44 reviewsHudson Countryside Guest Cottage w/Amazing Views
This was a beautiful property with amazing views minutes from downtown Hudson. Karen is an amazing host. The place was clean and even had pamphlets for recommendations around the location. And the view in morning was beautiful. I would recommend anyone looking at a trip in Hudson to stay here!
Guesthouse in Kerhonkson
5 out of 5 average rating, 31 reviewsCozy Guesthouse & Healing Vibes
Anne's place is delightful. There are cute little touches everywhere designed to make the place beautiful, though uncluttered, and to make your stay effortless and enjoyable. The pellet stove made everything even cosier. I LOVE her place and will hopefully be back to enjoy it again.
Guesthouse in Callicoon
5 out of 5 average rating, 65 reviewsR52Creekside one bedroom cottage
I have stayed here a few times now so I guess you can say it’s my home away from home. Randy is very friendly, and welcoming and gives great local recommendations. This place is exactly as pictured, a great escape from the city chaos that I am accustomed to. The attention to detail doesn’t go unnoticed. If you have a chance, stop by his store R52 home too! See you soon!
Guesthouse in High Falls
4.97 out of 5 average rating, 30 reviewsModern and warm guesthouse
We absolutely adore Denise’s place! As a former architect, I’m obsessed with the thoughtful design and meticulous details throughout the space. The woodwork is stunning, and every element feels intentional and well-crafted. The setting is private, serene, and perfect for leisurely strolls. It’s also conveniently located near trails and New Paltz, where we enjoyed great food and coffee. We’d love to return in the future!
Guesthouse in Bloomingburg
5 out of 5 average rating, 14 reviewsMondrian Manor
Mondrian Manor is a unique and delightful guesthouse. The interior is painted to evoke Mondrian style, as seen in the pictures, and there is original artwork through the spaces that add a touch of whimsy. Tracy is a fabulous host, communicating well and responsive to questions throughout. She has a binder with lots of information about outdoor activities, local eateries and activities. There was plenty of room for our family of 3 -- a couple plus teen. The space was comfortable and very clean. The kitchen was nicely equipped for cooking and eat-in dining (we did mostly coffee/tea and snack). There is a patio for sitting/eating if you are staying in warm weather. We stayed three nights and "commuted" to a retreat at Blue Cliff Monastery, which is just 7 minutes away by car. It's a perfect spot for having private personal space while on retreat, but easily getting back and forth to the monastery.
Guesthouse in Accord
4.92 out of 5 average rating, 109 reviewsTiny Horse Barn
We had a fantastic stay at the Tiny Horse Barn. The accommodations are so comfortable and homey with an artsy flair. Nicolette and Tim provided great info on the surrounding area restaurants. We will definitely return!
Guesthouse in Margaretville
4.9 out of 5 average rating, 10 reviewsRosa Guesthouse. - 10 Mins to skiing - private
Our stay at the Rosa Cabin was absolutely wonderful! Dean’s hospitality was above and beyond. The cabin was cozy, comfortable and roomy. Everything we needed was available to us in the cabin. Super close to many great restaurants and short drive to the ski mountain. I really look forward to staying here again!
Guesthouse in Kerhonkson
4.89 out of 5 average rating, 108 reviewsCozy Catskills Cottage
Richard had the guest cabin clean and warmed for our arrival. The ducks were beautiful and very friendly. Thank you Richard for having us!
Guest house rentals with a washer and dryer
Guesthouse in Kerhonkson
4.98 out of 5 average rating, 59 reviewsKerhamptons Hideaway in Heart of Hudson Valley
Vivi’s place was a great weekend getaway for us! The space was both beautiful (very high end and looks just like the pictures) and comfortable (nice bedding and towels) and had all the amenities for a cozy winter stay! She was very responsive, answering our messages within minutes, and had some great local recommendations for dinner and drinks.
Guesthouse in Accord
5 out of 5 average rating, 20 reviewsGame 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.
Guesthouse in Gardiner
4.99 out of 5 average rating, 167 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
The space was clean, comfy, and in a great location with easy access to nearby towns. Bill also communicated clearly and had great recommendations.
Guesthouse in Clinton Corners
4.97 out of 5 average rating, 32 reviewsStunning 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
Guesthouse in East Meredith
4.98 out of 5 average rating, 129 reviewsLily 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!
Guesthouse in Parksville
4.94 out of 5 average rating, 33 reviewsWonderful 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!
Guesthouse in Stanfordville
4.93 out of 5 average rating, 179 reviewsEco 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.
Guesthouse in Hudson
5 out of 5 average rating, 27 reviewsSerene one bedroom guest house with fireplace.
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.
Quick stats about guesthouse rentals in Shandaken
Total rentals
30 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
1.3K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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