
Guesthouse vacation rentals in Shandaken
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Top-rated guesthouses in Shandaken
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Popular amenities for Shandaken guesthouses
Family-friendly guesthouses

Light-filled guest cottage
The cottage is utterly sweet, beautiful, timeless, and well cared for. A truly perfect place to rest and restore. I was reminded of the magic of being in a space that feels just good and right. I adored the upper bedroom, with its bed and bath and sweet windows overlooking snowy fields. The linens are lovely and the kitchen has everything you need. I would stay here anytime visiting tivoli!

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!

The Cottage - New Paltz
What a fantastic find!! This place was well worth the money, especially since they accommodate our 2 dogs with no weight limits. I read many reviews state a smell with the water and we did not notice one at all, the house was very clean and had everything you could think of and then some. Very nice and cozy and not far from town to go and grab some great food! Would definitely stay again

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!

Sweeping 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.

The White Barn: A Bright Barn Loft in the Country
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!

Good Vibes Studio in the Woods
Love the vibe! Our third time there as a couple and we love the privacy and decor! Cannot wait to stay there again during concert season!!
Guesthouses with a patio

Hudson 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!

Cozy 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.

R52Creekside one bedroom cottage
Wonderful stay!! We had a great weekend getaway with our pooch. The space is so charming, beautifully designed, and super fresh and clean feeling. Loved the thoughtful snack basket, phone chargers, organic toilet paper, delicious bags coffee of coffee, fully stocked pantry with every utensil you will need! Randy and Keith were so sweet and welcoming over Airbnb. Really felt lucky to have found this spot. Tons to eat and do in this area too. Everything is under 10 mins, whichever direction.

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 ❤️✨

Mondrian 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.

Tiny Horse Barn
One of the best airbnbs I have rented! The place is exquisite. I specially liked the design of the house. It’s an experience! It had all the amenities to cook, grill and relax! I would highly recommend if you are looking for a relaxing stay and enjoy nature!

Rosa Guesthouse - close to everything - 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!

Cozy Catskills Cottage
Had a great stay. Would definitely stay again in the future! The duck pond was great and the ducks were very cute. Very quiet and nice property.
Guesthouse rentals with a washer and dryer

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.

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!

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!

Woodstock Rural Villa: Tree Top HideAway
We had a wonderful stay up in Woodstock for the Presidents Day weekend. We went to nearby Bellayre for skiing and sampled the wonderful restaurants in Woodstock. Leslie and Colin’s place was a perfect launch pad and so totally comfortable and cosy. It had everything we needed - even eggs, butter and milk in the frig for breakfast! Leslie and Colin were very attentive hosts and we always felt well taken care of during our stay. We enjoyed the wood stove!

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!
Quick stats about guesthouse rentals in Shandaken
Total rentals
30 properties
Nightly prices starting at
$71 CAD 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
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
- Taconic State Park
- The Kartrite Resort & Indoor Waterpark
- Villa Roma Ski Resort
- Opus 40
- Thaddeus Hait Farm
- Brotherhood, America's Oldest Winery
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Resorts World Catskills
- Plattekill Mountain
- Hudson Highlands State Park
- Zoom Flume
- Bear Pond Winery
- John Boyd Thacher State Park
- Howe Caverns