Guesthouse holiday rentals in Shandaken

Find and book unique guesthouse rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Shandaken guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Tivoli
4.94 out of 5 average rating, 255 reviews

Light-filled guest cottage

JohnRating, 5 stars2 weeks ago
An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!
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
Guesthouse in Hudson
4.99 out of 5 average rating, 83 reviews

Cozy cottage on Angus Farm, 15 mins from Hudson.

LauraRating, 5 stars2 months ago
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!
Superhost
Guesthouse in Mount Vision
5 out of 5 average rating, 5 reviews

Cooperstown All Star Village & Dreams Park House

LydiaRating, 5 stars2 weeks ago
The pictures don’t do it justice. In the pictures it looks dark but there is a lot of natural light. Michael was great, he made sure we had all the instructions and even called me directly to make sure my trip would go smoothly. I really appreciated the cleanliness of the place. It has always been my biggest fear. Thank you so much for providing water and coffee that was sweet. We were there for Cooperstown Dream Park and the drive was not far. It is beautiful and peaceful. Thank you for the hospitality.
Superhost
Guesthouse in Saugerties
4.86 out of 5 average rating, 139 reviews

Private Guesthouse in Saugerties

ChristineRating, 5 stars1 month ago
This is I believe our 4th year staying at Sheena’s place in Saugerties the same weekend in May for a hockey tournament. The space is walking distance to town and the rink so we can enjoy the nightlife. The place is always immaculate, with fresh lilacs on table, water tea and coffee available for the morning. Bonus washer and dryer especially helpful during the hockey tournament. Sheen is always super responsive and flexible during our stays. Highly recommend Sheena’s place.
Top Guest favourite
Guesthouse in Jeffersonville
4.94 out of 5 average rating, 35 reviews

Samba Inn - Deck House

Shaniquah & DavidRating, 5 stars8 months ago
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!
Superhost
Guesthouse in New Paltz
4.6 out of 5 average rating, 228 reviews

The Cottage - New Paltz

JeanRating, 5 stars1 month ago
A small place, but a great stay for a couple and their dog ( like us). A feeling of being in the country, but still close to town and attractions.
Superhost
Guesthouse in Stormville
4.97 out of 5 average rating, 175 reviews

Hudson Valley Cottage with Pond Access

ChelseaRating, 5 stars2 months ago
If you're looking for a private retreat in a gorgeous setting, this is your place. The property is stunning, super walkable grounds, and a gorgeous back patio. S.A. is a super host, and when we ran into an issue, he was quick to respond and help. We recommend this place, and intend to stay again in the future.

Guesthouses with a patio

Top Guest favourite
Guesthouse in Saugerties
4.97 out of 5 average rating, 39 reviews

Avalanche Farms private Guesthouse w/Stream Access

SimoneRating, 5 stars2 weeks ago
Jessica’s place was the perfect choice for a quick weekend getaway to Woodstock. The space was sparkling clean and well stocked with extra linens and kitchen items. The property was peaceful and serene and a dream to wake up too in the morning. Highly recommend!! Jessica was able very responsive and check in and out was a breeze. 10/10!
Guest favourite
Guesthouse in Saugerties
4.97 out of 5 average rating, 65 reviews

Little Bliss Pond House

JackRating, 5 stars3 weeks ago
I chose The Little Bliss Pond House as my proposal site. The location was absolutely breathtaking and exactly what I imagined. Cara was extremely responsive and helpful during the entire process. I would highly recommend The Little Bliss Pond House to anyone looking for a quaint and peaceful location surrounded by the best nature has to offer. About a 10 minute drive to some great restaurants and shops in Saugerties, The Little Bliss Pond House is the perfect escape for a weekend. 10/10. Thanks Cara!
Top Guest favourite
Guesthouse in Kerhonkson
5 out of 5 average rating, 36 reviews

Cozy Guesthouse & Healing Vibes

WendyRating, 5 stars1 month ago
Quaint wonderful place filled with nearly every cooking need -even a carton of local eggs! Also Anne’s love of healthy and natural products was evident through shampoos, hand creams, and the like for our use. Finally Anne was so responsive to every question or need, usually within a minute! We will return. Please know that Google gps wrongly stated that Anne’s address was across the road where a school sits.
Top Guest favourite
Guesthouse in High Falls
4.97 out of 5 average rating, 34 reviews

Modern and warm guesthouse

SueRating, 5 stars4 weeks ago
Loved our stay and hope to come back in the future! Denise's place is beautifully designed and has lots of thoughtful touches. The house is less than a 10 min drive from Accord and 15 min from New Paltz, so there was a nice balance of nature/privacy with easy access to restaurants and things to see. Denise was very helpful and friendly, and check in was smooth and easy.
Top Guest favourite
Guesthouse in Wallkill
5 out of 5 average rating, 54 reviews

Millie's Inn

AlexRating, 5 stars3 weeks ago
Millie’s Inn exceeded all of our expectations. It’s private, peaceful, comfortable, clean and so beautifully designed. Jackie & Lenny are responsive and dedicated hosts who made sure we had everything we needed our entire stay. We would stay here again and recommend it to anyone in a heartbeat.
Top Guest favourite
Guesthouse in West Hurley
5 out of 5 average rating, 43 reviews

Unequalled Reservoir Mtn Views-Private, Affordable

Becky And MaryRating, 5 stars3 weeks ago
We had an amazing stay here. Originally booked for two nights but extended for a third because we liked it so much. Perfect location, very close to Woodstock and shopping, restaurants, fun things to see and do. The unit was impeccably clean and well-maintained, spacious, bright and cozy. And the view is to-die-for. The most stunning and picturesque scenery I’ve experienced in years - and we live in the Hudson Valley! It was the perfect Memorial Day getaway. Plus the properly manager was very communicative and helpful with all questions we had. Would definitely recommend.
Guest favourite
Guesthouse in Accord
4.92 out of 5 average rating, 124 reviews

Tiny Horse Barn

LisaRating, 5 stars1 month ago
My husband and I arrived late, around 9:30pm, because we had commuted after work in NYC. Everything was impeccable. The home is perfect in some many ways. We felt very comfortable and got an amazing night's sleep. The following more we had to head out early to pick our daughter up from Binghamton. She stayed with us on our second night. Nicolette's and Tim's Tiny Horse Barn is so perfect. It is exact amount of space we needed. Even though the space is space, there were 5 tissue boxes in perfect locations. This may seem a small thing to some. But if you have allergies, it is SO appreciated. The kitchen was equipped with keurig coffee pods, creamers, sugar, tea kettle and more than everything we needed. Equally the bathroom was perfect. The beds were super comfortable as was the temperature. There were plenty of great restaurants nearby. The attention to detail is amazing. Everywhere there are little hints of horses, but not in an overwhelming way. We actually are having book sent :)
Guest favourite
Guesthouse in Margaretville
4.92 out of 5 average rating, 13 reviews

Rosa Guesthouse - close to everything - private

TylerRating, 5 stars2 weeks ago
We loved this cottage in Margaretville. It was a perfectly peaceful launching point for our adventures exploring the catskills. The hosts gave a lot of really great recommendations for things to explore in the area. Fantastic stay!

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in Kerhonkson
4.98 out of 5 average rating, 64 reviews

Kerhamptons Hideaway in Heart of Hudson Valley

LauraRating, 5 stars1 week ago
This stay offers a lovely home and view. Photos in the advertisement are accurate & communication was easy with the airbnb app. Upon our arrival we looked out back to see a young male deer in the adjacent field nibbling on his meal. Welcoming scene. Everything in the home is very clean; bed is a comfy king; there is one television in the livingroom with you tube available, but no live tv, so bring your Hulu/Netflix info or Firestick if you're a tv enthusiast. We we're in the area for a family wedding so that wasn't impt to us. We felt very comfortable & would recommend this home for any single or couple looking for a stay in the area.
Top Guest favourite
Guesthouse in Gardiner
4.99 out of 5 average rating, 175 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

GretchenRating, 5 stars1 month ago
Great experience! 2 wineries within 1 mile. Close to great hiking. William, was very accommodating with check in & check out time. Would highly recommend staying here. Very cute , clean and comfortable with get amenities.
Top Guest favourite
Guesthouse in East Meredith
4.98 out of 5 average rating, 132 reviews

Lily Pad by the Ponds

MadelineRating, 5 stars3 weeks ago
The location is very peaceful and serene and the hosts are very thoughtful. It was a wonderful stay, thank you so much for having us!
Guest favourite
Guesthouse in Windham
4.97 out of 5 average rating, 102 reviews

Little Bear’s Cottage Great location, cozy & cute

kathyRating, 5 stars1 month ago
This is our 2nd time at Marta's place. We returned because the location and accessibility is perfect. Everything is as stated in the post and Marta is a very responsive and friendly host. We will be back!!
Top Guest favourite
Guesthouse in Woodstock
5 out of 5 average rating, 12 reviews

Modern & Private Cottage Minutes From Woodstock

WilsonRating, 5 stars3 weeks ago
We had a great time! Great location close to the center of Woodstock — very functional and clean space, everything worked perfectly. Kitchen was well equipped too! Overall very well thought out and perfect spot in Woodstock :)
Top Guest favourite
Guesthouse in West Hurley
5 out of 5 average rating, 70 reviews

Woodstock Rural Villa: Tree Top HideAway

YiyingRating, 5 stars4 months ago
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!
Guest favourite
Guesthouse in Bloomville
5 out of 5 average rating, 57 reviews

Catskill Treetop Retreat

ElizabethRating, 5 stars3 weeks ago
The home is exactly as seen in the pictures, it was spotless, cozy, and welcoming. Everything we could have possibly needed was thoughtfully provided. Little touches—like treats and water—made us feel so special. Our host was absolutely wonderful—responsive, kind, and genuinely invested in making our stay comfortable. It felt less like a transaction and more like being welcomed by a friend. They gave us great recommendations for nearby cafes, hidden gems, and things we might have missed otherwise written in their binder. The binder also information on the history of the area and their journey which was a nice touch. This is a great writers retreat!
Top Guest favourite
Guesthouse in Stanfordville
4.93 out of 5 average rating, 181 reviews

Eco Cottage in the Woods

KymRating, 5 stars2 weeks ago
The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!

Quick stats about guesthouse rentals in Shandaken

  • Total rentals

    30 properties

  • Nightly prices starting at

    $84 NZD 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

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Ulster County
  5. Shandaken
  6. Guesthouse rentals