Guesthouse vacation rentals in Shandaken

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Popular amenities for Shandaken guesthouse rentals

Family-friendly guest house rentals

Guest favorite
A light-filled living space features rustic white walls and wooden floors. A cozy soapstone stove stands beside a small seating area with a wicker chair and a couch. The doorway leads to a wooden-paneled area with hanging coats and boots, inviting a sense of home.
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 favorite
A light-filled living area features a navy loveseat and a round dining table with two wooden chairs. The space is anchored by a patterned area rug on warm wood flooring. A door opens to a view of the greenery outside, inviting natural light indoors.
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 favorite
Aerial view of a cottage set on a farm, surrounded by expansive green fields and trees with autumn foliage. A pond reflects the landscape, and a winding path leads to the nearby cottage, which is positioned amidst the serene countryside.
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
A cozy living area features a comfortably upholstered sofa paired with a stylish armchair. A cowhide rug lies on the warm hardwood floor, while a contemporary side table and a console table provide functional space. Art is displayed on the walls, enhancing the room's decor.
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 favorite
An outdoor deck area features a round table accompanied by four wrought-iron chairs. Sunlight casts intricate shadows against the wall and the floor, enhancing the cozy atmosphere. A planter with flowers is positioned nearby, adding a touch of greenery to the space.
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
A cozy living area is highlighted by a blue futon and an inviting patterned bench. A round white table with metal chairs is centered, while natural light filters through large windows. Decorative pendant lights add charm to the open space, creating a welcoming ambiance.
Guesthouse in New Paltz
4.6 out of 5 average rating, 229 reviews

The Cottage - New Paltz

JenniferRating, 5 stars1 day ago
Comfortable and cozy stay. Our dogs were quite welcome. Our host was always available to answer questions. We had a lovely welcome basket on arrival which was a welcome surprise. A perfect location for our stay.
Superhost
A charming cottage exterior is framed by lush greenery, featuring large front glass doors and a sloped roof. Potted flowers adorn the entrance, while a shaded sitting area with comfortable chairs is visible beside the pathway, inviting relaxation in a serene setting.
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.
Top guest favorite
The exterior of the guest house is shown alongside a wooden chicken coop. The house features large windows and a red roof. Lush green grass surrounds the area, with hints of autumn foliage visible on nearby trees.
Guesthouse in Forestburgh
4.97 out of 5 average rating, 422 reviews

Guesthouse On 1879 Farm. Hot tub and hiking

StacyRating, 5 stars1 week ago
Hidden gem. Really appreciated the countryside accommodation. The hot tub was nice and hot and we enjoyed a fire right after. The stores were in a close enough proximity if needed. My fiancé was skeptical as it’s right next to another property but we had are own space and we were not disturbed. Also we enjoyed the fresh eggs and being able to bring our fur babies.

Guest house rentals with a patio

Guest favorite
The exterior of a rustic cottage is displayed, featuring a weathered wood facade and large windows. A spacious wooden deck leads to steps designed for relaxation. Potted plants are positioned at the entrance, with natural light illuminating the area.
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 favorite
The exterior of the cottage is shown, featuring a white siding and multiple windows that invite natural light. A well-kept green lawn surrounds the building, complemented by mature trees in the background. The peaceful setting is enhanced by the clear sky.
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 favorite
A modern guesthouse features a dark exterior with large windows, surrounded by trees. A stone patio area is equipped with two outdoor chairs and a firepit, accompanied by neatly stacked firewood. Landscaping includes green grass and flowering plants, creating a serene outdoor setting.
Guesthouse in High Falls
4.97 out of 5 average rating, 34 reviews

Modern and warm guesthouse

SueRating, 5 stars1 month 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 favorite
An open-concept area features warm wood flooring and soft lighting from hanging lamps. A kitchen space is visible with a small island equipped with seating. A spacious bed is situated in the corner, dressed in patterned linens. Large windows allow natural light to brighten the room.
Guesthouse in Wallkill
5 out of 5 average rating, 54 reviews

Millie's Inn

AlexRating, 5 stars4 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 favorite
A panoramic view showcasing the Ashokan Reservoir surrounded by lush greenery. The clear blue sky is dotted with soft clouds, while trees frame the scene, creating a tranquil and peaceful setting.
Guesthouse in West Hurley
5 out of 5 average rating, 43 reviews

Unequalled Reservoir Mtn Views-Private, Affordable

Becky And MaryRating, 5 stars4 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 favorite
An open living space is illuminated by natural light from multiple windows, featuring a cozy sofa, wooden coffee table, and a dining area with metal chairs. A spiral staircase leads to a loft space, while a door opens to a private outdoor deck.
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 :)
Top guest favorite
A charming studio guesthouse is depicted, featuring a mix of light green and rustic wooden siding. A bright red door contrasts with the exterior. Lush landscaping includes small trees and decorative stones. The inviting entrance is framed by a clear blue sky and surrounding greenery.
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 favorite
A cozy living area features a large leather sofa and a stylish coffee table. Two large glass doors open to a spacious deck, allowing natural light to brighten the room. A decorative light fixture hangs from the ceiling, and a warm wooden floor complements the overall design.
Guesthouse in High Falls
4.9 out of 5 average rating, 41 reviews

Clove Casita on Mohonk Preserve

AmandaRating, 5 stars2 weeks ago
We really enjoyed staying at the casita. It was beautifully decorated, clean, and comfy. We enjoyed New Paltz and the outdoor activities in the area. Highly recommend staying here for a fun weekend getaway!

Guest house rentals with a washer and dryer

Top guest favorite
A flowing stream winds through a green landscape, framed by trees with budding leaves. The visible water cascades over rocks, creating ripples in the surface. Various shades of green and the gentle movement of water highlight the natural beauty of the area.
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!
Top guest favorite
A spacious outdoor deck wraps around the side of the house, surrounded by lush greenery. Light-colored railings and planters flank the area, offering a serene space for relaxation. The sloped yard enhances the natural beauty, complemented by the shade of surrounding trees.
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 favorite
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 favorite
A spacious gazebo with wooden beams overlooks a serene pond. Adironack chairs are arranged for seating, and a small table is centered on the deck. A vibrant rug adds color to the wooden floor, while greenery surrounds the tranquil setting.
Guesthouse in East Meredith
4.98 out of 5 average rating, 133 reviews

Lily Pad by the Ponds

DonaldRating, 5 starstoday
Very friendly and responsive owners.Very clean.Beautiful setting on a pond.Washer and dryer came in handy. Highly recommend
Guest favorite
A well-maintained outdoor space is framed by wooden fencing and lush greenery. A round table is centered on a wooden deck, accompanied by two folding chairs. Soft lighting from above adds a gentle ambiance, creating an inviting atmosphere for relaxation.
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 favorite
Guesthouse in Woodstock
5 out of 5 average rating, 12 reviews

Modern & Private Cottage Minutes From Woodstock

WilsonRating, 5 stars4 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 favorite
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 favorite
A red picnic table is situated in a natural setting, surrounded by lush green foliage. The area features a gravel surface and several wooden stools nearby, providing a space for relaxation and outdoor dining.
Guesthouse in Bloomville
5 out of 5 average rating, 58 reviews

Catskill Treetop Retreat

MayaRating, 5 stars1 day ago
Just took a quick work trip up to the Catskills and needed a place to rest. This place was perfect. Clean and beautiful space, with everything I needed and more! Chandi was super responsive and helpful. I will be back!

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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