Guesthouse vacation rentals in Shandaken

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Popular amenities for Shandaken guesthouse rentals

Family-friendly guest house rentals

Guest favorite
The rustic cottage is illuminated against a dusky pink and purple sky at sunset, with warm light spilling from its windows. Surrounded by trees that are beginning to lose their leaves, the setting evokes a peaceful, countryside atmosphere.
Guesthouse in Tivoli
4.94 out of 5 average rating, 247 reviews

Light-filled guest cottage

EricaRating, 5 stars1 month ago
Thank you for a cozy stay! We loved the preserve across the street and waking up to the sound of birds and the country.
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 stars5 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 stars1 week 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!
Guest favorite
The cottage exterior features a warm red facade, surrounded by lush greenery. A wooden deck with railing invites relaxation, offering shaded seating under the retractable awning. Nearby, a mix of shrubs and ornamental grasses enhances the natural landscape.
Guesthouse in Olivebridge
4.93 out of 5 average rating, 267 reviews

Sweet Fern Cottage With Saltwater Pool

ChristineRating, 5 stars5 months ago
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!
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 stars6 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, 224 reviews

The Cottage - New Paltz

RobinRating, 5 stars3 weeks ago
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!
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
4.98 out of 5 average rating, 172 reviews

Hudson Valley Cottage with Pond Access

JamieRating, 5 stars6 months ago
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!
Top guest favorite
A spacious studio is highlighted by large windows allowing natural light to flow in. A cozy sleeping area features a queen bed adorned with a colorful blanket. A foosball table adds a playful element, while rustic wooden paneling and artistic wall decor create an inviting atmosphere.
Guesthouse in Mongaup Valley
4.99 out of 5 average rating, 405 reviews

Good Vibes Studio in the Woods

RedRating, 5 stars3 weeks ago
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

Top guest favorite
The exterior of a newly renovated guest house is captured on a clear day. The white structure features a dark roof and is surrounded by well-maintained greenery and bushes. A paved walkway leads to the entrance, while trees and a bright blue sky create a tranquil setting.
Guesthouse in Staatsburg
5 out of 5 average rating, 9 reviews

Aberdeen Farm

RobertRating, 5 stars5 months ago
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.
Top guest favorite
A dining area is visible with two black chairs surrounding a glass table. A cozy seating space with a light-colored armchair is situated in the corner, while large glass doors open to a spacious covered patio, surrounded by lush greenery.
Guesthouse in Kerhonkson
4.98 out of 5 average rating, 60 reviews

Kerhamptons Hideaway in Heart of Hudson Valley

BrianRating, 5 stars2 months ago
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!
Top guest favorite
Guesthouse in Accord
5 out of 5 average rating, 20 reviews

Game House in Historic Accord

SusieRating, 5 stars4 months ago
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.
Top guest favorite
A lush green field extends towards the horizon, framed by clusters of trees. The sky is filled with varying shades of clouds, reflecting a soft light from the setting sun. The peaceful rural landscape evokes a sense of tranquility.
Guesthouse in Gardiner
4.99 out of 5 average rating, 174 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

PatriciaRating, 5 stars1 month ago
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.
Top guest favorite
Guesthouse in Kerhonkson
5 out of 5 average rating, 33 reviews

Cozy Guesthouse & Healing Vibes

DeborahRating, 5 stars1 week ago
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.
Top guest favorite
The exterior of the modern structure features large windows and a sloped roof. A wooden deck is highlighted with two red chairs and decorative planters filled with greenery and flowers. Soft sunlight illuminates the space surrounded by trees.
Guesthouse in Callicoon
5 out of 5 average rating, 72 reviews

R52Creekside one bedroom cottage

Michael & AndreaRating, 5 stars1 week ago
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.
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, 31 reviews

Modern and warm guesthouse

EstefaniaRating, 5 stars3 months ago
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 ❤️✨
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, 119 reviews

Tiny Horse Barn

LindaRating, 5 stars2 weeks ago
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

Guest favorite
A modern cabin is nestled among lush trees, featuring large windows that allow natural light to fill the interior. A wooden deck extends from the entrance, providing a welcoming outdoor space surrounded by greenery.
Guesthouse in Clinton Corners
4.97 out of 5 average rating, 32 reviews

Stunning lake side modern barn in Hudson Valley

EmilyRating, 5 stars5 months ago
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
Top guest favorite
Guesthouse in East Meredith
4.98 out of 5 average rating, 129 reviews

Lily Pad by the Ponds

NickRating, 5 stars6 months ago
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!
Top guest favorite
A spacious deck adorned with two red Adirondack chairs invites relaxation. Potted flowers line the deck, while two lounge chairs are placed on the lush lawn. The backdrop features tall forest trees, creating a serene outdoor atmosphere.
Guesthouse in Woodstock
5 out of 5 average rating, 10 reviews

Modern & Private Cottage Minutes From Woodstock

RobertRating, 5 stars5 months ago
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.
Guest favorite
Guesthouse in Parksville
4.94 out of 5 average rating, 33 reviews

Wonderful getaway place in the Catskills!

JayRating, 5 stars4 months ago
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!
Top guest favorite
A pathway lined with grass leads to a charming red farm guest house. Towering trees provide shade, while a green hillside is visible in the background. A clear blue sky adds to the serene outdoor setting.
Guesthouse in Wappingers Falls
5 out of 5 average rating, 8 reviews

1723 Guesthouse

DoniRating, 5 stars2 months ago
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
Guest favorite
Guesthouse in Stanfordville
4.93 out of 5 average rating, 179 reviews

Eco Cottage in the Woods

SusanRating, 5 stars6 months ago
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.
Guest favorite
A sleek, modern walk-in shower features white subway tiles and a decorative border. A handheld showerhead is mounted above, and a stainless steel shower caddy is attached to the wall for convenience. The clean design emphasizes simplicity and functionality.
Guesthouse in Red Hook
4.94 out of 5 average rating, 93 reviews

Private Cottage, Walk to Restaurants and Shops

beccaRating, 5 stars3 months ago
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!
Top guest favorite
A covered terrace features a circular area rug and comfortable seating with plush cushions. A glass table is positioned at the center, while a view of the river and surrounding trees is visible through the railing, enhancing the outdoor experience.
Guesthouse in Ulster Park
4.99 out of 5 average rating, 415 reviews

Escape to a Sleek, Serene Studio on the Riverbank

NinaRating, 5 stars1 week ago
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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