Guesthouse vacation rentals in Shandaken

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Popular amenities for Shandaken guesthouses

Family-friendly guesthouses

Guest favourite
Guesthouse in Tivoli
4.94 out of 5 average rating, 245 reviews

Light-filled guest cottage

ElizabethRating, 5 stars1 week ago
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!
Guest favourite
Guesthouse in Germantown
4.97 out of 5 average rating, 74 reviews

The Guest House

StephenRating, 5 stars4 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!
Guesthouse in New Paltz
4.59 out of 5 average rating, 221 reviews

The Cottage - New Paltz

Bara & FranciscoRating, 5 stars2 months ago
The location of this rental is really fantastic, we literally didn't know what to do first. We were looking for a quiet place for our dog away from the New Years firework and this was definitely it. There was very few going off and only 30minutes after midnight and that was it which is a big difference from Brooklyn. However we won't be renting it again for following reasons: 1. the property is literally ON THE ROAD- so close- which is pretty busy and cars go very fast, our kids are big enough (8 & 11) and our dog is off leash dog w perfect recall but when you make the fire in front of the house at night - it's so dark everywhere no lights around the road - need to always make sure your pup doesn't wander off that direction so you need to be pretty alert the whole time. 2. the land under the house is VERY wet - all the time. My Sperry's broke in the beginning of my trip so when I walked the dog on the field in front of the house - and also for the kids to run around - it's so wet.
Guest favourite
Guesthouse in Olivebridge
4.93 out of 5 average rating, 267 reviews

Sweet Fern Cottage With Saltwater Pool

ChristineRating, 5 stars4 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!
Guest favourite
Guesthouse in Jeffersonville
4.94 out of 5 average rating, 35 reviews

Samba Inn - Deck House

Shaniquah & DavidRating, 5 stars5 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!
Guesthouse in Jeffersonville
4.75 out of 5 average rating, 259 reviews

Sweeping Mountain View From Catskills Farm Retreat

AlecRating, 5 stars1 month ago
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.
Guest favourite
Guesthouse in Mongaup Valley
4.99 out of 5 average rating, 400 reviews

Good Vibes Studio in the Woods

GraceRating, 5 stars2 weeks ago
This studio was so sweet and cozy. My partner and I loved the hippie vibes, there were so many cool pieces of decor, lighting options, and colors on the walls and furniture. If you prefer a soulless beige air BnB this is not the place for you. We also loved how many games were available, and there was a great selection of books and DVDs to choose from. The kitchen was well supplied with all the pots pans dishware and utensils you could need, a super nice stove/oven, and fridge. The place felt super homey but also was extremely clean. We loved the views of the woods and felt we had sufficient privacy all weekend. Jen was super responsive and helpful but not overly present. Given that we were there for Valentine's weekend, she even left a gift of some roses for us to enjoy. Honestly I cannot recommend this air BnB enough, it was everything we were hoping for and more. Thank you so much Jen!
Guesthouse in Swan Lake
4.95 out of 5 average rating, 309 reviews

Bamboo House Retreat in Catskill

MillyRating, 5 stars22 months ago
Had a lovely getaway from the city.. very peaceful. Just what I needed

Guesthouses with a patio

Guest favourite
Guesthouse in Hudson
5 out of 5 average rating, 44 reviews

Hudson Countryside Guest Cottage w/Amazing Views

MichaelRating, 5 stars4 months ago
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!
Guest favourite
Guesthouse in Kerhonkson
5 out of 5 average rating, 31 reviews

Cozy Guesthouse & Healing Vibes

DeliaRating, 5 stars1 month ago
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.
Guest favourite
Guesthouse in Callicoon
5 out of 5 average rating, 67 reviews

R52Creekside one bedroom cottage

KevinRating, 5 stars2 weeks ago
The area is awesome, great town. Alot of local spots close to the house. the house was beautiful, the property is really nice. it's private but your also very close to alot. Randy was extremely nice. looking forward to our next trip, we will be back! thank you again Randy!
Guest favourite
Guesthouse in High Falls
4.97 out of 5 average rating, 31 reviews

Modern and warm guesthouse

EstefaniaRating, 5 stars2 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 favourite
Guesthouse in Bloomingburg
5 out of 5 average rating, 15 reviews

Mondrian Manor

LoriRating, 5 stars2 months ago
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.
Guest favourite
Guesthouse in Accord
4.91 out of 5 average rating, 113 reviews

Tiny Horse Barn

GregRating, 5 stars2 weeks ago
The Tiny Horse Barn was a perfect weekend getaway from the city. The space is cozy and private and we felt right at home there. Our hosts were wonderful, changing a propane tank late one night and shoveling out our car when it snowed a few inches. Can’t wait to come back when the weather is better!
Guest favourite
Guesthouse in Margaretville
4.9 out of 5 average rating, 10 reviews

Rosa Guesthouse. - 10 Mins to skiing - private

AshleyRating, 5 stars1 month ago
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!
Guest favourite
Guesthouse in Kerhonkson
4.89 out of 5 average rating, 109 reviews

Cozy Catskills Cottage

DavidRating, 5 stars3 weeks ago
Really great couples stay. Cabin is in the back of the host's yard with the entrance to the cabin facing the woods so it has nice secluded feel. Very quiet. Simple little cabin. Rustic hard wood floors. The window from the sleeping loft has a great view. The pond with their ducks is a really nice touch. Host will provide duck feed if you want to feed them. And duck eggs if available! Great restaurants within 10 minutes by car. Mill& Main in Kerhonksen for a little higher end. Great brunch at The Roost in Stone Ridge. Aroma Thyme in Ellenville 15 min away. Center of Woodstock is 45 minutes away. Richard was great. There was a snow storm expected on our final night into the next day and the property was all clear for check out and got on the road no problem. You can be secluded in the woods and get to a high end dinner in 10 min. Best of both worlds.

Guesthouse rentals with a washer and dryer

Guest favourite
Guesthouse in Kerhonkson
4.98 out of 5 average rating, 60 reviews

Kerhamptons Hideaway in Heart of Hudson Valley

BrianRating, 5 stars2 weeks 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!
Guest favourite
Guesthouse in Accord
5 out of 5 average rating, 20 reviews

Game House in Historic Accord

SusieRating, 5 stars3 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.
Guest favourite
Guesthouse in Gardiner
4.99 out of 5 average rating, 171 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

AmandaRating, 5 stars2 weeks ago
Absolutely amazing AirBnB and host. William's retreat was spectacular. When we first pulled in I thought it was much closer to the house than expected, but you have complete privacy with windows on three sides all facing away from the house. We never saw anyone else and had complete serenity. The hot tub was absolutely amazing, with robes and slippers and a beautiful shower when back inside. The space is extremely comfortable and the bed was the best we've ever slept in in an AirBnB. The house has incredible amenities -- everything you need in the kitchen, blankets on the couch, walking sticks for hikes, a backpack for a picnic, a closet full of replenishments, and a bottle of wine! I honestly cannot wait to stay here again. The view is incredible and we spent a ton of time just standing in the kitchen gazing out at nature. Thank you for a great and relaxing stay!
Guest favourite
Guesthouse in Olive
4.99 out of 5 average rating, 100 reviews

The Lily Cottage Guesthouse

AngelRating, 5 stars1 day ago
An amazing stay! The cottage is such a cozy space and James is an awesome host! The cottage is perfectly spaced between fun tourist spots like Woodstock and New Paltz. The Ashokan Reservoir is a short five minute drive away with an amazing view and nice trails. This wasn’t my first stay at Lily Cottage, and it most certainly won’t be my last!
Guest favourite
Guesthouse in East Meredith
4.98 out of 5 average rating, 129 reviews

Lily Pad by the Ponds

NickRating, 5 stars4 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!
Guest favourite
Guesthouse in Parksville
4.94 out of 5 average rating, 33 reviews

Wonderful getaway place in the Catskills!

JayRating, 5 stars3 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!
Guest favourite
Guesthouse in Stanfordville
4.93 out of 5 average rating, 179 reviews

Eco Cottage in the Woods

SusanRating, 5 stars4 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 favourite
Guesthouse in Red Hook
4.94 out of 5 average rating, 93 reviews

Private Cottage, Walk to Restaurants and Shops

beccaRating, 5 stars1 month 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!

Quick stats about guesthouse rentals in Shandaken

  • Total rentals

    30 properties

  • Nightly prices starting at

    $72 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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