Family-friendly holiday rentals in Ashokan Reservoir

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Popular amenities for Ashokan Reservoir family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Mount Tremper
4.9 out of 5 average rating, 227 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Barbara And JeremyRating, 5 stars1 day ago
very comfortable accommodations and a great place to spread out if you want a bit of privacy. three of us stayed there comfortably
Guest favourite
Home in Bearsville
4.92 out of 5 average rating, 232 reviews

A Cozy’s Woodstock Getaway Home

BradfordRating, 5 stars1 month ago
We had a great stay at BorisRungcheewan’s place. Check-in was easy, and the hosts sent us all the necessary information well in advance. The only minor challenge was finding the house—it’s set back from the road and located at the top of a long, steep driveway. I can imagine that arriving for the first time in the dark could be a bit tricky. The house itself was just as advertised: very private and quiet. The interior was comfortably furnished, and we especially appreciated the fireplace and the Bluetooth speaker. The two full bathrooms were also nice . The hot tub was easy to use, although a few of the jets didn’t seem to be working. The kitchen was well-stocked with pots, pans, plates, and glasses. The house is about 15 minutes from the Woodstock area and the nearest grocery store, so we’d recommend stopping to pick up any necessary provisions before checking in. Overall, we would absolutely return to BorisRungcheewan’s place for another stay.
Top guest favourite
Flat in New Paltz
4.97 out of 5 average rating, 545 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

StephenRating, 5 stars2 weeks ago
Such a perfect location for a weekend in new paltz and the views from the patio/hot tub are absolutely spectacular. Ami was a great host!
Superhost
Home in Olivebridge
4.92 out of 5 average rating, 458 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

AmeliaRating, 5 stars1 month ago
We had a wonderful time at this place for our mini moon. It was relaxing, beautifully decorated, well stocked with everything you need! The hosts were very responsive. We would stay here again in a heartbeat! For anyone coming from NYC we stoped at Pho Tibet in New Paltz for lunch on the way home and the food was amazing!
Guest favourite
Home in High Falls
4.95 out of 5 average rating, 219 reviews

Clove Schoolhouse on Mohonk Preserve

PaulRating, 5 stars1 week ago
We had a nice time staying. It has a Well stocked kitchen. It is near to grocery and shopping in Stone Ridge. It has Great fireflies at night and a good view of the sunset.
Guest favourite
Home in Woodstock
4.97 out of 5 average rating, 296 reviews

Romantic Cottage -Amazing Views -Spa -Woodstock NY

RobinRating, 5 stars4 weeks ago
Dror’s place was the ideal getaway. It was just the right size for one or two people. It was clean, cozy, and had all the right amenities, including coffee makers, coffee, and even a frother! Unfortunately, it rained all weekend, so I couldn’t enjoy the hot tub. But the space in the backyard was very peaceful and inviting. I left you a drawing, Dror, and wanted you to know that I haven’t drawn in many years because of a busy life. Your home brought that out in me. Thanks again!
Guest favourite
Cabin in Wurtsboro
4.93 out of 5 average rating, 101 reviews

Catskills cabin over waterfall w/ views & hot tub

Ana PaulaRating, 5 stars4 weeks ago
It is clear Adam and Chrissy take care of this place like their own home. I cannot emphasize enough how wonderful this place is. Perfectly equipped, yet doesn’t feel cluttered. Cozy, tasteful, full of wonderful little details, clear instructions and good vibes overall. Location is amazing and perfect for days of reflection / retreat in the mountains. Has all you need in the kitchen, plenty of books, board games, movies, records, even Atari and an AMAZING outdoor spa. Best of all is the water stream running below: natural forest + running water sounds - not even headspace can give you this to perfection. Outdoor seating area also lovely. I felt at home from beginning to end. Hosts incredibly responsive and helpful. Can’t wait to return !
Superhost
Home in Woodstock
4.93 out of 5 average rating, 930 reviews

1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole

GabrielleRating, 5 stars4 weeks ago
Jonathan’s place was fantastic! Location felt like a secluded oasis, but was only 5 mins to town. Everything was clean, hot tub and sauna included. Our pups greatly appreciated running around in the fenced in yard. Jonathan was quick to respond the one time we messaged. Would absolutely stay there again!

Family- and pet-friendly home rentals

Top guest favourite
Home in Accord
4.97 out of 5 average rating, 137 reviews

The Woods House, 40 secluded acres & speedy wifi!

DanRating, 5 stars4 weeks ago
Donna's place was amazing! We knew we would love it from the pictures but were even more blown away when we walked inside. It was the perfect cabin with every amenity and more that you could want for a remote get away in the Catskills. We went up with our dog and loved every minute - will definitely go back for our next trip up!
Top guest favourite
Tiny home in Shandaken
4.87 out of 5 average rating, 190 reviews

Cute Cabin with Great Mountain Views

ChrisRating, 5 stars1 day ago
We had the best time staying at this cozy cottage, very comfortable with an awesome view! Kitchen had everything we would need. Great hospitality from Wayne and Renee! We can’t wait to come back again soon
Guest favourite
Cabin in Big Indian
4.96 out of 5 average rating, 271 reviews

Retro Modern Paradise in the Catskills

AlecRating, 5 stars3 weeks ago
Would absolutely stay again! Really loved the way they've updated the space but kept the classic touches of the house. Huge well appointed kitchen with everything you could need. Peaceful outdoor space with lots of privacy. And overall a very spacious house that feels like you could have a big group without getting in each others way. Ryan & Lauren were super on it. Will definitely recommend to friends.
Guest favourite
Cottage in Woodstock
4.84 out of 5 average rating, 255 reviews

Woodstock Dog friendly Cottage in Town; large yard

EvanRating, 5 stars2 weeks ago
Right in the heart of Woodstock, walkable to town. And on top of all that, my dogs were as comfortable as they could be away from home. Anne was responsive and kind, the smokeless fire pit was amazing, the bed was ultra comfortable. Air purifiers are abundant, place always felt clean. The balcony on the second floor overlooking the mountain was an added bonus. Wouldn’t have a complaint if I tried.
Top guest favourite
Home in New Paltz
4.97 out of 5 average rating, 753 reviews

Victorian Haven

JanetRating, 5 stars1 day ago
We have stayed at Erik's place 4 or 5 times now. It's perfect, has everything you need. It is centrally located to surrounding towns. Erik and his parents are very friendly and always responsive. I highly recommend staying there!
Guest favourite
Home in East Durham
4.93 out of 5 average rating, 248 reviews

Bluff House

ChuckRating, 5 stars4 weeks ago
We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!
Guest favourite
Cabin in Woodstock
4.9 out of 5 average rating, 585 reviews

The Pike Lane Cabin & Nature Preserve

ArianaRating, 5 stars2 weeks ago
We've been visiting Darin's place for years and always find it so peaceful and lovely! The hosts are amazing, the land is beautiful, and the cabin is cozy, close to town and our favorite hikes. Can't wait to be back again soon!
Top guest favourite
Cabin in Woodstock
4.95 out of 5 average rating, 177 reviews

Charming Artist Cottage

AminaRating, 5 stars4 months ago
This was our second time staying at Jon’s lovely cabin. We love being in the woods, strolling by the stream and enjoying the fireplace ambiance. Wonderful place with lots of character. We hope to make this a yearly trip.

Family-friendly home rentals with a pool

Superhost
Home in Woodstock
4.88 out of 5 average rating, 167 reviews

Shula | Farmhouse | Pool, Fire pit, Hot tub

MimiRating, 5 stars3 weeks ago
Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!
Guest favourite
Home in Stormville
4.94 out of 5 average rating, 183 reviews

Private Hudson Valley Country Retreat

ElodieRating, 5 stars1 week ago
We were absolutely charmed by this stunning house, surrounded by breathtaking nature and offering incredible views—especially over the lake. Every corner is filled with character and warmth, making it feel like a true hidden gem. A huge thank-you to our wonderful host Sandy, who was incredibly thoughtful and proactive throughout our stay. We couldn’t have asked for a better experience. We’ll be back without a doubt!
Top guest favourite
Home in New Paltz
4.98 out of 5 average rating, 490 reviews

midcentury mod * POOL * walk out trail to mohonk

ArielRating, 5 stars2 weeks ago
This is a lovely house very close to New Paltz. We had a nice long weekend with the kids and loved spending time in the pool. Susan was a great host. No complaints!
Top guest favourite
Home in Saugerties
4.94 out of 5 average rating, 131 reviews

Bluestone Escape - Where everyone is at home.

LoriRating, 5 stars1 month ago
Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!
Guest favourite
Guest suite in New Paltz
4.96 out of 5 average rating, 346 reviews

Majestic Studio with Shawangunk Mountain Views

MariaRating, 5 stars1 month ago
Loved this little studio! If you’re doing anything at Mohonk preserve (we did Rock the Ridge), it’s minutes away from Testimonial Gateway and Ulster County Fairground. New Paltz is just down the road with stores, cafes, and more. The apartment is cozy but functional and the kitchen is setup well. Perfect for 2 people, couple or friends. Bonus — I rented an EV and was stressing about getting it charged but Franky offered to let me charge it overnight, which was a life saver!
Guest favourite
Cabin in Livingston Manor
4.97 out of 5 average rating, 307 reviews

Experience The Zen House

BethRating, 5 stars1 week ago
We had such a great stay at Eugene’s place! The house was perfect for our group — spacious, comfortable, and full of fun things to do. We especially loved the private theatre, the hot tub, and especially the sauna — such a great touch! The volleyball net was a hit, and there were tons of games in the closet that kept us entertained. The kitchen was well-stocked and roomy enough for us to cook meals for our large group, and there were plenty of different areas to hang out in, everyone could find their own space to relax. The towels were plentiful (huge plus) and having access to the washer and dryer came in handy during our stay. Eugene was a fantastic host — super friendly, very responsive, and just really helpful all around. We also got to enjoy a few deer sightings right in the yard, which felt magical. We visited the nearby alpaca farm and did the Beer Mountain hike, which was a nice outing. All in all, a wonderful stay. Would absolutely come back. Thank you Eugene!
Top guest favourite
Cabin in Red Hook
4.96 out of 5 average rating, 353 reviews

Modern Upstate Cabin, near Rhinebeck NY

JenniferRating, 5 stars2 weeks ago
Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.
Guest favourite
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars4 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

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