Cottage vacation rentals in Sleepy Hollow

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Popular amenities for Sleepy Hollow cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Greenwood Lake
4.84 out of 5 average rating, 210 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Daphne FiguereroRating, 5 stars2 weeks ago
We booked the house for five nights for a group of six adults and had a lovely visit. Gabriela was a fantastic host communicating super promptly to our questions. It rained 90% of the time so we used the interior of the house to the fullest, and not the exterior (no fire pit, bikes, or hot tub) so cannot comment on those features. All appliances worked well. Kitchen is helpfully labeled and well stocked with kitchenware. The beds were very comfortable, towels fluffy, and downstairs family/game room is a great space for all ages. Furniture was comfortable, dining table was welcoming and though the house shows a bit of wear and tear here and there, everything was clean, tidy, and decorated appealingly. Tip: Bellvale Market just 7” away had great quality food products; Warwick, a quaint larger town, is just 10-15” away providing all other conveniences.
Top guest favorite
Cottage in Greenwood Lake
4.97 out of 5 average rating, 118 reviews

Romantic Experience Secluded Lake House + Hot Tub

KenRating, 5 stars2 weeks ago
What a wonderful experience! I wanted to celebrate my wife’s birthday and this was a fantastic place to do it! We had a terrific time. The house is beautiful and well appointed. Location was great . Visited 2 Farmer’s market and enjoyed the beauty in general. We will return! Thank you for being a gracious host!❤️
Top guest favorite
Cottage in Highland Lakes
4.97 out of 5 average rating, 331 reviews

The Mountaintop Lakehouse that Time Forgot.

JuanRating, 5 stars3 days ago
Surprised my girlfriend with a weekend get away for her birthday and she was thrilled. Evelina and John are great host and their place is warm and welcoming. We loved the lake, and the quiet serenity of the location is perfect for a weekend trip from the city. Also loved the kitchen which made cooking in a breeze because how thoughtfully organized it was. Although our stay was short we did find time to take the canoes out explore the lake and take a refreshing dip. Our only complaint was that our stay wasn’t longer, and we’re both looking forward to coming back !
Guest favorite
Cottage in Wurtsboro
4.88 out of 5 average rating, 26 reviews

Renovated lakeside retreat-hot tub-swingset-fenced

LorinRating, 5 stars3 weeks ago
The house was beautiful and my family loved it. The swingset outside and the toys inside kept my kids occupied and happy the whole time. The house is very kid friendly which was great for us. The house is right by the lake and we were able to go fishing and even use the kayak. We had a very peaceful stay and would definitely come again.
Superhost
Cottage in Kent
4.83 out of 5 average rating, 236 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

KatieRating, 5 stars4 days ago
What a wonderful week we had at Martin’s home! The home was beautiful, very clean, well decorated, and probably the best stocked kitchen of any Airbnb I have ever rented. We were just four minutes from the town of Kent but felt like we were a world away in the woods. This home is off of a lane country road set back a bit with woods behind the house, a beautiful back deck with a dining table and a grill and a hot tub. The bedroom and living area were extremely comfortable for our staycation and we enjoyed cooking all of our meals on the grill. Macedonia State Park as well as the Appalachian Trail are just one or two minutes down the road and we enjoyed taking our dog on hikes there. From start to finish, Martin was extremely communicative with us prior to our arrival and throughout our stay as needed. This place is a gem and if you are looking for a country getaway in a beautiful home, not too far from New York, this is it. We will certainly be back!
Superhost
Cottage in Cold Spring
4.78 out of 5 average rating, 230 reviews

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

EdgarRating, 5 stars1 week ago
Very nice peaceful places and very good service i will definitely be back soon, thank you
Cottage in Kerhonkson
4.81 out of 5 average rating, 183 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

MatthewRating, 5 stars1 month ago
Kyle and Jasmine had a lovely space and was exactly what we were looking for for our trip! Highly recommend booking with them! Their hot tub is amazing as well
Top guest favorite
Cottage in Monticello
4.98 out of 5 average rating, 133 reviews

Dutchhillcottage, gem in the southern Catskills.

JimRating, 5 stars2 weeks ago
Best Airbnb we have stayed in. Beautiful house, amenities, property and so quiet at night you would think you were in the middle of Alaska.

Pet-friendly cottage rentals

Guest favorite
Cottage in Vernon Township
4.94 out of 5 average rating, 193 reviews

Rustic Chic Lake view cottage 50 miles from NYC

DavidRating, 5 stars2 weeks ago
Cozy cabin in peaceful surroundings. Place had everything you need. Communication with host superb - responsive and helpful. Enjoyed our stay.
Guest favorite
Cottage in Gardiner
4.93 out of 5 average rating, 320 reviews

Tiny cottage on DiR mini farm

VictoriaRating, 5 stars2 weeks ago
This was our second visit to this charming cottage and it did not disappoint. Amitai is a wonderful host. He reached out after our check-in to make sure all was well, which it was. The cottage is charming, and the surrounding countryside is gorgeous. Our favorite spot at the cottage is the screened in porch that overlooks a small pond. At night there was a chorus of frogs that was sublime. Minnewaska State Park is a short drive away which we loved! There were a few grass cutters and lawn mowers interrupting the quiet which was unfortunate, but when they stopped the peace and quiet returned, and we were happy.
Guest favorite
Cottage in Greenwood Lake
4.93 out of 5 average rating, 189 reviews

Cozy home in the Village of Greenwood Lake

MichelineRating, 5 stars2 weeks ago
I love the fresh air flowing throughout this entire little cottage. Every room invites dappled sunlight filtered through lush summer foliage. It is truly cozy, whether enjoying a coffee on the back porch, journaling at the desk or chilling on the big comfy couch. Walk out the door and the lake and charming downtown are steps away. I find myself thinking I could truly spend a happy month, here. Stay. Return. I know I will.
Superhost
Cottage in Carmel Hamlet
4.83 out of 5 average rating, 162 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

ErinRating, 5 stars1 week ago
This place was wonderful. We were only there for a quick stay, and it was rainy, but that was ok because the cabin was so cute and cozy and fun. A bit of time sitting in the chairs out front in the morning with my coffee was exactly the quick weekend rejuvenation I needed. The cabin had everything we needed (and plenty of things we didn't need on this trip, but you might! I could see us playing board games or relaxing out on the back patio on a future trip.) A previous reviewer said this spot is what you expect an Airbnb to be, and that's exactly right. We picked it at first because it was convenient to a few Westchester things we needed to do, but we didn't want to drive home afterwards to CT on a summer Friday night. Spending this little bit of time in the Carmel area was genius because now we can't wait to go back there specifically for a real visit!
Guest favorite
Cottage in Pine Bush
4.89 out of 5 average rating, 272 reviews

Seclusion and Romance - Pool is open and heated!

KarenRating, 5 stars2 days ago
Although there is a lot to do within a short distance (hiking, bars, etc..), I chose this place specifically for the fenced in pool area. Coming from a NYC apartment with a dog and no outdoor space, this was exactly what I was looking for and better than expected. My dog was able to roam freely the entire day while we relaxed and lounged out by the pool or sat on the patio furniture by the fireplace that was completely covered and shaded. Richard's place did not disappoint!
Guest favorite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 356 reviews

Be in Nature at this Gorgeous Riverfront Cabin

AaryaRating, 5 stars1 week ago
We loved the place, it was a beautiful home with lots of light and accessible green space. It was perfect for a short getaway. It’s a short drive from nearby towns and was very easy to find based on the directions. Mark was a responsive and accommodating host and we had a wonderful time in his airbnb.
Guest favorite
Cottage in Newtown
4.93 out of 5 average rating, 256 reviews

Private and Serene home close to I-84 and shopping

LauraRating, 5 stars1 week ago
Very communicative and perfect description of what was expected.
Guest favorite
Cottage in Kerhonkson
4.95 out of 5 average rating, 148 reviews

Catskills Country Cottage

JenRating, 5 stars2 weeks ago
My mother and I recently stayed at Consuelo's cottage. We stayed here a few times before. Everything is easy about the check in/check out process. Her house is spotless and comfortable. Beautifully decorated with everything you could need in the kitchen, bathroom and living room, etc. and free of extraneous clutter, so you can really make yourself at home and feel like it's "yours" for the time you are there. Beds are very comfy and bedding was superb. There are nice mini-splits in the bedrooms and other rooms, so you can adjust the temperature as needed, and there are plenty of sitting areas, tables and chairs as well as a nice big island in the kitchen for hanging out around. We loved sitting on the nice deck out back and watching birds and bunny rabbits in the back yard! Of course the location is super easy for hiking at Minnewaska and the surrounding areas. All in all- definitely worth your time and money- highly recommend! Also, Consuelo is lovely, helpful and accommodating.

Private cottage rentals

Superhost
Cottage in Putnam Valley
4.94 out of 5 average rating, 68 reviews

Getaway On Grove – Cozy Cabin by the Lake

EloiseRating, 5 stars3 weeks ago
A stylish, cosy and well-proportioned property perched in the trees in a beautifully landscaped yard with a stream. Felt private and serene. Steps from the children’s beach at the lake and an easy walk to nearby hiking trails. Very easy access off the Taconic. A true retreat. A perfect spot to turn your phone off for a couple of days.
Guest favorite
Cottage in New Fairfield
4.97 out of 5 average rating, 38 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

RyanRating, 5 stars1 week ago
Great place to stay - easy instructions to follow, house is even more spacious than it looks in photos, and the backyard is GREAT for dogs. Would definitely recommend.
Guest favorite
Cottage in Putnam Valley
4.94 out of 5 average rating, 87 reviews

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

AlexRating, 5 stars1 day ago
My family and I had an incredible time in this beautiful house, everything in order and I loved every space of this house, very happy we will be back
Top guest favorite
Cottage in Katonah
4.94 out of 5 average rating, 62 reviews

Cozy Northern Westchester Artist/Writers Cottage

RobertRating, 5 stars3 weeks ago
We stayed in Marks’s Writer’s Cottage for five nights when visiting friends in Westchester. We recommend it without reservation. The location in Katonah is wonderful. We enjoyed taking walks through the neighborhood in the mornings and checking out all the interesting Victorian houses. We also appreciated being able to eat at the local restaurants (Blue Dolphin ) and cafes (LMNOP) in walking distance. Multiple markets are also a walk away. It was also a great base for visiting Northern Westchester where there aren’t many options for longer stays. We’d been planning to stay in hotels near Tarrytown before finding Mark’s place; being in Katonah made our trip much more special. The house was great. It definitely feels like a cottage out in the woods even with the main house across the backyard. We enjoyed the privacy and space after a long urban trip, appreciated the well-stocked kitchen, and writing and sitting space. We might have appreciated a sofa downstairs for lounging.
Guest favorite
Cottage in Newburgh
4.97 out of 5 average rating, 61 reviews

Lakefront Getaway 1 Hr from NYC

Zeke & KrisRating, 5 stars1 month ago
I stayed for a month solo to focus on my projects & it was the most peaceful month. The house is contained in nature with a plethora of birds & animal life that I witnessed.. a crane fishing at the creek beside the house as I worked, a pair of woodpeckers hunting at the lawn, a chipmunk that lives under the house & has a morning ritual of its own. All while the lake boasted breathtaking sunsets. On the practical side, the kitchen was fully equipped with everything one needs to cook everyday, which I did. It was private & safe for a solo girl like me to stay a month. Amazon found its way to it no problem. And there are nice streets to take long walks which I did 1 hour a day. Very friendly neighbors, everyone waves at ya. The covered patio, working from the dinner table, waking up in the bedroom to the lake.. all main areas are flanked by beauty. Really was perfect for a solo getaway. Also wifi was very reliable. Keep in mind lake living = insects. They’re harmless. Highly rec renting!
Guest favorite
Cottage in Putnam Valley
4.96 out of 5 average rating, 25 reviews

3 Br Cottage near Lake w Private Dock, 1 hr to NYC

CarolynRating, 5 stars7 months ago
The cottage was inviting and enabled family time around the fireplace. The kitchen was well equipped with everything in good working condition. The master bedroom was warm and comfortable. The bathroom suitable. The walk down to the lake, as described in the listing, was a favorite. Watching the sunset over the water was memorable and gave a nice photo op.
Top guest favorite
Cottage in West Milford
5 out of 5 average rating, 38 reviews

Happy Day Chalet, a lakefront stay to relax & play

RyanRating, 5 stars2 weeks ago
Stay was perfect, it’s shows the at the owner cares about the guest experience! Perfect spot right on the lake and freshly renovated.
Top guest favorite
Cottage in Warwick
5 out of 5 average rating, 60 reviews

Ranch in the Woods | A Peaceful Designer Retreat

KarismaRating, 5 stars1 week ago
Super peaceful and very clean. Would 100% stay again

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