
Cottage vacation rentals in Sleepy Hollow
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Top-rated cottage rentals in Sleepy Hollow
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Popular amenities for Sleepy Hollow cottage rentals
Cottage rentals with a hot tub

Cozy Cottage | HotTub & Family Rm | 1H fr NYC
Beautiful home! I loved the stay very peaceful, definitely will be returning soon and the host was very lovely.

Romantic Experience Secluded Lake House + Hot Tub
Chateau René is the perfect peaceful escape. The home cozy and well maintained - exactly as pictured. The view made every morning feel like a dream. René was so warm, responsive, and accommodating. He shared great local recommendations and clear instructions for the house, which made settling in a breeze. The most special part of my stay was getting engaged here! René secretly coordinated with my now-fiancé and friend to make it all happen. His excitement and willingness to help meant a lot to us. Overall, 10/10 stay. We’ll definitely be back!

The Mountaintop Lakehouse that Time Forgot.
A hidden gem! This spot has a ton of character and the hosts are awesome! The lake and surrounding area is beautiful as well, with plenty to do for the outdoorsy type and cute shops and great restaurants within minutes. would highly recommend and hope to find time for a return trip!

Renovated lakeside retreat-hot tub-swingset-fenced
We had the perfect stay for our Thanksgiving. Lots of toys for the kiddo, backyard for the dogs to run around, and a well-stocked kitchen for all our cooking needs (utensils, platters, etc). Sadly we didn’t get to use the play set or the fire pit due to the weather, but we hope to come back when weather is slightly warmer!

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl
Second stay at Martin’s place and it was even more pleasant that the first. The house was very organized when we arrived, and the clean decor makes the environment peaceful and relaxing. It’s right off the road, but not noisy, which makes it convenient to go to Kent town center. We’ll be going back!

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard
The house is well maintained and clean. The kitchen was well stocked with everything needed to cook/grill. The hot tub was pleasant and the backyard was great for our kids. The location is only about 7 minutes from downtown Cold Spring and 15-20 minutes from Beacon. The location was ideal for wanting a mix of peace and quiet with accessibility to local attractions.

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park
An amazing place to visit. It is a very nice place to be.

The Silent Sun Cottage Hottub/Kayak/Firepit/BBQ
This is the second time we stayed here and it was even better than the first! They have really taken the time to make the place as welcoming and easy to navigate as possible.
Pet-friendly cottage rentals

Outlier Inn Cottage on Farm Upstate Catskills
We enjoyed the lovely cozy, private cottage with our family. It was a pleasure to have the animals nearby for the kids to interact with, a safe environment to roam in the woods, and very convenient to have the farm shop a few steps away for local eggs, meats, etc. The cottage was stylishly modern with a clean aesthetic and modern conveniences. Josh was very accessible via text/phone and checked in with us during our stay. We enjoyed ourselves thoroughly and would recommend to nature lovers, families, and those looking for a getaway in the woods!

Carriage House: Romantic Hideaway near West Point
The adorable carriage house was just perfect for my husband and me and our dog! We were in town for a wedding, a visit with our son, and a retirement ceremony, so we stayed for over a week. The house was cute, clean, spacious, and located in the lovely town of Cornwall. We went for walks in the morning through the town, worked from the house during the day, and went out in the evening into neighboring towns. It was very close to Beacon and West Point where some of our activities were. Catherine and Jay were wonderful hosts and we would love to stay here again and also venture out to one of their other properties that they host!!

Charming Cottage Retreat | Grill & Steps to Lake
Tech savvy home. All the right plugs for our electronics. Heated bathroom floor a plus during cold weather. Upstairs bedroom had hanging space and dresser, but neither available in lower bedroom. Did have luggage rack in lower bedroom. Definitely a do again for me!

Be in Nature at this Gorgeous Riverfront Cabin
Second time staying at Mark’s place and doesn’t disappoint! Quiet serene natural setting with all the convenient amenities of a home away from home

Seclusion and Romance - Hot Tub is hot hot hot
Nice little getaway during the cold season. The hot tub was excellent and about 100 degrees so perfect even with the cold temperature. It was still possible to put together a meal with the propane grill and warm things up in the microwave or store them away in the fridge. The heat was excellent in the space. Seems like it would be a great place to stay in the summer as well!

Private and Serene home close to I-84 and shopping
We were looking for a last minute peaceful four day getaway and we found it here. We can’t stop talking about it. Although relatively close to everything we felt as if we were in the middle of a forest. The only sounds were the chirping of song birds and a woodpecker in the morning. Local restaurants are great and for us a trip to Yale University’s free museums and nearby antique shops rounded things out. The house is charming and Rio, our host , made sure we had everything. The few things we forgot from home were there! Wonderful experience all around.

Cute Upstate Cottage - 90 Minutes from NYC!
I had a great stay! The Airbnb met all my expectations—it was clean, comfortable, and very cozy. The space had everything I needed, and the atmosphere made it easy to relax. The owners were also super responsive and helpful with all my questions, which made the whole experience even better. I’d definitely stay here again!

Cozy Cottage by the pond
My husband and I had a great stay. James and Rose are super helpful hosts. It’s a great place to relax and enjoy nature. Walking distance to a lovely park they recommended with tons of hiking trails and very quiet.
Private cottage rentals

Modern BoHo 3BR Cottage Near by Hiking, Winery
Had a wonderful stay at The Green House. Home was exactly as pictured and very clean. Ada and Miranda were wonderful, responsive hosts and we loved the proximity to various hiking trails. The kitchen was stocked with all of the dishes and utensils to make your meals. Truly a peaceful oasis!

The Pearl of Westchester
Great place for a family getaway

Romantic Private Lake Art-Deco Cabin Hudson Valley
The area was absolutely beautiful. Valhalla Lake was private with stunning views. The cabin was exactly as it was described and the book of directions that was left for guidance was easy to follow.

Forest Acres Cottage: Art East is soon! May 3 - 4
Great place to stay when in the area. It’s become our ‘go to’ stay!!

Seaside Serenity: 2B 1B, Patio,Near Beach
We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!

Cozy Cottage near Hiking and Storm King
Such a cozy cabin! Super friendly host(s) who are responsive and were able to answer any question. Would stay there again and plan to! 5 stars for a peaceful quiet weekend!

Peaceful, Serene Country House with Outdoor Pool.
Our stay at Laurel and Ash's cottage tucked into the woods was incredible. It is even more beautiful than the photos! The house is beautifully decorated and was spotless when we arrived. The design is thoughtful and the furniture and beds are comfortable. It is the most well-appointed Air BnB we have ever stayed at! We had absolutely everything we needed... toiletries, cleaning items and towels for the kitchen, cooking spices and oils, soft and cozy throw blankets, bluetooth speaker, cell phone charger, yoga mat and weights! The pool area is gorgeous and was awesome for morning coffee, we were there in the fall and the pool was closed. Location is just a few minutes from downtown New Paltz. We can't wait to come back!

Cambridge Cottage - Your own "Private Oasis"
Chrystal was super responsive to all our questions and needs, and gave us a warm welcome when we checked in on our first day. The lovely cottage was fully furnished and had everything our small family needed. The neighborhood was quiet, safe, and perfect for walks. Getting to downtown NYC across the G.W. Bridge only took about 20-30 minutes, very convenient. We made wonderful memories during our 9-day stay!
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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Jones Beach
- Barclays Center
- Tenement Museum
- Fairfield Beach
- Riverside Park
- Rye Beach
- Comedy Cellar
- Mountain Creek Resort
- Apollo Theater
- Gilgo Beach
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- Rye Playland Beach
- MetLife Stadium
- Inwood Hill Park
- United Nations Headquarters
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