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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, 206 reviews

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

CheyenneRating, 5 starstoday
Beautiful home! I loved the stay very peaceful, definitely will be returning soon and the host was very lovely.
Guest favorite
Cottage in Greenwood Lake
4.97 out of 5 average rating, 114 reviews

Romantic Experience Secluded Lake House + Hot Tub

TaylorRating, 5 stars4 days ago
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!
Top guest favorite
Cottage in Highland Lakes
4.97 out of 5 average rating, 322 reviews

The Mountaintop Lakehouse that Time Forgot.

NathanRating, 5 stars5 days ago
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!
Guest favorite
Cottage in Wurtsboro
4.91 out of 5 average rating, 23 reviews

Renovated lakeside retreat-hot tub-swingset-fenced

MelanieRating, 5 stars5 months ago
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!
Superhost
Cottage in Kent
4.84 out of 5 average rating, 229 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

LeonardoRating, 5 stars5 days ago
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!
Superhost
Cottage in Cold Spring
4.79 out of 5 average rating, 219 reviews

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

AlexanderRating, 5 stars1 week ago
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.
Cottage in Kerhonkson
4.81 out of 5 average rating, 179 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

Ivet CesarinaRating, 5 stars2 weeks ago
An amazing place to visit. It is a very nice place to be.
Guest favorite
Cottage in Patterson
4.9 out of 5 average rating, 49 reviews

The Silent Sun Cottage Hottub/Kayak/Firepit/BBQ

CallaRating, 5 stars1 month ago
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

Guest favorite
Cottage in Woodridge
4.85 out of 5 average rating, 121 reviews

Outlier Inn Cottage on Farm Upstate Catskills

LindseyRating, 5 stars2 weeks ago
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!
Top guest favorite
Cottage in Cornwall
5 out of 5 average rating, 52 reviews

Carriage House: Romantic Hideaway near West Point

LeAnnRating, 5 stars1 week ago
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!!
Top guest favorite
Cottage in Putnam Valley
4.94 out of 5 average rating, 82 reviews

Charming Cottage Retreat | Grill & Steps to Lake

Jo AnnRating, 5 stars3 weeks ago
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!
Guest favorite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 347 reviews

Be in Nature at this Gorgeous Riverfront Cabin

MichelleRating, 5 stars1 week ago
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
Guest favorite
Cottage in Pine Bush
4.89 out of 5 average rating, 264 reviews

Seclusion and Romance - Hot Tub is hot hot hot

KemoneRating, 5 stars2 months ago
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!
Guest favorite
Cottage in Newtown
4.93 out of 5 average rating, 243 reviews

Private and Serene home close to I-84 and shopping

TonyRating, 5 stars1 week ago
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.
Guest favorite
Cottage in Wurtsboro
4.91 out of 5 average rating, 32 reviews

Cute Upstate Cottage - 90 Minutes from NYC!

KimberlyRating, 5 stars2 weeks ago
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!
Top guest favorite
Cottage in Redding
4.93 out of 5 average rating, 259 reviews

Cozy Cottage by the pond

MaryEllenRating, 5 stars2 weeks ago
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

Superhost
Cottage in Pine Bush
4.95 out of 5 average rating, 86 reviews

Modern BoHo 3BR Cottage Near by Hiking, Winery

KateRating, 5 stars1 month ago
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!
Superhost
Cottage in Mohegan Lake
4.92 out of 5 average rating, 202 reviews

The Pearl of Westchester

CesarRating, 5 stars2 weeks ago
Great place for a family getaway
Superhost
Cottage in Cold Spring
4.96 out of 5 average rating, 23 reviews

Romantic Private Lake Art-Deco Cabin Hudson Valley

JamesRating, 5 stars10 months ago
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.
Guest favorite
Cottage in Pawling
4.97 out of 5 average rating, 97 reviews

Forest Acres Cottage: Art East is soon! May 3 - 4

Bill McGoughRating, 5 stars1 week ago
Great place to stay when in the area. It’s become our ‘go to’ stay!!
Guest favorite
Cottage in Norwalk
4.94 out of 5 average rating, 68 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars2 weeks ago
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!
Superhost
Cottage in Cornwall
4.85 out of 5 average rating, 41 reviews

Cozy Cottage near Hiking and Storm King

AlexandraRating, 5 stars5 months ago
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!
Top guest favorite
Cottage in New Paltz
5 out of 5 average rating, 46 reviews

Peaceful, Serene Country House with Outdoor Pool.

BethRating, 5 stars6 months ago
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!
Guest favorite
Cottage in Englewood
4.88 out of 5 average rating, 77 reviews

Cambridge Cottage - Your own "Private Oasis"

JackRating, 5 stars6 days ago
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!

Destinations to explore