Cottage vacation rentals in Sleepy Hollow

This home was everything we hoped it would be. It offered a peaceful location for our family (two kids, 4 and 2). The home was cozy and the recommendations from Nadia were great. We went to several of the recommended restaurants as well as the Teddy Bear museum and hiked the Rosendale Trestle. Truly a wonderful stay.

The place was clean, beautifully kept and well supplied- we loved the backyard! Gabriela was very communicative. Highly recommend!

The place smells amazing and the bedding is so soft and delicious. Perfect place to get away and be in nature.

Our stay at Martin's place was fantastic! The property is quaint, cute and conveniently located to downtown Lichfield and surrounding nature centers and trails. A highlight for the trip was White Memorial Foundation, tons of trails along beautiful ponds, marshes and grassy hills. Martin provided amazing directions for the house and was super responsive and proactive when needs arose. I would highly recommend Martin's property to any family or group of friends looking for a relaxing and adventurous time in Northern Connecticut!

Rene was very responsive and gave very clear instructions on things. Place was very neatly put together and the area is very beautiful for a getaway.

Evalina and John were the best hosts we’ve ever had! There was a big winter storm during our trip and the power in the area went out briefly and John was over at our place turning on the generator right away. Highly recommend staying here

Just as described- a peaceful and quiet getaway. We’re still talking about it 2 weeks later!

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.

Joshua’s place was clean and spacious. Very peaceful and we loved the little farm with the animals. Wish more businesses like restaurants and parks were opened in the area, but the house itself was great.

Alex was a very gracious host. We had an easy check in and a great first night — the listing was as described and the location was very quiet and scenic. When a big snow storm hit and we had to leave early, Alex was quick to accommodate our early check out. Thank you for being a great host!

What a restful beautiful setting. Beautiful views. We really enjoyed watching the hens roam the yard. A super clean space, roomy and comfortable. Some cute towns nearby like Millerton, Hillsdale, Copake, New Preston, Millbrook. Kent Falls close too.

The host was very pleased understanding and easy to communicate with regarding the entire process. The house is the guest house for the establishment and is adorable. It is perfect for a small group weekend outing. The decorations and esthetics of the house are perfectly arranged to enhance the experience. The beds and linens are very comfortable, and both bedrooms are spacious and lovely. The host made checkout a breeze. We will definitely stay there again when we are in the area! :)

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!

I had an absolutely fantastic stay at Judy and Eric’s cottage! The space was cozy, spotless, and had everything I needed for a comfortable getaway. But what truly made this experience special was their incredible hospitality. A snowstorm hit during my stay, and Judy and Eric went above and beyond by allowing me to stay extra time to ensure I was safe. Their kindness and generosity truly made a difference, and I couldn’t be more grateful. The cottage itself is peaceful and charming, with a breathtaking view into the woods that made for the perfect escape. Waking up to that scenery was one of the highlights of my stay! I highly recommend this place to anyone looking for a relaxing and welcoming retreat. Thank you, Judy and Eric—I will definitely be back!

Darla’s cottage was such a sweet spot for a weekend getaway. Super cozy, clean, and peaceful—exactly what we were looking for. It felt tucked away in the woods but still really easy to get to, and just a few minutes down the road from Rough Cut Brewing, which was a big plus. We loved being able to grab some beers, then come back and relax inside. Darla was a great host—friendly, but gave us plenty of space. Would totally stay again next time we’re in the area!

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.

I have only great things to say about Caitlynn and Matt’s guest house. My travel partner and I were very very very comfortable here. We are both from big cities so I admit it was a little jarring at first to come home to such darkness and quiet but after settling in we just found it cozy and peaceful and like a true retreat. There was some highway noise and lights that shine through the window also there is no microwave but we made do with the ample kitchen supplies and the airfryer which was very multifunctional. The highlight for me was the bed, soft sheets and it was a perfect memory mattress. They keep the cottage super clean, and that’s coming from a stickler! Caitlynn was also so helpful and responsive and her guidebook recs was what drew us to choosing their place. 100% recommend for any couple or solo traveler who wants a beautiful, tidy and quaint home base with easy driving access to all the Hudson Valley has to offer. We miss Caitlynn and Matt’s place already, thanks guys!

Had such a beautiful time at the lake cottage! Was perfect inside and out. All of our experiences together were amazing and I loved the way the lake was right in our view from the house. Jenna really ensured that all of the amenities that someone would need were there for use. Definitely worth the trip and would recommend to anyone that wants a private little getaway! Fireplace was a great feature as well. Amazing and affordable! Super clean and comfy.

This charming cottage in Upstate NY is the perfect escape from city life. Surrounded by towering trees and nature’s tranquility, it offers a cozy, welcoming retreat. Inside, the rustic decor, soft lighting, and warm bed create the ultimate cozy atmosphere. The well-equipped kitchen and plush bed ensure comfort, making it easy to relax. The outdoor space is a highlight—sip coffee on the porch, stargaze , or explore nearby hiking trails. Whether you’re a couple, solo traveler, or small family, this peaceful retreat is a must-visit. Highly recommended!

Well thought out space. Quiet neighborhood. Has all the essentials needed for vacation. There is a chair in the bedroom that converts into a small single bed for a child. Nice backyard space.

Easy stay, great communication, accommodating and a lovely place!

My husband and I stayed at the cottage for 3 months and enjoyed our time very much. We were very happy from every perspective: The cottage had all the equipment we needed and wished for. We sometimes used the fireplace and loved the bed/couch. The cottage is perfect to rest and focus. We enjoyed to have so much nature around us. We took a walk in the close park with a lake almost every day. We liked to live at a small farm with dogs, chicken and goose. Debbie and Kirk were always there when we needed them and also made us internationals feel welcome. They explained and helped us proactively e.g. changed regional weather circumstances. We also regularly got eggs from the chicken what was always a nice surprise. Communication/ interactions were always easy and friendly. I recommended my work to plan future stays for assignments in this Airbnb. In our opinion it is better than a hotel: Very comfortable, cozy, close to nature and a special American experience. Thanks a lot Debbie and Kirk

we love Walkers place and do come here twice a year. it's a beautiful home, it's so zen, so pretty, so clean, we just absolutely love it. it's a great fabulous house and spot to stay. ♥️

T’s house perfectly matches my expectations, his hospitality and responsiveness went beyond satisfaction, everything inside the house is clean and full of details, the view and surroundings the house is breathtaking. We enjoyed very much for our stay. This house now has a special meaning for us, we will definitely come back! For anyone interested: T is one of the best hosts I’ve met, you will be amazed and impressed.