Pet-friendly holiday rentals in Sleepy Hollow

Beautiful location, peaceful and private. Spacious, modern, comfortable home. Really good advice about places to explore and visit in the surrounding area. This is a place we’d return to in a heartbeat. Just the tonic after a week in Paris and a hectic entry via JFK. Ben’s place is a haven away from the world. We just loved it!

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!

We absolutely loved our stay ay Susan's place. We were celebrating our ten year wedding anniversary with our dogs and it could not have been more perfect! The private pool setting, access to the rail trail that leads directly into town, the giant windows bringing the outdoor greenery inside, the Frida Calla 500 piece puzzle, the I pad hooked up to a lovely sound system, I could go on and on. We rarely visit the same place twice, but we made need to break that streak with this place.

Even better than the pictures! This was one of our favorite Airbnb experiences, super cute and eclectic house. We loved the style, the bathrooms made me want to renovate my own, and the beds were too comfortable if that’s possible lol. Perfect for vacation. The house was centrally located to the airport and the Bible museums and printery we booked to tour. Overall, we had just a lovely stay and cannot wait to go back!

This place is truly a gem! We enjoyed swimming in the waterfalls and relaxing under the trees. We can’t wait to return. The house is also lovely with lots of interesting and quirky touches that we enjoyed. Incredibly well stocked kitchen and everything we could want!

Fantastic spot with views of the lake from the deck. Easy to walk down to the beach and had fun with the kayaks. Lots of space for the kids to run around and play on the open plan kitchen/lounge. Quick drive into town for great shops and places to eat. A lovely community by the lake.

Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!

We had a great stay at Maritza's place in Stamford. It was the perfect distance to the wedding venue that we were visiting for. The place was the perfect size for our group and it was very clean. It was a very hot weekend and there was air conditioning in every room, which was nice. Maritza was responsive if we needed help with something and during the initial booking process. I would recommend this place to anyone traveling to the area!

Great place to stay in Southbury!

The Barn was very nice and peaceful. It was close to restaurants and family. Suited us and our dog very well. The property is right next to a golf course and there is a deer living on the property. We saw a fox one morning as well. We really enjoyed staying at the barn.

This is a very beautiful home and grounds. Tracy and Errol are very welcoming and friendly. Guests who stay there have access to the grounds and the pool which are beautifully maintained, peaceful, and lush. My teenage grandchildren came over to visit and swim in the pool and loved the decorative details of the apartment! Tracy provided many extra little touches like providing toothbrushes. The bed was wonderfully comfortable. Overall, I can’t say enough about what a lovely place this is. 😊

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!

Blake is a kind and attentive host. The house is fun and eclectic. Many interesting things to look at, art books to leaf through and she has a great record album collection. It has all the necessities you would hope to see in an airbandb. I like the location. We enjoyed taking a hike in Mount Beacon park to see the remnants of an old casino and great views of the Hudson Valley.

We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!

The graves home was very comfortable. It was very accommodating. It had enough room for the whole family. We were not on top of each other. The beds were extremely comfortable. The last place we stayed at the beds were horrible. These were absolutely comfortable. It was very peaceful and quiet no surrounding neighbors. It was wonderful to wake up and see the deer in the backyard every morning while I was drinking my coffee. The host was great. He responded within 5 to 10 minutes every time I had no issues would definitely recommend staying here if you’re looking for a quiet, relaxing family getaway. and the pool is wonderful.

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Andrea is a super warm and responsive host. The apartment is beautiful and quiet but also very close to Main Street and everywhere you want to walk to in Beacon. Highly recommend!

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.

This place the atmosphere the surroundings it was all so lovely and needed, the price paid off. I loved the views the water and the shower outside. The bed was so comfortable very clean the place overall was very comfy I felt so comfortable. I recommend this place for a stay if you love to be away from people and need calmness. Everything was on spot from the house, the area outside to everything included. Thankyou so much for this, 10/10

Staying at this stunning Victorian home in Ossining was an absolute dream. From the moment we walked in, we felt completely at home. The house is full of warmth and character, with so many cozy sitting rooms to choose from — each one with its own unique charm. Every detail of the décor felt thoughtfully chosen, striking a perfect balance between historic charm and comfort. We especially loved relaxing on the back porch, taking in the beautiful view of the Hudson River. Jeff was a fantastic host — so friendly, easy to communicate with, and full of great local tips. His guidebook made exploring the area so much easier, and really helped us make the most of our stay. We couldn’t have asked for a better place or a better host. Highly recommend if you're looking for a special getaway with true character!

We had such a great time that we ended up booking another stay on our very first day! We came for Father’s Day weekend and were really impressed by how many thoughtful touches and recommendations were listed in the guest handbook. The dog beach was a huge hit with our puppy, and we had a blast. Thanks for helping make our vacation so special!

We really enjoyed our stay! The Airstream matched the photos and listing perfectly and is tucked in a quiet, wooded location. We were able to walk to the restaurants, small shops and the train station. Highly recommend this spot for anyone craving the nostalgia of 80s camping.

The house was peaceful and quiet in a charming town; the internet worked well; the bathrooms and kitchen are brand new and state-of-the-art. It was great to have a whole house to ourselves. Elinisa is so responsive; she replied quickly to two questions we had even before we had arrived.

Linda is such a great host! She is SUPER organized from the very beginning giving us clear instructions about the check in, the rules at the house, leaving printed version of all of that in different sides of the house, and even to the way she organized and provided everything we ever needed at that house. And the house itself is soooo gorgeous and peaceful I felt right at home. The only flaw is that it has bad reception in the area since it is surrounded by woods. But Linda provided us with strong wifi in the house, so I guess that settled it.