Pet-friendly holiday rentals in Sleepy Hollow

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Sleepy Hollow pet-friendly home rentals

Pet-friendly house rentals

Top Guest favourite
Home in West Caldwell
4.96 out of 5 average rating, 156 reviews

Designer Cottage on historic estate-home away home

MariaRating, 5 stars6 days ago
Mark is an extremely responsive host. The cottage was quaint and had exactly what we needed for our stay. It was clean, and he was proactive about communication with us as well as responsive when we had questions. The area has lots of great restaurants but is still safe and quiet. We will absolutely be back as I visit the area often. Five star review!
Guest favourite
Home in Stormville
4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!
Top Guest favourite
Home in New Paltz
4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

EleonoraRating, 5 stars3 weeks ago
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍
Guest favourite
Home in Kerhonkson
4.96 out of 5 average rating, 312 reviews

Architect's Hudson Valley Home in the Woods

BaptisteRating, 5 stars4 days ago
Olga's beautiful modern house in Upstate New York is a real gem nestled near a wild forest. The spacious house offers plenty of room to relax and unwind after a day exploring the area. The location offers a perfect blend of tranquility and adventure, with plenty of things to do in the surrounding area. Olga was a fantastic host – incredibly responsive and flexible, which made our stay even more enjoyable. The house itself is stunning, with modern amenities and stylish decor. We had a wonderful stay and highly recommend this Airbnb!
Guest favourite
Home in New Paltz
4.95 out of 5 average rating, 282 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

BlairRating, 5 stars2 days ago
A very lovely place to stay! The description matched the place exactly. We enjoyed spending a lot of time outside on the deck bird watching and even saw some fish jumping in the river. The property is also very private which was a huge plus -- no visible neighbors in any direction while spending time outside. Seth was a very responsive host and did a great job with the design of the house. There were lots of thoughtful touches that made the stay extra nice. Would love to stay again!
Guest favourite
Home in Commack
4.99 out of 5 average rating, 140 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

AliceRating, 5 stars3 weeks ago
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!
Superhost
Home in Sterling Forest
4.86 out of 5 average rating, 155 reviews

Aster Place

RickyRating, 5 stars5 days ago
We had an amazing three-night stay at this lovely house on Lake Greenwood. The surroundings were absolutely beautiful, and we enjoyed every moment. The house provided great comfort, and we had some of the best nights of sleep. Highly recommend this place for a peaceful getaway!
Top Guest favourite
Home in Monroe
4.97 out of 5 average rating, 118 reviews

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

YingyingRating, 5 stars1 month ago
This is the second time we took our family here. Everything is as great as we remembered. The kids enjoyed swimming, jacuzzing, rowing the boat and playing ping pong and billiards when it is raining. Great three-day weekend well spent. The lake view is fantastic and it is 1.5 hours from Manhattan or 2 hours from Brooklyn. The rate did get more expensive comparing to two years ago but I can tell the location is still very popular from June on. I guess May is a nice shoulder season and the host allowed us to do early check in and late check out. Maybe it is more affordable to combine two families or a group of friends.

Pet-friendly home rentals with a pool

Top Guest favourite
Guesthouse in Southbury
4.93 out of 5 average rating, 322 reviews

Charming Guest Cottage with Modern Amenities

YelizaRating, 5 stars2 weeks ago
This place is absolutely gorgeous. I spent quite a bit of time just exploring the grounds with my dog. It was too cold to use the pool but it was still beautiful to look at and a nice view while I was cooking/washing dishes. I appreciate the tour I received when I arrived to show me around. I would definitely recommend this place and hope to book again in the future.
Top Guest favourite
Barn in West Orange
4.85 out of 5 average rating, 162 reviews

Quaint Converted Barn

EricaRating, 5 stars2 days ago
Another peaceful stay at this property. This Airbnb has everything. Definitely a home away from home. Did I mention there’s a pool to cool off in the summer! Nature and everything you will need. Just walk with yourself and clothing. Erica
Guest favourite
Apartment in Stony Point
4.88 out of 5 average rating, 185 reviews

E and T Getaway LLC

JoelRating, 5 stars3 months ago
I would highly recommend this place, Tracy was very helpful. She gave us clear instructions. She had the place prepared for us. She even customized for us a card and guiding us to where everything is, the place was very clean, very well taken care of, and a lot of thoughts went into designing this place with all the amenities and comfortabilities
Guest favourite
Home in Warwick
4.92 out of 5 average rating, 109 reviews

Summer Retreat! Amazing Pool, Playground, 7 acres!

JohanyRating, 5 stars3 weeks ago
This property is large and roomy with plenty beds to go around including the basement with the pool and ping pong tables plus a home gym with various equipments. The outdoors were fantastic with a very nice temperature controlled pool, Jacuzzi, swings set for the little ones and enough acreage to have a soccer match. The neighborhood was nice and quiet in a great country setting with lots of wildlife to enjoy to include lots of singing birds. Our family reunion was a great success due in part to the before mentioned surroundings. Douglas was always available to resolve minor issues, very responsive and accommodating, thanks for making our stay at this property a great one.
Guest favourite
Cottage in Pine Bush
4.89 out of 5 average rating, 268 reviews

Seclusion and Romance - Pool is open and heated!

OwenRating, 5 stars3 weeks ago
Great place for a quick stop on a trip to visit family. Super communicative and friendly. Would stay again!
Guest favourite
Guest suite in Holmes
4.97 out of 5 average rating, 195 reviews

Prvt pool Huge, Eclectic space… 1.5 hr to NYC!

PatriciaRating, 5 stars4 weeks ago
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.
Superhost
Cabin in Kerhonkson
4.95 out of 5 average rating, 148 reviews

Pool - Hot Tub - Game Room - Mini Golf - Country

IvanRating, 5 stars3 weeks ago
Had a great stay! The place was clean, comfortable, and exactly as described. Check-in was smooth, and communication with the host was easy and responsive. The location was convenient and quiet—perfect for a relaxing getaway. Would definitely stay here again!
Top Guest favourite
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars3 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.

Private, pet-friendly home rentals

Guest favourite
Cottage in Putnam Valley
4.96 out of 5 average rating, 166 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

MadelineRating, 5 stars2 days ago
Benjamin's place is all you expect and more. It is clean, roomy, comfortable, and quiet. My family is all about comfortable temperatures and the AC makes each room feel great. If you are sitting on the deck, off the kitchen, there is a breeze with pretty sunrises and sunsets. Ben was a thoughtful host! I reached out with one simple question and before we knew it we had items delivered to the door - for our family and our dog! It was a delightful and welcoming touch. The cottage is so comfortable with fabulous bedding, a fantastic Jacuzzi tub, a fully stocked kitchen, and a full coffee and tea bar! Such a generous amenity. I highly recommend Benjamin's cottage.
Superhost
Cottage in Carmel Hamlet
4.83 out of 5 average rating, 162 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

ErinRating, 5 stars4 days 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 favourite
Cottage in Newtown
4.93 out of 5 average rating, 256 reviews

Private and Serene home close to I-84 and shopping

LauraRating, 5 stars3 days ago
Very communicative and perfect description of what was expected.
Top Guest favourite
Farm stay in Fort Montgomery
4.98 out of 5 average rating, 195 reviews

Secluded overlook cottage near West Point

LuciaRating, 5 stars2 weeks ago
We had a great stay, Linda’s place is amazing, quiet and beautiful surroundings very peaceful. Communication was great and the place was just as pictured
Guest favourite
Cabin in New Milford
4.95 out of 5 average rating, 171 reviews

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

VanessaRating, 5 stars1 week ago
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
Guest favourite
Farm stay in New Paltz
4.91 out of 5 average rating, 725 reviews

The 1772 Lefevre Stonehouse Suite

SamanthaRating, 5 stars2 weeks ago
The room was comfortable and clean, we enjoyed our stay and would stay again!
Guest favourite
Cabin in Vernon Valley
4.96 out of 5 average rating, 419 reviews

Serenity Cabin, the historic waterfall cabin!

TessRating, 5 stars2 weeks ago
Great 1 night stay after a lovely hike at Stairway To Heaven. Hosts were super responsive and sweet. The cottage was so cute and tucked away from the other neighboring houses.
Guest favourite
Guest suite in New Paltz
4.9 out of 5 average rating, 137 reviews

Newly built apartment steps from Mohonk preserve.

AndrewRating, 5 stars2 weeks ago
Staying at Merlin's was great. I enjoyed the quiet and the beautiful surroundings. Merlin is friendly and accommodating, if needed. Though i didn't need anything, he was always available, if i needed. I world definitely try and book again, if I'm in the area. The place was cozy and charming.

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