Family-friendly holiday rentals in Woodbury

My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

Beautiful house, gorgeous and convenient location, excellent host. We had a great stay.

Jeannine’s home was an absolute gem! We had our annual girls weekend here and felt right at home. The house was so cozy and warm yet had ample space for me and the girls to sit and chat together. We loved that the house was lived in with family photos and mementos around, rather than being sterile like many other bnbs we’ve stayed in. There was also so much to do in the surrounding area! I would definitely recommend this stay :)

We enjoyed our 2-night stay at Enrique's Rhinebeck home. It's out in the country, very peaceful, and very quiet at night. About an 8 minute drive to the charming town of Rhinebeck. We were out riding the rail trails during the day, but when at the house, really enjoyed the deck, hot tub, and screened porch (later at night when it got buggy). The kitchen is well appointed. Bedrooms and bathrooms are on the smaller side. Definitely would consider staying here again if ever back in the Rhinebeck area.

Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!

What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

We loved Jane's cozy home. The hot tub is perfect and has the best view.

We really enjoyed staying here, only wish we booked it for longer! Our son and our dog enjoyed going for walks on the trails behind the brewery. The beers and pizza from the brewery were excellent, the house is really charming and relaxing. Also got out to enjoy the disc golf course which was a fun way to spend the afternoon. I would love to come back and try out the mountain bike trails. The surrounding area was fun to explore, really can't think of any negative points to this place!

Noel’s third floor apartment is light-filled, spacious, has a cute rustic vibe and is perfectly located. It’s across the street from East Rock Park (great for walks and runs) and walking distance to restaurants and an ice cream shop. The entrance to the apartment is through Noel‘s home – – no private entrance. Parking was incredibly easy—right on the street in front of the house! We enjoyed our stay very much, especially thoughtful touches like breakfast muffins and coffee. The apartment is full of interesting books and games and is very comfortable. Noel is a helpful host.

We loved our stay here. It was the perfect place for two of us and our dog. The home was just as described, welcoming, cosy and well equipped, and we appreciated all the local recommendations. We enjoyed local walks, the lake, and the great dog park, as well as easy access to Middletown to visit our son. Elisabeth and Daniel were fantastic hosts!

Cail and Jayne were great hosts! Their farmhouse was beautiful and the grounds were lovely! They were very responsive when we needed to contact them. The house had everything we needed. It was the perfect home base for our daughter's graduation from the University of New Haven!

I stayed at this place for my husband's birthday, The house is beautiful and very quiet, I loved the interior and the view. The only things you need to be aware is the AC is located in the living room, inside the room you need to use fans or leave the door open

Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!

We lived in the Hudson Valley before retiring to Maine. For the past 4 years, Sarah and Jonathan’s home has provided the perfect spot for return visits with family and friends and a comfortable place away from home. The house is tastefully decorated and provides all that we require for an extended stay. The kitchen is well appointed with utensils, dishware, pans, and a large assortment of appliances. A special feature in the home is the lower level room with a huge wrap-around couch, large screen tv and toys for the kids. In addition, the grounds are beautiful. The outside deck allows for time to enjoy the gorgeous view and the large yard is fun for romps with our little Havanese. Being close to the town is an added bonus: The Tribute Gardens, Marona’s Market, the little French restaurant (Cafe Les Beaux), Stewart’s for ice cream, The Merritt Bookstore + Toystore, various antique shops are places we frequent. Innisfree Gardens and Dover Stone Church are nearby. We love it here!

Gabriele's place was a great place to stay! We really liked the furnishings. When I messed up, Gabrielle was in constant touch with us so we could get everything right. She is a wonderful host

We had a great stay here as we explored nearby things (the Chuang Yen Monastery was delightful!) and visited some favorite spots. The weather was a little dreary when we were there, otherwise we would have made good use of the beautiful outdoor space. It was the perfect place for us to relax after our adventures every day—very quiet, very comfortable, clearly-written instructions for everything. We would be very happy to return!

My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.

Alice’s place was great! We’ll be back again for sure.

Only complaint would be the noise from road during the morning commute

We had an incredible time at Kathleen’s home! It was just lovely! Spotless clean and had everything you would need for a great stay! Kathleen was very responsive and communicative! We were there for our daughter’s graduation at Vassar college and it worked out perfectly. I highly recommend this beautiful home for a stay! We can’t wait to return! Many thanks, Kathleen! Allison & Chris