Family-friendly vacation rentals in Woodbury

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Popular amenities for Woodbury family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in East Stroudsburg
4.92 out of 5 average rating, 189 reviews

Big House On The Hill - Hot Tub, Sauna, Fireplace!

NatielaRating, 5 stars2 months ago
From the beginning Ting and Ning had excellent communication that made the booking experience at their rental extremely easy. My questions were answered in a timely manner and the instructions were clear. The home was beautiful and the comfort was so manageable that my guests and i were so sad for it to end. The fruit when we walked in was much needed because we were starving. The home was such a great experience and i would definitely book with Ting and Ning again. Thank you for such an amazing weekend!!!
Top guest favourite
Home in Rhinebeck
4.91 out of 5 average rating, 230 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

AudreyRating, 5 stars1 month ago
Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!
Superhost
Home in Long Pond
4.81 out of 5 average rating, 256 reviews

Fantastic Luxury home 6 Bed room *HOT TUB* *LINEN

StephanieRating, 5 stars2 weeks ago
Great place to stay
Superhost
Home in Olivebridge
4.92 out of 5 average rating, 454 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

SamanthaRating, 5 stars3 weeks ago
Our stay here was everything and more. The pictures don’t do this home justice. We felt right at home and our dog had the best time adventuring around the property. We plan on coming back! Super responsive host and instructions around the home to make sure you have 0 questions.
Guest favourite
Chalet in Jewett
4.97 out of 5 average rating, 182 reviews

Private Catskills Home w. Hot Tub, near Ski Mnt

Gina-LouiseRating, 5 stars1 month ago
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!
Superhost
Cabin in Swan Lake
4.82 out of 5 average rating, 201 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

SarahRating, 5 stars1 month ago
Beautiful cabin, particularly liked the huge windows to watch the sunset and hawks swooping by, the wood-burning stove and the hot tub! Anna was very helpful when the power very briefly went off. Lots of towels and everything you could need in the kitchen. Had a great stay!
Guest favourite
Home in Elizaville
4.86 out of 5 average rating, 100 reviews

Peaceful Hudson Valley Retreat House with HOT TUB!

AndreaRating, 5 stars2 months ago
Beautiful and comfortable home, warm and cozy in the winter. Our group of friends had a lovely stay and can't wait to go back.
Top guest favourite
Home in Saugerties
4.96 out of 5 average rating, 163 reviews

Lux 1800's renovated farmhouse w/hot tub+pool

PaulRating, 5 stars3 months ago
Loved the house. Kitchen is great. Awesome living room with very comfortable couch and fireplace. Bedrooms perfect. Hot tub was perfect. Original Nintendo system upstairs was fun. Went skiing at Hunter which is 20-25 min away. Woodstock 15 min away. Really a great place. Jaime was responsive, friendly and helpful.

Family- and pet-friendly home rentals

Guest favourite
Cottage in Roxbury
4.9 out of 5 average rating, 130 reviews

Bellwood Cottage 8-14min to all Roxbury Wed Venues

LaurenRating, 5 stars5 months ago
House was great location, very comfortable- Kimberlie was awesome, thanks for your kindness. Lauren N
Guest favourite
Cabin in Woodstock
4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

JosephRating, 5 stars1 month ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Guest favourite
Home in Bushkill
4.92 out of 5 average rating, 201 reviews

Entire House Hot tub Barrel Sauna Private Backyard

PietroRating, 5 stars3 months ago
I have been to many places but this house was top notch I'm glad I got to stay there with my family. everyone was very happy with the property. I would like to stay in the summer as well
Guest favourite
Apartment in Carmel-by-the-Sea
4.87 out of 5 average rating, 295 reviews

Private space, with yard

MoiraRating, 5 stars1 month ago
Nice location Pet friendly Clean and the host we’re always available to answer any questions you had Would stay there again!
Top guest favourite
Apartment in Clinton Hill
4.98 out of 5 average rating, 116 reviews

Family brownstone with backyard

JohnRating, 5 stars1 week ago
We had the absolute pleasure of staying in Peter’s beautiful brownstone for our family engagement weekend, and it truly exceeded all expectations. From the moment we arrived, Peter made us feel incredibly welcome. The home is full of classic New York charm, with stylish, modern touches that made it both elegant and inviting. The space was spotless, the kitchen well-stocked, and every detail clearly thought through to create a comfortable and relaxing stay. The neighborhood was vibrant and full of character, yet peaceful enough for quiet mornings with coffee. Peter went above and beyond to make sure we had everything we needed. This brownstone will always hold a special place in our hearts. We’re so grateful to Peter for his hospitality and would absolutely stay here again. Highly recommend!
Guest favourite
Home in Windham
4.91 out of 5 average rating, 155 reviews

Serendipity Lake House on Lake Heloise

PenelopeRating, 5 stars1 month ago
Very large and nice open space in the house. Family of 6 felt very comfortable and we could have had more join. Quick drive to windham to ski and spent evenings in front of fire playing cards. Kitchen has everything you need for nights in.
Superhost
Home in West Kill
4.93 out of 5 average rating, 121 reviews

Catskill Mountain Cabin Waterfall Retreat

TatyanaRating, 5 stars2 months ago
I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.
Guest favourite
Cabin in Prattsville
4.83 out of 5 average rating, 169 reviews

Modern Cabin w/Swimming, Boats, HOT TUB & VIEWS!

SaraRating, 5 stars2 months ago
We had an amazing weekend stay at Catherine and Diego’s modern cabin! The property is exactly as described—beautiful, cozy, and perfect for a group getaway, with charming wood paneling and all the comforts of home. The hot tub and stunning views of the snow-covered landscape were highlights, creating a peaceful and relaxing atmosphere after a day out. The location was ideal, offering both privacy and proximity to skiing and other activities, and the hosts provided clear instructions for check-in, making the experience stress-free. We’d highly recommend this cabin to anyone looking for a quiet, cozy escape in the mountains!

Family-friendly home rentals with a pool

Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars1 month ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Tobyhanna
4.8 out of 5 average rating, 129 reviews

Cozy home for 10 ~ Private pool, BBQ, fire pit

EsteeRating, 5 stars2 months ago
We had a wonderful stay at this house. It was clean, spacious, very warm despite the cold, and had a terrific pool table and air hockey table. Our family relaxed and spent good time together.
Guest favourite
Cottage in West Orange
4.87 out of 5 average rating, 202 reviews

Cozy Pool Cottage

PaulRating, 5 stars3 months ago
We have stayed here several times. The Cottage has everything we need and Micaela has always been responsive to our questions. The location is quiet and easy to get to.
Guest favourite
Home in Saugerties
4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars6 months ago
We had a terrific stay. The house was exactly as advertised.
Guest favourite
Home in Englewood
4.93 out of 5 average rating, 151 reviews

Englewood NJ Country Carriage House (15 min NYC)

EnithRating, 5 stars1 month ago
We were absolutely delighted with this house. Lisa is an amazing host—always very attentive and with excellent communication. She is kind, cheerful, and that truly reflects in her home. Her house is simply beautiful, filled with wonderful details. There are all kinds of different mugs in the kitchen, collected from various places. Masks from all over the world. The house is colorful and full of life. The steam room and sauna worked perfectly. The beds were incredibly comfortable. I highly recommend this place, and without a doubt, I’ll be coming back soon—because I won’t be choosing any other house
Guest favourite
Cabin in East Stroudsburg
4.88 out of 5 average rating, 129 reviews

Pocono cabin with POOL at Shawnee Mtn

Yossi Rating, 5 stars3 weeks ago
If you're after something warm and cozy, this is your spot! It easily fits a family of four and comes with everything you need. The views around the cabin are stunning, and the outdoor space is perfect! there’s a hot Jacuzzi always ready, a fire pit, two chill sitting areas, a big deck, and a massive pool. really recommend!
Guest favourite
Home in Cold Spring
4.95 out of 5 average rating, 166 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

ChristopherRating, 5 stars1 month ago
We had a peaceful and relaxing stay at Shawna’s beautiful Cold Spring country-style home. We were in town for a family gathering and accommodations, cleanliness and Shawn’s communication were five star. We absolutely recommend the house and Shawna as a host for you to stay with!
Guest favourite
Home in Hudson
4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

JakeRating, 5 stars6 months ago
Amazing amazing for a birthday weekend. Good proximity to Hudson while still feeling in the woods. So clean and cozy.

Quick stats about vacation rentals that are family-friendly in Woodbury

  • Total rentals

    30 properties

  • Nightly prices starting at

    $69 CAD before taxes and fees

  • Total number of reviews

    840 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore