
Family-friendly holiday rentals in Crawford
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Top-rated family-friendly rentals in Crawford
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Family-friendly home rentals with a hot tub

2 BR , Fireplace & Hot Tub @ heart of Woodstock
What a peaceful wonderful time we had in this cherry red cabin. Thank you for warm healing waters, sunny blue skies with mountain views, cozy sleeps and wonderful times cooking and gathering around the cozy cabin. We unplugged, biked the reservoir, ate lots of yummy veggie food, danced at the Bearsville Theater, and breathed in the magical mountain air. Thanks Woodstock and much gratitude to our host Mirav for creating a wonderful retreat. Blessings.

Secluded Artist's Retreat with Hot tub
We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!

Rhinebeck Home with an amazing outdoor space+H/tub
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!

Mountain-Top Catskills Getaway Cabin w/hot tub
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.

Make it your home away from home
I had a great time at Tracy’s place. The house was really new (much better than the photos). Location was amazing!

Renovated Country Cottage w/ Hot Tub & View
Gorgeous house, super clean and tidy inside, with comfy and modern furniture. The hot tub was fantastic, make sure you turn off the lights so you can see the stars! The only other heads up I’ll give is that the way to get in is through the back entrance! We tried the front door for like 5 minutes until the electronic lock blocked us from continuing haha. Great location to get away from the city for a weekend and go hiking. Lots of great trails really close by.

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

Log Cabin * Hot Tub * Sauna * 4.6 mi. Bethel Woods
Julie's place was the perfect winter getaway. The fireplace, hot tub and sauna warmed us and the very well-equipped kitchen enabled us to prepare great meals. The house was beautiful, with two living rooms for different activities and energy levels, a game room downstairs, a dining room with a large table and chairs, and comfortable furniture and beds throughout. Julie texted me to make sure that our every need was met. We had a snow and ice storm, and she had the driveway and walkways plowed, shoveled and sanded twice, and kept plenty of salt on-hand. We hope to return sometime in warmer weather so we can enjoy the pond, too.
Family- and pet-friendly home rentals

Stunning Modern Barn minutes from Woodstock 21N195
A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.

Peace Cottage
I booked Nidhi's place for one night for myself and a guest to attend a show at Bearsville. The placement of everything, inside and outside, created an intentional sense of comfort. My guest arrived after me - without a thought, we ended up at the kitchen table talking for hours before the show. Again, the placement of this conversation spot felt intentional, but only after we found ourselves engaged in it. The outdoor surroundings are utilized to not only accent, but to enhance the indoor setting. The whole experience felt private and safe, and allowed us to share a really precious window of time for reconnection and decompression. In addition to the appealing aesthetics (the chosen blue for that kitchen!), the bedding was a treat to come back to at the end of the night - so inviting and equally comforting to find yourself wrapped up in in the morning. Nidhi so kindly messaged me out of concern for the very high winds we were experiencing (prepared with a generator), but no issue.

A Cozy’s Woodstock Getaway Home
This space is so lovely, the hot tub worked perfectly and provided many cozy nights outside. The plants are BEAUTIFULLY tender and bring a loving atmosphere to the space. the linen sheets were so wonderful at the end of the day. we made it up the hill in a Honda insight, but if it were a tiny bit icy I don't think we would have been able to make it. definitely use 4wd if you have it. the hosts were very responsive. if the noise is too much in the bedroom at night (critters, rain,etc.) be sure to use the fan they provide, it helped us a lot :) the kitchen was a delight to use. sharp knives. big, metal surfaces. nice gas stove. big fridge.

Rock City Writer's Studio: bucolic•sauna•walkable!
Super close to town! Lovely setting. Fun to take a shower under a skylight. As others have said, it’s very compact! Would be an ideal place for a person to get away to write.

Welcome to Malden Manor, in a prime location!
Lovely place in Saugerties, close to lots of great hiking and restaurants.

Wallkill Inn
This house was nice, steap stars. one hour away from all three locations JW branches.

Entire lake house to yourself. Great for groups
Scott's place was great. We were so relaxed and felt right at home. We will be going back which is the best compliment I can give an AirBnB. The views were beautiful!

Pet Friendly Cabin Doh-Ray up at 1450 ft
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Family-friendly home rentals with a pool

midcentury mod * POOL * walk out trail to mohonk
Susan’s home is wonderful. The layout of the house was perfect. We had my elderly parents with us and we did not feel at all as if we were on top of each other. The kitchen was also perfect for a small group to entertain and was loaded with amenities! Everything was spotless and exceptionally clean. It’s very close of the village of New Paltz (3 min. car ride) where the restaurants and shopping is located. We also had a nice view of Mohonk Mountain! All in all it was a perfect and peaceful getaway weekend in the mountains!

Spacious Staycation near HITS & the Hudson
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

5BR close to Village | Diamond Mills | HITS | Pool
Overall the place was very nice to stay at. Hosts/Property manager were EXCELLENT communicators (we had an issues and they had solutions within 30 minutes). Close to supermarket (right down the street), along with close to being downtown Saugerties, resturants and getting on the thruway. Would recommend for families.

Modern Upstate Cabin, near Rhinebeck NY
We loved celebrating my wife’s birthday at Tina’s home with our bichon frisée! Her home was so peaceful and we loved relaxing in the soaking tub, listening to music, and unwinding. It was the perfect weekend for staying in and reading books while surrounded by nature (and rain!). The home was easy to find and had everything you could need for a snuggly weekend in. We loved Red Hook - we have never explored it before! The shops are adorable. We hope to be back when it’s warmer to try the pool!

MODERN FARMHOUSE in the WOODS
We had a terrific stay. The house was exactly as advertised.

Majestic Oasis Rhinebeck - Hot Tub, Sauna, & Pool
This was the perfect place for a weekend away from the city with a few couples. The hosts were so communicative and hospitable from the moment we arrived, ensuring we had what we needed (including sharing some amazing farm fresh eggs!). Our group loves to cook and the kitchen is an amazing space for friends to cook and hang out. We even had some fun using the pool table. The bedrooms were all perfectly comfortable and the bathrooms notably had great water pressure. Our dog also loved getting to run around outside in nature on the property. Location was very close to Rhinebeck where you’ll find tons of cute local stores and restaurants. We are already discussing coming back with friends this summer!

FREE Amenity Passes Spacious Sauna Lrg Deck Firepi
Our stay at this property was nothing short of excellent! From the moment we arrived, we were impressed by the beautiful ambiance and attention to detail throughout the home. Every room was comfortable, well-appointed, and loved by everyone in our group. The property was clean, inviting, and had everything we needed for a relaxing getaway. The host was responsive and accommodating, ensuring our stay was seamless. We truly enjoyed every moment and would highly recommend this Airbnb to anyone looking for a fantastic place to stay. We can’t wait to return!

Lovely Creekside w pool/sauna near Woodstock
We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.
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- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Bushkill Falls
- The Kartrite Resort & Indoor Waterpark
- Promised Land State Park
- Resorts World Catskills
- Delaware Water Gap National Recreation Area
- Thunder Ridge Ski Area
- Rockland Lake State Park
- Hook Mountain State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Great Falls Park
- Campgaw Mountain Ski Area
- Ringwood State Park
- The Ridgewood Country Club
- Tamarack Country Club
- Opus 40
- Thaddeus Hait Farm
- Hopatcong State Park
- Mountain Ridge Country Club