
Kid-friendly holiday rentals in Dutchess County
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Top-rated family-friendly rentals in Dutchess County
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Kid-friendly house rentals

Ideal for students and those who travel for work.
Overall a perfect place to crash for a night or two when in the area. It was quiet and clean. Our only issue was the bed- it’s very soft so of that’s not for you, you may not get a good night’s rest. But mainly the sides are somewhat sloped so I would start to fall toward the floor unless I pushed myself way back into the center. This may not be an issue for a single person, but for two it was. Otherwise a great spot!

Cozy ranch near FDR Historical Site
Cynthia was quick to respond to questions I sent. House was nicely appointed, with a good selection of hot and cold beverage choices and snacks. Beds and pillows were comfortable and the house is roomy enough for four adults to stay comfortably. Proximity to National Park sites was unbeatable.

Private Hudson Valley Country Retreat
Our second time here. Great spot for our family of 4, and Sandy is very responsive

Welcome to Your Hudson Valley Escape
My girlfriends and I had a lovely stay at Mary & Jeff’s house. It is a gorgeous home and the craftsmanship to remodel the home is seen in every room. It is a bright, open home that is so relaxing to spend a long weekend there. 10-15 min drive to Rhinebeck. I’d highly recommend this gorgeous home and property for a Hudson Valley getaway! Everything about this stay was easy and relaxing!

Lux Bungalow on the Lake
This was a few nights getaway with my two adult daughters. The house is adorable, neat and cozy. The beds were very comfortable. Felt right at home. We did a little kayaking on the lake, which was beautiful. The weather wasn’t perfect, but we made the best of it and enjoyed each other’s company. The neighborhood was very quaint. We took a walk around the lake. Nicole was very responsive whenever I messaged her. We felt very comfortable being there. I would highly recommend this home.

3BR/3BA Renovated Retreat w/ Firepit By Rhinebeck
This is a lovely house, which is much larger on the inside than it appears from the outside. It would be perfect for a family or a girls weekend or a few couples. Marisa was very responsive when we had any questions.

Stunning Views, Light and Open - The Beech House
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!

Cozy Historic Piersaull House - Charming & Quirky!
This house is exactly as described, comfortable, cozy and has everything you need for a great visit. The bedrooms were so comfortable. Our weather wasn’t the best so we were disappointed we could not use the outdoor fire pit. There was no parking in the front because there was always cars there so we did have to park quite far up the road, but that’s not any fault of the owners. I would highly recommend this if you are visiting the area Marist, the CIA or Vassar, it’s a great option instead of an overpriced hotel. Highly recommend!
Family-friendly apartment rentals

Newly Restored 2BR
Graham's 2-bedroom apartment within walking distance to downtown Beacon was perfect for a quick weekend getaway from the city for our family of 3. The apartment was exactly as pictured, and was very stylish and spotless. The location was quiet and we were not bothered by any road noise at night. We enjoyed walking into town on the railroad tracks for dinner and breakfast. Will definitely try to book again when in the area.

3 Bdrm. Near Hudson Valley Colleges & Attractions
Really cute place, one of those that is actually better in person than in the posting! Very spacious and lovely place that hits the balance of modern comfort and honoring the old beauty of the high ceilings, molding, etc. super easy experience and great for our reunion weekend. Thank you!

*The Ridge House*
We had a great time at The Ridge House! The property was gorgeous, and the creek is even more stunning in person. The apartment was clean, fresh, and felt very cozy. The kitchen was well stocked to make a meal. Instructions were clear and we had no logistical issues. Thanks for great stay!

Arcady - Modern, 1br cottage
We spent a peaceful five days relaxing in the beautiful surroundings of this cabin. Steven graciously accepted our last minute reservation and also our request to extend our stay since we were having such a lovely time. No one was staying in the main house while we were there so we had the grounds to ourselves. The cabin itself is spotless and minimalist, with everything you need to cook in the modern kitchen or grill outside. We stayed with our pup and enjoyed walking him five minutes down the road to explore the town park (we had it to ourselves in mid-May but imagine it’s much busier during the summer). WiFi is super fast and we were able to work remotely without issue.

Cozy private apartment in Rhinebeck Village
We loved our stay at Frank's place - the house is so cosy and characterful, and the location is beautiful. It's a really easy walk to the shops and restaurants of lovely Rhinebeck. The small balcony around the back was a very nice surprise. Frank is a really friendly and helpful host and has equipped the apartment so well. Thanks for a great stay!

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️
We had a wonderful stay! The place was spotless and incredibly well-prepared. The host went above and beyond—there was a bottle of wine and a charcuterie board waiting for us when we arrived, which was such a thoughtful touch. She truly thought of everything we might need, from toiletries to kitchen essentials, including a variety of snacks/breakfast items, coffee and teas. It made our stay comfortable, relaxing and stress-free. Highly recommend and would definitely stay again!

Cozy Hudson Valley Retreat | 1800s Farmhouse
Our group went on a hiking trip to Beacon, and this was a nice stay, though about 20+ minutes to town. But we didn't mind the drive! It felt very safe and the second floor of the farmhouse was a peaceful retreat! The hosts were super responsive. The house was clean, beds were very comfortable, and the house was full of books and character! You can tell the hosts put a lot of love in decorating, making each space feel thought through and unique. The 2.5 bathrooms was nice for our group of 4 ladies! Thanks again!

Charming Pet Friendly Getaway w Hot Tub & Fire Pit
This place was great. Super simple check in/check out. Louis was great with communications. Great location and everything was clean. Would def recommend and/or stay again.
Family-friendly apartment rentals

Spacious and stylish entire one bedroom apartment.
Michelle’s place was wonderful, an awesome deal for its quality and how close it was to downtown. Extremely clean, and Michelle actively checked in to ensure the stay was going well. Would definitely recommend.

Rustic Spa Retreat
Dan’s place is cozy, comfortable and just minutes away from Mt. Beacon in one direction and ten minutes away from Main Street in the other direction. The kitchen is stocked with cooking essentials, though there are so many delicious restaurants nearby- the best of both worlds! The bed was extremely comfortable and the jetted bathtub was a huge bonus. I genuinely relaxed there, which is a rarity for me. Thanks so much, Dan!

Cozy & walking distance to cafés *spring avails*
Cozy apartment, walking distance from the water front. Had a great weekend getaway.

Hudson Valley Hiker’s Loft-Private Room Queen Bed
I had a great stay! Super comfortable bed, room had everything I needed, and the AC unit kept my room very comfortable on the 90 degree day! Henry & Jorge were both very kind and easy to be around. If you're looking for a comfy bed in a comfortable space, this is perfect!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Windham Mountain
- Resorts World Catskills
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Rockland Lake State Park
- Hudson Highlands State Park
- Zoom Flume
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Sterling Forest State Park
- The Connecticut Golf Club
- Hunter Mountain Resort
- Mount Peter Ski Area
- The Stanwich Club
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Hancock Shaker Village
- Things to do Dutchess County
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