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Kid-friendly holiday rentals in Dutchess County

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Top-rated family-friendly rentals in Dutchess County

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Flat

5 out of 5 average rating, 3 reviews

Esopus Creekfront Game Room Family Fire Pit Kayaks

Welcome to Upstate Waterfronts! Whether you're traveling for the Holidays, visiting family, or looking for a restorative Upstate getaway - this Creekside gem has you covered. - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Guest favourite

Home

4.95 out of 5 average rating, 110 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favourite

Cottage

4.99 out of 5 average rating, 140 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Cottage

4.9 out of 5 average rating, 202 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you. BE SURE TO SEE OUR OTHER 2 BEDROOM COTTAGE ON THE LAKE - LILY PAD - IF YOUR DATES ARE NOT AVAILABLE.

Guest favourite

Home

4.93 out of 5 average rating, 212 reviews

3Br Creekside Cottage on 130 acre forest w/ trails

Creekside Cottage is an extraordinary private escape nestled against a winding creek running through the rocky gorge of an 130 acre magical historic farm. Explore miles of hiking trails through old forests, trout creeks, and a 90ft waterfall or simply relax by the fire pit while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplaces, great wifi and comfortable bedrooms with quiet workspaces- learn more on our site cascadafarm

Apartment

4.92 out of 5 average rating, 136 reviews

Cozy & walking distance to cafés *holiday avails*

Perfect for friends, couples, families, or solo-travelers looking for a comfortable home that’s centrally located and near some of Kingston’s best restaurants and shops! This historic two-unit home is walking distance to the waterfront and a short drive to incredible hikes and farms! *Pet-friendly (no extra fee) *Family-friendly (highchair + Pack n Play for babies, games for kids). Note: Parking onsite or arrive via Metro North to Poughkeepsie, Amtrak to Rhinebeck, or bus to Kingston

Guest favourite

Home

4.95 out of 5 average rating, 112 reviews

Magical Waterfront Escape on the Esopus Creek

Magical and creative! Get ready for the most unique and one of the most popular properties in the Hudson Valley for over 18 years. With 150 feet of frontage on the Esopus Creek in the back of the property and the rolling hills and barns of an organic farm in the front. Tranquility dominates the views seen from every vantage point of this gorgeous house located at the base of the Catskill mountains. Truly the coziest little getaway perfect to escape all the hustle and bustle of life!

Guest favourite

Farm stay

4.88 out of 5 average rating, 297 reviews

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

Cottage

4.86 out of 5 average rating, 207 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

Equipped with essentials such as air conditioning, cleaning products, cooking basics, and a dedicated workspace. Guests can prepare meals in the fully equipped kitchen, which includes dishes, silverware, and cooking utensils, dishwasher, and microwave. A washer and dryer, hair dryer, heating, and hot tub are also available for guests' use. 2 Min – Appalachian Trail 4 Min - Kent Town center 9 Min – Kent falls 10 Min - Bulls Bridge 19 Min - Mohawk Mountain Ski Area

Guest favourite

Home

4.98 out of 5 average rating, 120 reviews

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

Cottage

4.8 out of 5 average rating, 189 reviews

Cozy Country Cottage Spa/Fireplace/Enclosed Yard

Quaint/rustic, former carriage house vibe on scenic, country road, surrounded by 90 acres of park land/nature preserve across the road. Beautiful/scenic setting w/ stream views from porch/deck/patio; minutes from hiking/shopping/fishing/boating, train to station and village waterfront. Loaded with amenities, including basketball court, pellet stove, jacuzzi, swing set, sand box, tree swing, wood fire pits, central ac, and fully enclosed yard.

Guest favourite

Home

4.97 out of 5 average rating, 155 reviews

Vacation Home In Millerton

This is a house to enjoy with the family with a lot of space and many activities, in a small town but with a lot of tourism. You can visit the town which it has a small cinema, and Rail trail for walking or biking, and it has many restaurants nearby. This house includes a living room, kitchen, 4 bedrooms, 3 full bathrooms, deck, and a big backyard. You can also do BBQ s outside.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Flats

Convenient locations with everyday essentials

Popular amenities for Dutchess County family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home

4.89 out of 5 average rating, 505 reviews

Cozy ranch near FDR Historical Site

Guest favourite

Home

5 out of 5 average rating, 215 reviews

Hobbit House of Pawling

Home

4.75 out of 5 average rating, 175 reviews

Historic 1 BR Family Home Near Buttermilk Falls

Home

4.89 out of 5 average rating, 95 reviews

Rhinebeck retreat

Guest favourite

Home

5 out of 5 average rating, 107 reviews

Stunning Views, Light and Open - The Beech House

Home

4.76 out of 5 average rating, 174 reviews

Gorgeous country hideout with views close to all ✨

Guest favourite

Home

4.91 out of 5 average rating, 253 reviews

1834 Farm House

Home

4.91 out of 5 average rating, 178 reviews

New 3b House in Saugerties Village/4 mins to HITs

Family-friendly apartment rentals

Guest favourite

Flat

4.94 out of 5 average rating, 329 reviews

3 Bdrm. Near Hudson Valley Colleges & Attractions

Flat

4.83 out of 5 average rating, 626 reviews

Top Floor 2BR - Just Renovated!

Guest favourite

Flat

4.98 out of 5 average rating, 178 reviews

Renovated apartment in midtown Kingston

Guest favourite

Flat

5 out of 5 average rating, 202 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

Guest favourite

Flat

4.95 out of 5 average rating, 132 reviews

Large, private apartment in scenic Hudson Valley

Flat

4.76 out of 5 average rating, 202 reviews

Rhinebeck Village Apartment

Guest favourite

Flat

4.89 out of 5 average rating, 282 reviews

Getaway or Artist's Retreat w/In-Unit Laundry

Guest favourite

Flat

4.98 out of 5 average rating, 121 reviews

1 Bedroom with Backyard & Front Porch, Central Air

Family-friendly apartment rentals

Guest favourite

Apartment

4.98 out of 5 average rating, 159 reviews

Stylish Private Studio 1 block from Main St Beacon

Guest favourite

Apartment

4.96 out of 5 average rating, 283 reviews

Spacious and stylish entire one bedroom apartment.

Guest favourite

Apartment

4.99 out of 5 average rating, 544 reviews

Rustic Spa Retreat

Guest favourite

Private room

4.86 out of 5 average rating, 152 reviews

Hudson Valley Hiker’s Loft-Private Room Queen Bed

Destinations to explore