
Family-friendly vacation rentals in Dutchess County
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Top-rated family-friendly rentals in Dutchess County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Amenia Main St Cozy Studio
Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Hoppy Hill Farm House
Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Large, private apartment in scenic Hudson Valley
We are located right in the middle of the Dutchess County so access to all points is convenient. Many attractions are: historical Hyde Park, Walkway Over The Hudson, Culinary Institute, Vassar & Marist colleges, wineries, breweries, the quaint towns of Millbrook & Rhinebeck, Dutchess County Fairgrounds, and The Links At Unionvale golf course and banquet hall. Great for couples, adventurers and business travelers who love activity but appreciate a comfortable quiet place at the end of the day.

Quiet Studio Apartment in Pawling
For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

Private ground floor guest suite in Hudson Valley
Newly renovated private, ground floor guest suite returning for 2025 rentals! Br, full bath, large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen.

Spacious and stylish entire one bedroom apartment.
Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

Spilt Milk Cottage - Hudson Valley, NY
Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Newly renovated cutie
Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Spacious Studio in Historic home, near Metro North
1st floor studio apartment in a private home. Located in the historic Mt Carmel/Little Italy section of Poughkeepsie. 5 minute walk to Metro North train station and entrance to the Walkway over the Hudson. Many restaurants, coffee/pastry shops within walking distance. There is off street parking and a lovely yard in back. Convenient to Marist College, Vassar College, the CIA, FDR home , Vanderbilt Mansion, Locust Grove, breweries, Rail trails and Wineries. NO third party booking allowed.

Village Cape Getaway
Village Cape on Albany Post Rd in the historic town of Hyde Park. Surrounded by gardens, stone walls, private parking/entry. This 2 story house offers a 1 bdrm apartment that sleeps 3 on the 2nd floor. Close to markets, shops, restaurants. 1 mi to Vanderbilt Mansion, FDR house and library. 2mi to the Culinary Institute of America. 4mi to Marist College. Hiking trails walking distance. Historic drive-in movie in town. Metro north Poughkeepsie sta 6mi south offering taxi and bus service.

Lake Side Tiny House
Reconnect with nature at this unforgettable escape. Sitting on a beautiful 5 acre property, tucked back in the woods along a beautiful lake. Come stay and unwind. Plenty to explore and just be. Lake access for swimming or with paddle board, canoe, or kayak. Just ask and can be assisted with. The whole property has been curated to be a playground. Full bathroom inside unit. Brand new Mini Split heat and AC unit. Works amazing Has most kitchen amenities besides an oven. Enjoy

Pine Plains Cottage
Located just 2 hours north of NYC, our country cottage in bucolic Pine Plains is newly renovated and furnished in a modern yet cozy style, welcoming you to a relaxing retreat! It is located in the heart of Pine Plains, a short walk to the town center. Perfect for 2-4 people. We currently have a 2 night min. stay and 3 night min. for holiday weekends. Contact us directly for week/month/shorter stays and to inquire if we can accommodate your pet or a shorter stay!
Popular amenities for Dutchess County family-friendly rentals
Family-friendly home rentals with a hot tub

Waterfront Three bedroom in Saugerties w/ Hot Tub

Bluestone Escape - Where everyone is at home.

(°) The Wandering Peacock (°)

Unwind in the country, stargaze in hot tub

4Br Mountain Brook House on 130 acres w/ trails

Cozy Mountainside Suite - Minutes from Beacon

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Peaceful Riverfront Cottage with Private Hot tub
Family- and pet-friendly home rentals

Honeybug Snug near Omega Institute!

Vacation Home In Millerton

Deluxe Mtn Loft, Oct leaves changing colors.

Charming Guest Suite in the Hudson Valley

Your Own Pied-a-Terre "WALKWAY OVER THE HUDSON"#2

Serene Retreat with Outdoor Firepit and Pond Views

Hyde Parks Hideaway

Modern farmhouse in Hudson Valley
Family-friendly home rentals with a pool

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

Fireplace, Huge Eclectic space… 1.5 hr to NYC!

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Modern Upstate Cabin, near Rhinebeck NY

Eco Cottage in the Woods

The Harvest Guest House~ Hidden Gem with Pool

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Hudson River views with pool and hot tub
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- Family-friendly rentals New York
- Family-friendly rentals United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Windham Mountain
- Resorts World Catskills
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Rockland Lake State Park
- Norman Rockwell Museum
- Taconic State Park
- Sterling Forest State Park
- Mount Peter Ski Area
- Mount Southington Ski Area
- Mohawk Mountain Ski Area
- Opus 40
- Beartown State Forest
- Talcott Mountain State Park
- Hunter Mountain Resort
- Things to do Dutchess County
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- Things to do United States
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