Family-friendly holiday rentals in Blooming Grove

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Top-rated family-friendly rentals in Blooming Grove

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

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Guest favourite

Guest suite in Montgomery

4.95 out of 5 average rating, 422 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

21–28 Nov

$175 SGD per night

Guest favourite

Guest house in Warwick

4.96 out of 5 average rating, 249 reviews

Bellvale Guest House on Solar Powered Mini-estate

Town of Warwick Short Term Rental Permit #32553 Come spend a relaxing week-end on our 4 acre mini-estate in beautiful Warwick, about one hour from NYC. Our detached 2 bedroom guest apartment is in a secluded setting, yet boasts spectacular views of the Warwick Valley. There are numerous attractions for all tastes including craft breweries and wineries. Close to home, Mt Peter Ski Area is within walking distance and further up the mountain is the nationally famous Bellvale Farms Creamery.

9–16 Mar

$263 SGD per night

Guest favourite

Flat in New Paltz

4.96 out of 5 average rating, 346 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

25 Feb – 4 Mar

$155 SGD per night

Guest favourite

Guest suite in Cold Spring

4.79 out of 5 average rating, 484 reviews

Cozy getaway in Cold Spring

Sweet studio attached to our house w/updated kitchen & bathroom on a dead-end street backed up to a nature preserve. We have parking for those arriving by car & are a block from the train if coming up from the city. Walking distance to everything (Main St is 2 blocks away!) We welcome all types of folks and your lovely pets as well. We're here for your needs & offer as much contact or privacy as you like! In the summer, an outdoor shower is available to you as well through the backyard.

21–28 Feb

$204 SGD per night

Guest favourite

Tiny home in New Paltz

4.99 out of 5 average rating, 744 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

10–17 Jul

$149 SGD per night

Guest favourite

Flat in Chester

4.96 out of 5 average rating, 335 reviews

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

11–18 Mar

$214 SGD per night

Guest favourite

Home in New Paltz

4.97 out of 5 average rating, 680 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

19–26 Apr

$178 SGD per night

Guest favourite

Farm stay in Goshen

4.85 out of 5 average rating, 295 reviews

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away

28 Feb – 7 Mar

$347 SGD per night

Guest favourite

Flat in Beacon

4.99 out of 5 average rating, 487 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

19–26 Jul

$253 SGD per night

Guest favourite

Home in New Windsor

4.89 out of 5 average rating, 103 reviews

View House

Magnificent views from this octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city <3. * The place has been renovated for 2023, with new kitchen and appliances. Photos still being uploaded.

18–25 Feb

$383 SGD per night

Guest favourite

Flat in Cold Spring

4.95 out of 5 average rating, 522 reviews

Beautiful loft space

Located in the heart of Cold Spring, NY, this beautiful architect-designed loft space is only 2 blocks away from the Metro North train stop. It features a large single bedroom, a full kitchen, a full dining table and chairs, and a sleeper sofa.

12–19 Dec

$276 SGD per night