Family-friendly vacation rentals in Pine Plains

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Top-rated family-friendly rentals in Pine Plains

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Guest favourite

Cottage in Pine Plains

5.0 out of 5 average rating, 132 reviews

Patchin Mills Quaint Country Cottage

Welcome to your cozy cottage in the bucolic Hudson Valley. Only 90 mi. north of NYC. We welcome small dogs, under 25 lbs. with prior host approval. Sorry, NO CATS. Enjoy biking, hiking, skiing, local culture or just relaxing. 1 mile outside a charming village in farm and horse country, your cottage has a full kitchen/LR, 2 BRS (1 queen, 1 full), bathrm, washer/dryer, deck, patio & yard. Close to colleges, dining & activities. We hope that you will love this corner of the world as much as we do.

Feb. 25 – Mar. 4

$274 CAD per night

Guest favourite

Guest suite in Millerton

4.93 out of 5 average rating, 322 reviews

Romantic Sunset-50 mile view!

ROMANTIC LUXURY! Spring/Summer is beginning now. Flowers are starting to bloom and the nights are crisp and cool. Fresh mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV;

Aug. 22 – 29

$262 CAD per night

Guest favourite

Cottage in Hillsdale

4.83 out of 5 average rating, 235 reviews

Big Bliss Near Catamount Cottage w/Modern Flair

Find big bliss and sanctuary in every detail of this newly renovated cottage. The tranquil view of our yard and neighbor's orchard are complemented by the whitewashed wood floors and Moroccan tiled kitchen. The heated bathroom floor, Toto bidet, and central air/heat elevate to indulgence. Nestled between Hudson, NY, and the Berkshires, our cozy home is the perfect getaway with culture close by. Hiking trails and Catamount a short drive away. Search "Little Bliss" for our adjacent tiny house.

Oct. 7 – 14

$235 CAD per night

Guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

May 2 – 9

$251 CAD per night

Guest favourite

Guest suite in Red Hook

4.9 out of 5 average rating, 299 reviews

the farmhouse suite at gallatin farmstead

A 575 sq ft. fully private suite with your own entrance in a beautiful early American eyebrow colonial. The mid-century farmhouse style is highlighted by a darling kitchenette. And don't forget the bathroom hot steam shower! Of note, with a 30$ fee, we can set up a 2nd bed in the suite living room. We're happy to do it, it just takes some time to get together. It's a super comfortable mattress, the same model as the queen bed. We are also cycling happy and offer bike rentals and tours.

Jan. 12 – 19

$228 CAD per night

Guest favourite

Cottage in Craryville

4.91 out of 5 average rating, 482 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking.

Mar. 16 – 23

$185 CAD per night

Guest favourite

Tiny homes 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!

Jul. 10 – 17

$168 CAD per night

Guest favourite

Home in New Paltz

4.97 out of 5 average rating, 679 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.

Feb. 19 – 26

$189 CAD per night

Guest favourite

Home in Copake

4.92 out of 5 average rating, 107 reviews

Copake Retreat

Our cozy 3 bedroom home is 120 miles from New York City and 150 miles from Boston. It's located in a friendly private lakeside community with 2 sandy beaches on Robinson Pond. The surrounding area is gorgeous with rolling hills and farms. We're within a half-hour drive from Great Barrington, MA., Hudson, NY, and Millerton, NY. and it's a very short drive to Taconic State Park. Enjoy our 4-season Copake Retreat!

Sep. 21 – 28

$255 CAD per night

Guest favourite

Apartment in Millerton

4.8 out of 5 average rating, 231 reviews

Gardens Galore and Village Whimsy Retreat

My place is close to restaurants and dining, the city center, and parks. My place is good for couples, solo adventurers, business travelers, and families (with kids). It is a steal for the price. nothing is as good around here, a true bargin. The apartment is below the 1850's victorian house. During the day you can hear children's feet pitter patter. After 7 The place is quite.

Jan. 13 – 20

$155 CAD per night

Guest favourite

Cottage in Copake Falls

4.91 out of 5 average rating, 317 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Dec. 23 – 30

$247 CAD per night

Guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 305 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Sep. 25 – Oct. 2

$698 CAD per night