Family-friendly vacation rentals in Sharon

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Top-rated family-friendly rentals in Sharon

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

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Guest favorite

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 9 – 16

G$33,454 GYD per night

Guest favorite

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.

Jun 24 – Jul 1

G$35,616 GYD per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 351 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Aug 24 – 31

G$84,309 GYD per night

Guest favorite

Guest suite in Red Hook

4.9 out of 5 average rating, 300 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 10 – 17

G$34,670 GYD per night

Guest favorite

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!

Jul 16 – 23

G$22,952 GYD per night

Guest favorite

Home in Cornwall

4.92 out of 5 average rating, 229 reviews

Secluded modern forest cabin with private brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

Aug 1 – 8

G$48,784 GYD per night

Guest favorite

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.

Apr 3 – 10

G$27,481 GYD per night

Guest favorite

Apartment in Millerton

4.8 out of 5 average rating, 232 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 23 – 30

G$21,378 GYD per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 340 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

Mar 17 – 24

G$20,495 GYD per night

Guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 306 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.

Aug 22 – 29

G$97,147 GYD per night

Guest favorite

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.

Jan 11 – 18

G$34,217 GYD per night

Guest favorite

Home in Millerton

4.88 out of 5 average rating, 137 reviews

The 1913 House, book 6 days get the 7th free.

Cozy turn of the century house, recently renovated, and minutes from historic downtown Millerton. Close to area attractions including: Millbrook Hunt Country, area clubs, local schools (Hotchkiss, IMS, Millbrook School, and Salisbury Boys School), dozens of Hudson Valley farms and farmstands, and multiple ski resorts.

Oct 28 – Nov 4

G$47,712 GYD per night