Family-friendly vacation rentals in Weston

Huckleberry Quarters, the Cozy Redding Retreat.

Time to book your summer getaway or STAYCATION with the Huckleberry Quarters, a beautifully renovated studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy this summer, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

Sticks and Stones Farm - The Solar Cabin

Sticks and Stones Farm offers a rustic glamping experience! When you stay with us you'll get the adventure and fun of camping (no electricity, outdoor showers etc.) while still getting to lay your head on a soft pillow in a bed. You can treat your stay here as a chance to go inward or enjoy interacting with the different programs and events going on! If you want to be up to date on events or ask about weekday checkins you can message us directly.

Top Rated Gem | Fire Pit | BBQ | FFU | Near Beach

Welcome to Fairfield Cottage, a cozy retreat that beautifully combines comfort and stylish design for you and your guests. With thoughtful decor and essential amenities, you'll feel right at home. Conveniently located just 90 minutes to NYC, you can easily visit attractions like the Norwalk Aquarium, Beardsley Zoo, and local farms. Unwind at nearby Jennings and Penfield beaches located just 3 miles away, or explore the charming village of Southport.

Sunny Westport 2 BR Retreat above Historic Mill

Historic Cider Mill Retreat – A Unique Stay for Leisure & Business Travelers Experience the charm of history blended seamlessly with modern comfort in this eclectic, sun-filled apartment perched atop a beautifully restored 1850s cider mill. Thoughtfully designed and furnished by our team of artisans, this unique getaway offers panoramic views, breathtaking surroundings, and a rich historical ambiance that makes for a truly unforgettable stay.

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.