Vacation rentals in Weston

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…

Huckleberry Quarters, the Cozy Redding Retreat.

It’s time to book your FALL LEAF-PEEPING sojourn at 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 FALL, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

The Cozy Little Cottage

Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our 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. We have a twin air mattress for use in the living room.

Peaceful Suburban Colonial w/New Kitchen.

Looking for a clean, cozy, secluded suburban escape that's still close to great shopping, Long Island Sound, and the two Fairfield Universities? Look no further than this newly renovated colonial on a quiet tree-lined street with no through traffic. A park and basketball are just at the end of the street. Trader Joes and other great shopping are a 2 minute drive away. Sacred Heart and Fairfield U are 5 minutes away. We're right across the street in case any of us forgot anything :).

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

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.

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Sunny Westport Studio Apt. Above Historic Mill

Historic Charm Meets Modern Comfort: A Unique Studio Retreat Perched atop a restored 19th-century Cider Mill, this sunlit studio blends timeless character with modern amenities. Enjoy stunning views of a picturesque stream, serene meadows, and diverse wildlife. Just moments from Southport Village, yet offering a peaceful escape, it's perfect for history lovers, business travelers, and design enthusiasts seeking a unique getaway.

The Zen Cabin

Seated beside a playful cascade on Moffit’s Brook, this 1960 Log Cabin has been mindfully rejuvenated. 62 miles from NYC, The Zen Cabin offers respite from the hustle and bustle. Skylights, windows, and doors connect you with nature. Media-free, pet-free, and shoe-free. This laid-back retreat resides in one of Connecticut’s most bucolic and protected villages.

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.