Holiday houses in Fairfield County

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…

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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.

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Huckleberry Quarters, the Cozy Redding Retreat.

It’s time to book your Winter holiday at the Huckleberry Quarters, a beautifully appointed 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 any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

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.

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Square6ix Stylish Guesthouse in Westville

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

Fern Grove Cottage

If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!

2BR Flat above Historic Cider Mill

Escape to a sun-filled, 2-bedroom artisan retreat in a restored 1850s cider mill. Overlooking a peaceful marsh near Westport & Southport, this unique space comfortably fits 4. Enjoy historic charm, modern comforts, a fully-stocked kitchen, and free access to a professional co-working space. Perfect for families, couples, or work-from-anywhere stays. Free parking included.

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.