What Guests Are Saying About Their Fairfield County Stay
“Meeker Hill House was a beautiful place for a winter getaway to visit family. The huge fireplace was a special treat and if you’re lucky enough to have a full moon as we did — wow what a sight out back at night! Although we didn’t have the weather to utilize the back patio and pool, they are so beautiful and can imagine what a retreat this home would be in the summer. The kitchen is very well stocked for cooking — even a rolling pin for baking gingerbread cookies with grandchildren!”
“Yes, this place looks exactly like the pictures — and it truly is that stunning Connecticut getaway with a picture-perfect lawn view and a sleek, modern pool. What the photos don’t show you is how it feels: like you’re staying at your impossibly chic friend’s house while they’re away traveling (probably in Paris for Fashion Week and staying at Costes). You open the fridge and, to your surprise, there’s a bottle of Cristal — surely a mistake, you think. Forgot your moisturizer? Don’t worry, there’s Barbara Sturm everywhere. From the impeccably stocked liquor cabinet to the most comfortable hybrid mattress, every detail is a notch above what you’d expect from an Airbnb — right down to the stack of plush Loewe pool towels casually waiting for you in just when you think they forgot something.”
“Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend”
“We really enjoyed our stay. The space was beautifully designed and pristine. It was a calming and relaxing space to return to after a full day of team building. Would definitely recommend!”
“This place is a gem. The house is beautiful and well-appointed and the grounds and pool are spectacular. Each bedroom has its own private bath which makes renting with couples super easy and comfortable. It’s just an extremely relaxing and beautiful place if you’re looking for a quiet escape.”
“We absolutely loved our stay in Redding. The house is so tastefully done. Not overdone. Simple and beautiful. The pool was perfect, the property is breathtaking and our family can’t wait to return. We fell in love with the doors in this house! Bravo to the owners.”
Discover Fairfield County
Fairfield County packs coastline, preserved forests, and some of the best small-town energy in the Northeast into a stretch of southwestern Connecticut that starts less than an hour from Midtown. It’s the kind of place where a single weekend can include a beach morning, a trail in the afternoon, and a restaurant that rivals anything in the city by evening.
Sherwood Island State Park is the standout: a wide stretch of sand and tidal marsh right on Long Island Sound, with views that open up and keep going. Compo Beach in Westport and Penfield Beach in Fairfield are local favorites for a low-key afternoon by the water, and Calf Pasture Beach in Norwalk adds a boardwalk and playground to the mix for families. On calmer days, launch a kayak from one of the harbors in Norwalk or Southport and explore the coastline from the water. Several of our Fairfield County homes put you within a short drive of the shoreline, so a morning beach walk and a quiet afternoon back at the pool is an easy kind of day to build.
Devil’s Den Preserve in Weston is 1,756 acres of forest trails, rocky ridges, and wildlife corridors managed by The Nature Conservancy, and it’s the largest nature preserve in Fairfield County. Weir Farm National Historical Park in Wilton and Ridgefield is worth a visit for its gentle trails and painter’s landscape. The Paugussett State Forest, Trout Brook Valley Preserve, and the Aspetuck Land Trust network of trails add plenty of options when you want a longer hike or a quick morning walk before coffee.
Westport’s downtown is a genuine draw: bookstores, independent boutiques, galleries, and some of the county’s best restaurants within an easy walk. Ridgefield’s Main Street has a slower, more residential energy with the Aldrich Contemporary Art Museum anchoring the cultural end. New Canaan blends mid-century architectural history with an upscale village center. Darien and Southport are quieter, perfect for a stroll and a good lunch. With a Red Cottage home as your base, you can town-hop all day and still be back in time to cook dinner in your rental kitchen.
The Aldrich Contemporary Art Museum in Ridgefield is a standout for modern exhibitions in an intimate, walkable setting. Silvermine Arts Center in New Canaan hosts rotating shows and open studios worth planning around. The Maritime Aquarium in Norwalk is a solid half-day destination for families, and the Lockwood-Mathews Mansion Museum in Norwalk offers a window into the area’s Gilded Age past. Farmers’ markets run through the warmer months in nearly every town, and stocking your rental kitchen with local produce is one of the better ways to spend a Saturday morning.
The Whelk in Westport is a seafood destination worth planning a night around, with a raw bar and waterfront setting that deliver without trying too hard. Terrain in Westport pairs garden-center browsing with a polished lunch that feels like an event in itself. Tavern at GrayBarns in Silvermine is another strong option for a relaxed, elevated dinner. For something more casual, Match Burger Lobster in Westport or Rowayton Seafood in Norwalk deliver solid meals without the fuss.