Nearby treasures for the perfect quick getaway
Feeling like you need a little break, but your wallet’s saying “nope.” Or the idea of a TSA line sends you into a cold sweat. Whether you’re in the mood for luxury, adventure, culture or just a cozy weekend away from the everyday, these nearby destinations have something for every kind of staycationer. So, why not play tourist in your own town? You might just fall in love with your hometown all over again.
Greenwich: Classic Elegance & Coastal Charm
For a high-end staycation with a touch of New England charm, Greenwich is the place to be. Check into The J House Greenwich, a stylish boutique hotel known for its modern design, tech-savvy rooms and vibrant atmosphere. Or book a room at the uber elegant Delamar Greenwich Harbor, where you can indulge in a gourmet meal at the hotel’s restaurant, l’escale, where the French-inspired cuisine and harbor views transport you straight to the South of France. For a luxurious spa day, consider the The Spa at Delamar Greenwich Harbor. It offers a range of rejuvenating treatments, including the signature aromatherapy massages and facials, providing a perfect escape for ultimate relaxation.
Fairfield: Family Fun & Laid-Back Escapes
Fairfield is a fantastic place for a family-friendly staycation or a casual getaway. Stay at The Delamar Southport, where the newly renovated rooms and proximity to the beach make for a perfect coastal retreat. If you’re craving adventure, take a winter beach walk at Jennings Beach or explore the exhibits at the Fairfield Museum and History Center. Grab a pizza from Colony Grill (because a staycation calls for indulgence) and end your day with a cozy movie night at The Fairfield Theatre Company, which often hosts indie films and live music. For a facial like no other, consider a booking some me-time at Priva MedSpa of Fairfield.
Ridgefield: A Quiet Country Escape
Need a true escape from it all? Ridgefield’s country charm makes it a dreamy winter retreat. Book a night at the charming West Lane Inn, then spend your day exploring the Aldrich Contemporary Art Museum. If you love the outdoors, winter hikes at Weir Farm National Historic Park offer a peaceful respite. Cozy up with dinner at Bailey’s Backyard, a farm-to-table restaurant that feels like home. For a relaxing spa experience, visit The Salt Cave of Darien, which is a short drive away, and offers halotherapy.
New Canaan: Small-Town Charm & Cozy Retreats
For a quiet, idyllic staycation, New Canaan offers a perfect mix of nature and sophistication. Check into the Roger Sherman Inn, a historic retreat with charm to spare. Take a scenic walk at Waveny Park, where rolling meadows and tree-lined paths make for a dreamy escape. Relax afterward with a cup of something cozy at Zumbach’s Gourmet Coffee, a local favorite known for its small-batch roasts. Cap off your staycation with dinner at Elm, an upscale yet inviting spot known for its creative, locally-sourced menu.
Gems Beyond Connecticut
If you’re willing to venture just outside of Fairfield County, here are three great spots nearby:
Tarrytown, NY: Stay at the The Mansion at Glen Cove, a dreamy hilltop retreat with old-world charm, luxurious spa treatments and breathtaking Hudson River views. Explore the charming Main Street or take a scenic walk at Rockefeller State Park Preserve.
Hudson, NY: A haven for art lovers and foodies, Hudson boasts serene boutique hotels like Wildflower Farms, Auberge Resorts Collection and a buzzing restaurant scene. Stroll through Warren Street’s antique shops and art galleries before enjoying rustic Italian fare at feast & floret.
Newport, RI: A little further out, but well worth the trip, Newport offers Gilded Age glamour with mansions, stunning coastal walks and charming boutique hotels like the Hammets Hotel right on the wharf. Take a stroll along the Cliff Walk before hitting a delicious waterfront seafood spot.
Montauk, NY: Embrace coastal charm at Gurney’s Montauk Resort & Seawater Spa, offering stunning ocean views and a relaxing spa experience. Explore the iconic Montauk Lighthouse, take a beach walk, and enjoy fresh seafood at a local restaurant.
The Berkshires, MA: Indulge like a royal at Canyon Ranch Lenox, a Michelin Key hotel. During the winter, take advantage of the proximity to excellent skiing at nearby Jiminy Peak Mountain Resort, offering diverse slopes for all skill levels. In the fall, immerse yourself in the breathtaking foliage by driving along the scenic Mohawk Trail, or hiking trails within the beautiful Berkshire hills.