Vacation rentals in Tavern Island

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

S. Norwalk Studio Apt near the water!

Newly-built sunny studio apartment with separate eat-in kithchen and spacious bath, across the street from the water in the peaceful waterfront community of Shorefront Park in South Norwalk. 20 min walk to South Norwalk shops, restaraunts and the train station (65 min train ride to NYC). Private kepypad entrance, washer/dryer, eat-in kitchen, free off-street parking, wifi, central AC. 2 night minimum Please note the house next door may be under construction. Please inquire for current status.

Nice Colonial, EV Charger, Patio BBQ, SoNo, Beach

Enjoy a cozy retreat in Norwalk with your family and friends! 5-min drive to Calf Pasture Beach, a highlight of the town with a skate park, playground, restaurant, and basketball court. Whole House Water Filtration + Alkaline Drinking Water Right next to SoNo, a beautiful coastal area with an aquarium and the main hub for restaurants Close to train to Grand Central (don’t worry, it’s quiet!) Full kitchen and private patio, ready for BBQ parking 500 Mbps WiFi (really fast) Tesla charger

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

Sunny French Cottage

This unique, sunny cottage has it's own style. Private and peaceful, completely renovated cottage with French vibes. Originally used as a painting/design studio. It is an ideal place to relax and enjoy the surrounding nature. The upstairs bedroom is loft style and has a luxurious queen size bed. It's ideal for short and long stays. It is a perfect place for cozy evenings and lazy mornings, it can also serve as a temporary workplace. High tea style, organic breakfast available (20$ per person)

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

Waterfront Getaway - Norwalk, CT

Enjoy a stylish experience at this prime location - ideal to explore, relax, or WFH. This beautiful seaside home has full direct waterfront views of the Norwalk Harbor and LI Sound from every room and a balcony. NYC is a quick ride away, with a train station just 0.4 miles away. Across the street is our lovely Veteran's Memorial Park with a route going to Calf Pasture Beach! Experience fine dining in SoNO, long lines at Mr. Frosty's Ice Cream, and more. You won't want to miss this experience.

Van Zant Townhouse Apt #2

Enjoy a stylish experience at this centrally-located Brand New Townhouse. This Townhouse offers well over 1100 square feet of living space, which includes 2 bedrooms, 1.5 bathrooms, large living room, eat-in kitchen and laundry room, plus 2 cars garage. This convenient location offers 5 minutes walk to SONO bars and restaurants, SoNo Collection shopping mall, Metro North Train Station and waterfront parks. Minutes away from I-95 and 50 minutes away from NYC Grand Central on express train.

Enchanting Guest Cottage

Your own cozy cottage nestled away in the most charming, historical part of Fairfield. Where the sounds of the babbling brook lull you to sleep and baby deer peek from behind the lush trees. Serene and enchanting, this 1940s bungalow is bursting with original details and warmth. A one minute drive to the most divine chocolatier, as well as fine dining at Bonda, all your snack needs at the Corner Market. Perfect for a quiet retreat when coming back to nature and beauty fills your soul.

5BR Beach House, Game Room + Huge Backyard

Escape to this spacious 5-bedroom Shippan beach home, designed for families and groups to relax, reconnect and have fun together. Just a short walk from West Beach, the home features a huge private fenced backyard, two large decks, fire pit, game room, pool table, ping pong, foosball and plenty of indoor and outdoor space for everyone to spread out Located just minutes from Downtown Stamford and Metro-North, it’s an ideal home base for family getaways, group stays and corporate retreats

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

The Perch: Saltwater Pool Woodland Cottage Retreat

*Pool closes for the season on Sept 15 and reopens May 2027* inquire for details The Perch, a design-forward woodland cottage surrounded by nature just one hour from NYC perfect for couples escaping the city for a quiet Hudson Valley weekend. Spend slow mornings overlooking the woods, afternoons by the saltwater pool, and evenings exploring Bedford’s historic village restaurants and trails. "The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa