House vacation rentals in Lewisboro

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!

Location · Family · Nearby

The Cozy Little Cottage

Charming guest apartment 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, but connected by a breezeway, and is above the garage. It is quaint and cozy, roughly 350 sq ft. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. Bedroom has a queen bed and we have a twin air mattress for use in living room.

Location · Family · Checkout

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

Location · Family · Indoor spaces

5BR Beach House, Water Views, Game Room, Backyard

Wake up to beautiful water views at this spacious 5-bedroom Stamford home, just a short walk from Cove Island Park and Beach. Enjoy a private backyard, game room, pool table, foosball and fire pit, with plenty of space for families and groups to relax, gather and have fun together. Spend your days by the beach or relaxing at home. Downtown Stamford, Metro-North, restaurants and shopping are all just a short drive away, offering the perfect mix of a peaceful coastal escape and city convenience.

Value · Family · Indoor spaces

Nature Retreat Airbnb

House located in beautiful and tranquil Redding, CT. Two floors with private deck. Main level: half-bath, cook's kitchen with a 4-person dining area, living room with flatscreen TV with an Apple TV and a view of nature. Living room convertible couch can sleep two small children or one adult. Upstairs: 2 bedrooms with full size beds, privacy blinds, bathroom w/ shower (no tub). If you want a getaway from the city, or just an escape then come to this quiet and private house in the woods.

Value · Family · Amenities

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Location · Value · Cleanliness

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.

Value · Family · Accuracy

Lakeview Estate - Chef's Kitchen - NYC Getaway

Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

Value · Family · Access

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Family · Value · Backyard

Beautifully Restored Barn With New England Charm

Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.

Family · Location · Beach

Sleeps 18 LAKE VIEWS! Perfect for large group!

*We only book to 25 or older PERFECT SPOT TO BRING YOUR BOAT! This home sleeps up to 18 people + is perfect for large groups, wedding parties or team retreats. You’ll love the sunset views, large living room and kitchen for entertaining and hanging out, pool table, dart board and large yard for games. There’s even a spot to bring your own boat or jet ski and room to park your trailer! IG stay_at_the_lake

Family · Location · Nearby

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

Family · Value · Pool