Cozy season is approaching. In the spirit of hunkering down, we’ve assembled a selection of dreamy homes from top vacation destinations from the top agents across the country for your inspiration.

In the market for a getaway of your own? We have strong referral partnerships with agents across the country. Contact us for an introduction to a top agent you’ll love working with.

Westport, CT

Tucked away on a private cul-de-sac just minutes from downtown Westport, beaches, and award-winning restaurants, this 6-bedroom, 8-bath residence combines modern architectural design with serene natural surroundings. Set on beautifully landscaped grounds, the property backs onto a gentle brook, creating a peaceful, retreat-like setting. Once home to a celebrated local artist, the interiors showcase striking contemporary details, clean lines, and light-filled spaces designed for both entertaining and everyday living. Highlights include a rooftop deck with sweeping views, multiple flexible living spaces, and a seamless connection between indoors and out. With six spacious bedrooms, eight baths, and thoughtful design throughout, this home balances creativity, comfort, and convenience in one of Westport's most sought-after locations.

19A Darbrook Road, Westport, CT 06880

6 bed | 8 bath | 7,754 sq ft

$2,850,000

Represented by:

Nanci Lewis | Keller Williams Gold Coast

Email: nancilewis@kw.com

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New York City, NY

Perched high on the 25th floor at One Manhattan Square, awaits Residence 25D. This is the most sought-after two-bedroom line in the building, boasting exclusive southeast and southwest exposures with breathtaking unobstructed panoramic views of the East River, Manhattan and Brooklyn Bridges, the downtown skyline, and New York Harbor.

Flooded with natural light from floor-to-ceiling windows, every room is a showcase of the ever-changing New York City landscape. Whether you're watching the sunrise over the water or the glow of city lights at dusk, this residence offers a living experience like no other—elevated, expansive, and truly one-of-a-kind.

1 MANHATTAN SQUARE, #25D

2 BED | 42 BATH | 1,123 SQ FT

$2,339,900

Represented by:

The Steer Kelly Team | KW New York City

Email: nyc@steerkelly.com

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Kapalua, Maui

Experience the pinnacle of Maui resort living at Montage Residences Kapalua Bay. Residence 5102 is a spacious 3-bedroom, 3.5-bathroom home highlighted with captivating ocean views and convenient ground-floor location with private yard perfectly suited for young families and pet-lovers – and with a private “short cut” access to Kapalua Bay. From watching humpback whales in season to enjoying magical sunsets while preparing dinner at your private bbq, every moment here is framed by natural beauty. This fully furnished residence blends refined island design with all the comforts of home, and owners enjoy access to Montage’s world-class amenities including pools, spa, fitness center, and exceptional dining. Located within the renowned Kapalua Resort, you’ll find pristine beaches such as Kapalua Bay, Ironwoods, and DT Fleming, plus championship golf, hiking trails, tennis, and an array of fine restaurants just moments away.