Holiday houses in Westbrook

Adorable single story cottage-by-the-sea

Adorable, quiet seasonal single story cottage-by-the-sea, in Westbrook, CT. The cottage is located approximately 25 yards from private West Beach. You will love the large front porch and living room with plenty of space for everyone. Updated kitchen with all the amenities. Two bedrooms with closets & drawers. Picnic bench with stainless steel grille & Bonfire Solo Stove outside. Hot & cold outdoor shower to wash off the sand, after a day at the beach. Off road parking on the side of the house.

Value · Family · Decor

Adorable Cottage, 5 min walk to water & coffee

Experience the quaint charm of our Westbrook, CT, with this adorable coastal retreat just a 3 minute walk to middle beach. Ideal for traveling workers, couples, or small families, this 2-bedroom, 1-bath unit was recently renovated with light, bright touches! Guests can also enjoy an outdoor fire pit and grill. Included is a TV for entertainment, free internet for remote work and driveway parking for convenience. Consider renting our other unit for larger families at this sweet beach community.

Location · Family · Indoor spaces

Remodeled cozy home near beach

.4 mile walk to Beach/Westbrook Elks Club, this newly remodeled home is perfect for a couple looking to relax and enjoy what the CT Shoreline has to offer. Close to restaurants and shopping, this house boasts a spacious queen bedroom, walk in shower, large kitchen, living room, dining room, sitting area, 2 gas fireplaces, & laundry room. Enjoy the private outdoor deck with dining table, Adirondack chairs, porch swing and hot tub. Cook outside on the Weber grill or take a ride on bikes provided.

Location · Family · Cleanliness

Secret Seaside Stone Cottage

Create unforgettable memories at the Secret Stone Cottage, a retreat in the scenic coastal town of Westbrook, Connecticut. Offering 2,200 SF of refined living space and outdoor living amenities along the serene Patchogue River, this unique property is the ultimate destination for family reunions, shared vacations, and milestone celebrations. With sweeping waterfront views and sophisticated amenities, it also serves as an enchanting, intimate venue for unforgettable weddings and special events.

Location · Value · Backyard

Coastal Westbrook Loft Vaulted Ceilings & Lvl 2 EV

Kick back in this bright and spacious 2nd-floor apartment, perfectly situated for your Connecticut shoreline getaway. The first thing you’ll notice are the stunning vaulted ceilings, which give the space an open, airy vibe that feels instantly relaxing. Whether you’re in town for a beach weekend or a remote work week, you’ll love the modern conveniences, including a 55" TV for movie nights and a dedicated EV charger—a rare find that makes road-tripping with your electric vehicle a breeze.

Location · Hospitality · Accuracy

Beachside @ 455 Seaside

Welcome to the Connecticut shoreline and this cozy ranch-style beach home located in one of Westbrook’s sandy beach communities. Unwind on the front deck while enjoying water views. The home is just a short walk to the Town Beach, which features a fishing pier, and playground. You’ll also have access to a nearby neighborhood beach that offers a bit more privacy. Summer stays are offered as weekly rentals. Whether you’re here for a beach getaway or a work stay, we’d love to host you.

Location · Family · Kitchen

Sea Salt Air Changes Everything

Sea Salt Air Changes Everything... The mood. The conversation. The momentum. When you are here you will find yourself at the crossroads of nature and civilization. Stroll to a private association beach from this restful retreat. Stretch out on the deck overlooking swaying seagrass. Sing in the outdoor shower. Go on, no one is listening. Tasteful appointments. Elegance abounds. Salt life refined with the comforts that nourish your soul. Solitude awaits you.

Family · Location · Amenities

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Location · Value · Nearby

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Value · Location · Check-in

King Suite, Easy walk to Beach

A modern coastal retreat in the heart of Westbrook. Perfectly curated for couples or solo travelers, our king suite offers a seamless blend of charm and modern luxury. Located just a short, easy walk to the sands of West Beach, it’s the ultimate home base for your next shoreline getaway! Air-Conditioning, High-speed WiFi and more included.

Family · Location · Indoor spaces

The Nest

Our warm and inviting studio apartment with bright and cheery decor offers a cozy get away any time of year. Nestled in a peaceful country neighborhood with endless hiking trails, beaches, and cozy villages nearby. The Nest offers a comfortable and convenient place to stay while enjoying the surrounding area.

Family · Value · Bathroom

Family-Friendly Cottage by The Shore

Welcome to our cottage in Westbrook, CT! A clean, comfortable and convenient spot to stay so you are free to explore and relax. Beautiful beaches, shopping and entertainment all around makes for the perfect home base for your stay.

Family · Location · Outdoor spaces