Holiday rentals in Westbrook

A bright living area features two gray sofas with decorative pillows, a wooden coffee table, and soft yellow curtains framing the windows. A skylight allows natural light to fill the space. Decorative wall art and a clock enhance the inviting ambiance.

4.99 out of 5 average rating, 79 reviews

Home Away From Home

This cape style house is placed in a discrete location with easy access to local activities, cuisine, and I-95. The property is located within walking distance of the famous Lenny & Joe’s FishTale, Coastline Brewing Company with an open outdoor area, and Westbrook’s local Dairy Queen. Just a few minutes North is the famous Bill’s Seafood; known for their waterside dining & singing bridge. Westbrook is located right on Long Island Sound with numerous scenic areas and a plethora of entertainment.

5 out of 5 average rating, 49 reviews

Secret Seaside Stone Cottage

Create unforgettable memories at the Secret Stone Cottage, your ideal retreat for family reunions or shared vacations in this scenic coastal New England town of Westbrook, Ct . Enjoy 2200 sq. ft. of living space nestled on the Patchogue River, with private dock access to Long Island Sound. Picture evenings spent grilling by the fireplace on the expansive patio, relaxing in the hot tub, or exploring the water by kayak and paddleboard....or a quick bike ride to beaches and restaurants.

A collage showcases the various entertainment and relaxation areas. The top left features a game room with arcade machines and a dartboard. The top right highlights a manicured putting green. The bottom left displays the exterior of the home with outdoor seating, while the bottom right depicts a home gym with workout equipment against a bright orange wall.

5 out of 5 average rating, 23 reviews

Beachside Bliss w/ Game Room, Gym & Golf Green

Escape to this family-friendly retreat just steps from the beach and 2 miles from the heart of Westbrook, CT. Perfect for work or play, the home features a dedicated workspace, high-speed WiFi, a private workout area, and a fun game room for all ages. Enjoy the backyard fire pit and putting green, or explore nearby shoreline towns, shops, and restaurants. Whether you're here for a getaway or working vacation, this home has everything you need to relax and recharge.

The inviting entrance of the cottage is shown, featuring a front porch and path bordered by lush greenery. Vibrant flowers add color to the landscape, while a warm glow emanates from the entryway, highlighted by the soft evening sky.

4.97 out of 5 average rating, 70 reviews

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.

4.74 out of 5 average rating, 244 reviews

A charming entrance is framed by an archway adorned with decorative ironwork. The door, painted in a soft turquoise, is complemented by a welcoming wreath. Lush green foliage surrounds the entryway, creating a serene outdoor environment.

Cottage in Old Saybrook

The Cottage

Step into a piece of history with this charming, fully converted 1930s changing house. Ideally located, it’s just a short stroll to downtown or a scenic bike ride to the beach, putting the best of the area right at your doorstep. Inside, you’ll discover a thoughtfully designed studio layout, offering the perfect setting for a peaceful getaway. The Cottage seamlessly blends comfort, convenience, and character, creating a truly inviting retreat.

The image presents a serene beach scene, featuring a sandy pathway leading to a calm water body. A safety barrier is visible in the water, marking designated swimming areas. Lush green grass borders the beach, enhancing the tranquil coastal environment.

4.93 out of 5 average rating, 76 reviews

Zion's Light Beach Cottage

YEAR ROUND BEACH HOUSE. Unwind and make memories at Zion’s Light Beach Cottage. Westbrook, CT. Private beach association. This 2 bed, 1 bath has been designed with coastal comfort in mind. Open concept. Modern and fully equipped. Lux bedding. Dine in or patio style. Gas grill. Outdoor shower. All within a 3 minute walk to the beach. Heading out? The CT Shoreline has plenty to do. Check out our guidebook!

4.94 out of 5 average rating, 89 reviews

A well-lit guest suite features a spacious bed against a neutral wall. A cozy seating area with a patterned chair is present, alongside a light-colored rug on the wooden floor. Large windows allow natural light to fill the room, creating an airy atmosphere.

Guest suite in Westbrook

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.

Guest suite in Saybrook Manor

A bright living space features vaulted ceilings and modern light fixtures. Two armchairs are positioned beside a wooden table with a decorative plant. A television is mounted on the wall, and natural light filters through sheer curtains, enhancing the inviting ambiance.

4.98 out of 5 average rating, 107 reviews

Cozy Loft Getaway

Our private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

4.97 out of 5 average rating, 124 reviews

An open studio layout is presented with soft blue walls and modern lighting. A cozy couch is positioned near large windows, while a kitchen featuring white cabinetry is visible in the background. Natural light enhances the airy feel of the space.

Guest suite in Essex

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.

4.97 out of 5 average rating, 215 reviews

The farmhouse, constructed in 1856, is showcased with its classic white exterior and black accents. Large windows allow natural light to fill the space, while lush greenery surrounds the property. A pebble pathway leads to the entrance, enhancing the inviting atmosphere.

Home in Old Lyme

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

4.92 out of 5 average rating, 228 reviews

A two-story beach house is presented, featuring light grey shingles and a welcoming blue front door. The landscaped yard includes green shrubs and colorful flowers. A separate structure is visible in the background, offering additional space. Clear skies and trees are seen above.

Townhouse in Westbrook

Wake up with views of the ocean

Located in sleepy Westbrook, Ct and across the street from Long Island Sound, this beach house is spacious with a full kitchen, dining, and living room. A large back yard for children to play and parents to barbeque is included.

A wooden pathway leads through sandy terrain, flanked by low vegetation. The scene is set against a clear blue sky, creating a serene atmosphere that guides visitors toward the shoreline.

4.86 out of 5 average rating, 243 reviews

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 spot.

Popular amenities for Westbrook holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Westbrook

4.96 out of 5 average rating, 46 reviews

A cozy living area is presented with a neutral color palette. A comfortable sofa is draped with a textured throw, and an organic wooden coffee table is centered within the space. Art prints adorn the walls, while natural light gently illuminates the room.

Flat in Westbrook

Meadowview & Pondside Retreat

A single-story coastal home is showcased, featuring a light gray exterior and large windows. Outdoor seating is available on the patio beneath a purple umbrella, and a white stone border outlines the property. An American flag is visible, fluttering in the breeze.

4.8 out of 5 average rating, 41 reviews

Cozy Westbrook Vacation Rental - Walk to Beach!

An aerial view captures the expansive sandy beach stretching along the coastline, adjacent to serene waters reflecting sunlight. Houses line the shore, with some beach chairs positioned near the water's edge, creating a peaceful coastal scene.

4.98 out of 5 average rating, 48 reviews

Barnacle Bay Beach House

5 out of 5 average rating, 5 reviews

Home in Clinton

Historic Coastal Home • Marsh Views • Pet-Friendly

5 out of 5 average rating, 53 reviews

The exterior of a bright red caboose is captured against a backdrop of tall trees. Sunlight filters through branches, highlighting the unique structure. A pathway of gravel leads to the entrance, which features steps and a small platform. The inviting colors complement the natural surroundings.

Guest house in Brooklyn

Historic Railroad Caboose - Unique CT Farm Escape

4.95 out of 5 average rating, 22 reviews

The renovated stone house is set against a lush green forest. Vibrant orange flowers bloom in the foreground, while towering trees surround the property. The house features a combination of stone and modern elements, with large windows that blend with the natural environment.

Guest house in Clinton

Clinton's Hidden Secret, A Distillerie until 1926