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Holiday rentals in Westbrook

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Top-rated holiday rentals in Westbrook

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A serene beach shoreline is depicted, featuring soft sand leading gently to calm waters. The clear blue sky meets the horizon, creating an expansive view. Footprints are visible in the sand, illustrating a sense of tranquility and solitude by the sea.
Bungalow in Westbrook
4.84 out of 5 average rating, 44 reviews

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.

Guest favourite
A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.
Home in Westbrook
4.8 out of 5 average rating, 139 reviews

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Guest favourite
A two-story beach cottage is presented with a light exterior and a spacious balcony. Large sliding glass doors are visible at the lower level, providing easy access to the outdoor space. Nearby, a driveway is seen leading towards the garage.
Cottage in Westbrook
4.9 out of 5 average rating, 101 reviews

A Beach House Gem

Beautiful beach cottage with a private beach. Sleeps up to 6 comfortably with two full beds and 1 queen in the master. with a beautiful balcony Full bath upstairs,1/2 off the kitchen entrance outside key on the key chain The main living area has a TV, air conditioning, and sliding doors to a deck. The updated kitchen has a dishwasher, microwave, cooktop, oven, and coffee maker. There are 2 parking spots in front of the garage The house is not winterized there are no bookings from Nov1

Top guest favourite
Home in Westbrook
5 out of 5 average rating, 52 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.

Top guest favourite
A welcoming view of Belle Vue Cottage features a well-kept lawn with a sign indicating its name. The cottage is framed by trees, with a driveway leading to it. A garage is visible in the background, contributing to the serene atmosphere of the neighborhood.
Cottage in Old Saybrook
4.99 out of 5 average rating, 152 reviews

Belle Vue Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Top guest favourite
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.
Home in Westbrook
4.97 out of 5 average rating, 72 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.

Top guest favourite
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.
Home in Westbrook
4.94 out of 5 average rating, 79 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!

Top guest favourite
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
4.94 out of 5 average rating, 89 reviews

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.

Top guest favourite
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.
Guest suite in Saybrook Manor
4.98 out of 5 average rating, 108 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!

Guest favourite
Tiny home in East Lyme
4.98 out of 5 average rating, 146 reviews

Lakeside Serenity Tiny House

Embrace Lakeside Serenity Unwind in our cozy tiny home at The Island RV Park, right on Pattagansett Lake. A retreat for relaxation, with a queen bed, full amenities, and fast Wi-Fi. Perfect for romantic escapes or peaceful solo retreats. Help yourself to our shared kayaks and watercraft (available May - Oct) to get out on the water!

Top guest favourite
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
4.97 out of 5 average rating, 126 reviews

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.

Top guest favourite
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
4.92 out of 5 average rating, 230 reviews

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.

Popular amenities for Westbrook holiday rentals

When is the best time to visit Westbrook?

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Avg. price$317 SGD$322 SGD$316 SGD$317 SGD$355 SGD$360 SGD$404 SGD$443 SGD$386 SGD$348 SGD$348 SGD$354 SGD
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Frequently Asked Questions

  • What are the best places to stay in Westbrook?

    Vacation rentals near the waterfront, cozy cottages, and locally owned inns in quieter neighborhoods are frequently suggested places to stay. Many options provide easy access to both beaches and shops.

  • What are the best things to do in Westbrook with kids?

    Families can enjoy building sandcastles at Westbrook’s beaches, exploring community playgrounds, or boating near local marinas. Nature preserves with easy trails are frequently suggested for low-key outdoor adventures.

  • What are some of the best things to do in Westbrook?

    You can explore sandy beaches, visit local marinas, or browse unique shops around town. Westbrook has art galleries and nature preserves that are often recommended for a relaxing outing.

  • How is the weather in Westbrook?

    Westbrook has cold, snowy winters between 24–38°F (–4–4°C) and warm summers with highs near 82°F (28°C). Spring and fall bring mild temperatures and occasional rain, so layers and a light rain jacket are useful.

  • When is the best time to visit Westbrook?

    Late spring through early fall is often recommended for milder weather and outdoor activities, with many visitors enjoying the beaches and nature trails during these seasons. Cooler months are quieter and appeal to those seeking a peaceful getaway.

  • What are the best places to visit in Westbrook?

    The town beach, marinas, and nature preserves are among the most popular places to visit in Westbrook. Art galleries and quaint shops add local character, especially around the town center.

  • What are some hiking trails in Westbrook?

    You can explore easy walking paths in local nature preserves and coastal marshes around Westbrook. Trails often feature viewpoints, boardwalks, and opportunities to spot native wildlife.

  • What are some family activities we can do in Westbrook?

    Families often explore the beaches, visit marinas for boat watching, or participate in arts and crafts events around the community. Nature preserves and local playgrounds are also welcoming spots for all ages.

  • What are some of the best day trip ideas from Westbrook?

    You can explore neighboring coastal towns, visit local vineyards, or stroll through historic villages around the region. Wildlife refuges, state parks, and maritime museums are also popular choices for a varied outing.

  • Are there any pet friendly accommodations available in Westbrook?

    Many vacation rentals and some local inns in Westbrook welcome pets, especially near the beach or quieter neighborhoods. Always confirm policies for pets before booking your stay.

  • What are some local tips for visiting Westbrook?

    Locals often suggest bringing layers for changing weather and exploring markets for fresh seafood. Early mornings at the beach or nature reserves tend to be quieter, and many small shops have a relaxed, welcoming pace.

  • What is Westbrook known for?

    Westbrook is known for its sandy beaches, vibrant marinas, and a tradition of fresh seafood. The town has scenic nature preserves and a welcoming small-town atmosphere that draws visitors seeking coastal charm.

  • What are the best hidden gems to explore in Westbrook?

    Tucked-away art studios, small nature trails, and locally run ice cream shops invite a more personal look at Westbrook. Visiting local markets or lesser-known beaches can reveal a quieter side of this coastal town.

  • What are the best foods to try in Westbrook?

    Westbrook has seafood-focused menus featuring dishes like lobster rolls, clam chowder, and fried oysters. Locally made ice cream and New England–style pizza are also frequently suggested treats.

  • What should I bring for a trip to Westbrook?

    Pack casual clothes, layers for cooler evenings, and a light jacket, especially in spring or fall. Comfortable shoes, sunscreen, and rain gear can help you enjoy both beaches and nature trails around Westbrook.

  • What is the nightlife in Westbrook like?

    Nightlife in Westbrook is relaxed, with local pubs, casual music venues, and waterfront restaurants providing a laid-back scene. Many spots feature live performances or community events, especially in warmer months.

  • What are the most popular events or festivals in Westbrook?

    Westbrook hosts summer concerts on the green, craft fairs, and seasonal celebrations around Memorial Day and Independence Day weekends. Community festivals featuring local food and music are frequently suggested by residents.

  • Are there family friendly vacation rentals in Westbrook?

    Westbrook has a variety of family-friendly vacation rentals, including cottages and homes with multiple bedrooms or equipped kitchens. Many options are located near beaches, parks, or quiet neighborhood settings.

Quick stats about holiday rentals in Westbrook

  • Total holiday rentals

    Explore 150 holiday rentals in Westbrook

  • Nightly prices starting at

    Westbrook holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,480 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    150 of Westbrook holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Westbrook rentals

  • 4.9 Average rating

    Westbrook stays are highly rated by guests – averaging 4.9 out of 5!

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