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Holiday houses in Westbrook

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Quick stats about holiday rentals in Westbrook

  • Total holiday rentals

    Explore 160 holiday rentals in Westbrook

  • Nightly prices starting at

    Westbrook holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,740 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    160 of Westbrook holiday rentals include Wi-Fi access

  • Popular amenities for guests

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

  • 4.8 Average rating

    Westbrook stays are highly rated by guests—averaging 4.8 out of 5!

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
4.87 out of 5 average rating, 54 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.

ValueLocationLaundry

Top Guest favourite
A newly remodeled home is set amidst a lush green lawn, featuring a spacious front porch with blue Adirondack chairs. The exterior is characterized by a blend of gray siding and a welcoming entryway, surrounded by a well-maintained garden and a wooden sign.
Home in Westbrook
4.97 out of 5 average rating, 30 reviews

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.

FamilyLocationAccuracy

Top Guest favourite
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.
Home in Westbrook
4.99 out of 5 average rating, 86 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.

LocationFamilyBackyard

Superhost
A contemporary living area features a spacious, dark sectional sofa paired with a wooden coffee table. A textured area rug lies on the floor, while large windows allow natural light to illuminate the space. Artwork is displayed on the walls, enhancing the modern decor.
Apartment in Westbrook
4.78 out of 5 average rating, 65 reviews

Shoreline postmodern apartment

Brand New Construction- Everything shiny and new! Located in the heart of the marine district, and 2 miles from Waters Edge Resort. This 2 bedroom apartment with pull out couch for a third bed offers postmodern styling, and a wide open floor plan. Just steps from all of the major restaurants, bars, breweries, and beaches in Westbrook ct. Brand new and high end finishes, offers easy access to 1-95, all of the local marinas, and places: Lenny & Joes Fish, Bill's Seafood, & Westbrook Lobster co.

LocationFamilyIndoor spaces

Superhost
The exterior of a two-story blue house is shown, featuring a sloped roof and white accents. A wooden deck with blue chairs offers a welcoming space. Simple landscaping includes gravel and grass, providing easy access to the entrance and surrounding areas.
Townhouse in Westbrook
4.93 out of 5 average rating, 27 reviews

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.

LocationFamilyCleanliness

Guest favourite
A wooden dock stretches over the calm waters, supported by several sturdy posts featuring black caps. The sky above is clear with soft clouds, enhancing the serene coastal atmosphere.
Home in Old Saybrook
4.92 out of 5 average rating, 104 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

LocationFamilyComfort

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
4.91 out of 5 average rating, 108 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

FamilyLocationNearby

Top Guest favourite
The exterior of the cottage is characterized by a charming stone chimney and a vibrant green door. The white siding contrasts with lush greenery, while a small seating area features two colorful chairs on the well-maintained lawn. A stone pathway leads toward the entrance.
Cottage in East Haddam
5.0 out of 5 average rating, 108 reviews

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

FamilyLocationComfort

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
4.98 out of 5 average rating, 81 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.

LocationFamilyAccuracy

Top Guest favourite
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
4.75 out of 5 average rating, 254 reviews

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.

FamilyValueLong stay

Superhost
Home in Old Saybrook
5.0 out of 5 average rating, 4 reviews

Cozy beach side home Chalker Beach Old Saybrook

Relax and unwind in this beautifully renovated 3-bedroom, 2-bath beach house, just a 2-minute walk to Chalker Beach in Old Saybrook. Enjoy a fully updated interior, a private backyard perfect for relaxing or dining outdoors, and parking for up to 3 vehicles. Ideal for families, couples, or friends looking to experience the Connecticut shoreline with comfort, convenience, and easy beach access.

FamilyLocationHospitality

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 Old Saybrook
4.98 out of 5 average rating, 110 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!

FamilyLocationSleep quality

Popular amenities for Westbrook holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Westbrook's top sights

Essex Steam Train & Riverboat

168 locals recommend

Ivoryton Playhouse

42 locals recommend

Clinton Town Beach

23 locals recommend

Westbrook Outlets

21 locals recommend

Stewart B. McKinney National Wildlife Refuge

12 locals recommend

Action Sports

8 locals recommend

Other great holiday rentals in Westbrook

Guest favourite
Home in Old Saybrook
5.0 out of 5 average rating, 9 reviews

Bird Bliss. Our Waterview home &deep water dock.

FamilyLocationWalkability

Superhost
Apartment in Westbrook
4.76 out of 5 average rating, 17 reviews

Coastal Westbrook Loft Vaulted Ceilings & Lvl 2 EV

LocationFamilyQuiet

Top Guest favourite
Home in Westbrook
4.98 out of 5 average rating, 59 reviews

Secret Seaside Stone Cottage

FamilyValueCleanliness

Top Guest favourite
Home in Clinton
4.95 out of 5 average rating, 22 reviews

The Connecticut Cottage | Historic Modern Charm

ValueLocationBeach

Top Guest favourite
A modern kitchen is shown, featuring gray cabinetry and a spacious island that seats two. Appliances, including a stove and refrigerator, are neatly arranged, and a window allows natural light to enter the room. Shelving displays dishes and kitchen essentials.
Home in Westbrook
5.0 out of 5 average rating, 23 reviews

SunsetSkies 1stFl | filmed 4 TV+walk 2 Water’sEdge

FamilyLocationTV

Top Guest favourite
A charming cottage with a white exterior is presented, featuring a spacious front porch and decorative railings. A basketball hoop stands prominently on the gravel driveway, with planters and shrubbery visible in the foreground. Clear blue skies enhance the inviting appearance of the home.
Cottage in Westbrook
4.99 out of 5 average rating, 88 reviews

Beautiful Updated Cottage walk to the Beach

FamilyValueQuiet

Top Guest favourite
Home in Old Saybrook
4.96 out of 5 average rating, 23 reviews

The Saybrook Point Bungalow, Stroll to Downtown

LocationFamilyAccuracy

Guest favourite
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.
Home in Westbrook
4.97 out of 5 average rating, 30 reviews

Beachside Bliss w/ Game Room, Gym & Golf Green

LocationValueWalkability

When is the best time to visit Westbrook?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$425 NZD$431 NZD$423 NZD$455 NZD$510 NZD$511 NZD$542 NZD$595 NZD$518 NZD$467 NZD$467 NZD$474 NZD
Avg. temp0°C1°C4°C10°C16°C21°C24°C24°C20°C14°C8°C3°C

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.

Destinations to explore