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Vacation rentals in Westbrook

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Top-rated vacation rentals in Westbrook

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

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Guest favorite
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 favorite
A riverfront deck is furnished with two lounge chairs and a glass table, surrounded by lush greenery and trees. The view overlooks a calm stretch of the Patchogue River, creating a serene environment for relaxation and enjoyment of nature.
Cottage in Westbrook
4.87 out of 5 average rating, 215 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Superhost
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, 103 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.

Guest favorite
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, 104 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 favorite
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

Beautiful View 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.

Superhost
A charming home exterior is lined with vibrant green ivy, surrounded by a lush garden area. A gravel pathway leads to the entrance, and cozy seating arrangements are visible in front of the house. Large windows allow natural light to fill the interior.
Cottage in Old Saybrook
4.78 out of 5 average rating, 106 reviews

Storybook 2 Bedroom Cottage

Enjoy a relaxing stay at this charming storybook home which has just been refreshed professionally and redesigned with unique and gorgeous antique furnishings and decor. Built in 1895, the home was re-envisioned by designer Charles Spada in the 90’s. A lovely private back yard with beautiful stone work and plantings. The proximity to shopping, galleries, restaurants and Old Saybrook, Town Beach and Katherine Hepburn theater makes this location ideal.

Top guest favorite
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
4.74 out of 5 average rating, 248 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.

Top guest favorite
A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.
Home in Old Saybrook
4.92 out of 5 average rating, 106 reviews

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Top guest favorite
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, 90 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 favorite
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, 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!

Top guest favorite
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, 127 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 favorite
The exterior of a two-story building is depicted, featuring natural wood siding and multiple windows. A gravel path leads to a covered entrance surrounded by benches and flower planters. Large trees provide shade, enhancing the serene atmosphere of the setting.
Loft in Essex
4.94 out of 5 average rating, 463 reviews

Unique apartment in former art gallery.

A private apartment in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. A spacious and open floor plan offers a peaceful stay along with thoughtful touches with your comfort in mind.

Popular amenities for Westbrook vacation rentals

When is the best time to visit Westbrook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR4,078 ZARR4,144 ZARR4,062 ZARR4,078 ZARR4,568 ZARR4,633 ZARR5,204 ZARR5,710 ZARR4,976 ZARR4,486 ZARR4,486 ZARR4,551 ZAR
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.

Quick stats about vacation rentals in Westbrook

  • Total vacation rentals

    Explore 150 vacation rentals in Westbrook

  • Nightly prices starting at

    Westbrook vacation rentals start at R979 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 4,480 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Westbrook vacation rentals include wi-fi 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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