Vacation rentals in Westbrook

5 out of 5 average rating, 63 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.

4.89 out of 5 average rating, 161 reviews

Cottage in Westbrook

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.

4.79 out of 5 average rating, 125 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

4.95 out of 5 average rating, 38 reviews

Guesthouse in Clinton

Studio Cottage

Peaceful & centrally located studio cottage on Connecticut shoreline. Close to beaches, restaurants, winery, outlet shopping, and I-95. Approximately 20 minutes outside of New Haven. Ideal for exploring the shoreline & river valley. Bright, clean, efficient, well- equipped cozy studio cottage with queen bed, sitting area, kitchen & full bathroom . Outdoor space with fire pit & grill. Onsite parking. Ideal for two people whether traveling through the area or for a little rest & relaxation

5 out of 5 average rating, 7 reviews

Apartment in Westbrook

Private Guest Suite Water Views

This cozy fully equipped guest suite boasts scenic water and marina views in the center of the Westbook Marine area. This charming retreat offers an escape from the hustle of everyday life. Ocean breeze and views from upper private covered porch. Bring your bikes enjoy scenic shore rides. One queen bed, full bath and fully equip kitchen, cozy living and dining area. Roku ready, AC and Wifi. Free parking. Rent kayaks across the street. Restaurants in all directions. Casino's 30 min.

4.96 out of 5 average rating, 26 reviews

Barnacle Bay Beach House

Welcome to Barnacle Bay Beach House, in Westbrook, CT! A cozy 3BR, 2BA home just a short trip from the beach. Enjoy a fully-equipped kitchen, comfortable living area with a TV, and serene bedrooms. Features include Wi-Fi, a kitchen fit for a chef, and tons of updates throughout. Perfect for a family getaway or a beachside retreat! Barnacle Bay is more than just a place to stay - it's a place to create lasting memories. Book your stay now and experience the magic of coastal Connecticut!

4.97 out of 5 average rating, 193 reviews

Home in Clinton

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

5 out of 5 average rating, 25 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.

4.96 out of 5 average rating, 27 reviews

Apartment in Westbrook

Meadowview & Pondside Retreat

We welcome you to a serene and peaceful getaway at our recently renovated apartment. Explore 88-acres of woods, New England rock walls, streams, meadow and pond all without leaving our beautiful native landscape. We are conveniently located within a 10 minute ride from I95/Rt.9, the quaint villages of Chester, Deep River & Essex or down to the CT shoreline. We are also a working herb farm and happy to arrange farm tours, medicine making classes, or plant walks/guided hikes.

4.97 out of 5 average rating, 72 reviews

Guest suite in Westbrook

King Bed, Walk to Beach, Kitchenette, Porch/Patio

Discover why guests are raving about our private guest suite in coastal Westbrook, CT! Thoughtfully designed for comfort and convenience, it’s an ideal retreat for those seeking a seamless, relaxing travel experience. Perfect for solo travelers or couples, the suite combines contemporary design with thoughtful amenities for an unforgettable stay. Guests love the proximity to the beach, fine dining, and local attractions!

Guest suite in Old Saybrook

5 out of 5 average rating, 82 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!

4.96 out of 5 average rating, 110 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

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Apartments

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Cottages

Quaint homes, peaceful surroundings

Popular amenities for Westbrook vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Westbrook

4.77 out of 5 average rating, 26 reviews

Adorable Cottage with porch, walk to water & town

CaseyRating, 5 stars1 month ago

Very quiet, good location, close to outlets, beach etc.

5 out of 5 average rating, 5 reviews

Guest suite in Clinton

Private 2-room suite + bath in beach town

LizzieRating, 5 stars2 weeks ago

We had a great time! The unit is very clean and comfortable and has everything you would need. The unit is exactly as pictured and described. The outdoor amenities (hot tub, deck and grill) are a huge bonus. The outdoor space is so calm and serene. The neighborhood is very quiet and peaceful and there are plenty of food/dining options within driving distance in lieu of a full kitchen (which is already described). Delicious lobster rolls are only a few minutes away via car which is great! While we were there we visited Lake Compounce as well as the USS Nautilus - that was fun! Suzanne is such a kind and wonderful host. She made our stay extra pleasant and was always available to answer questions or provide anything necessary. She provided a snack basket which came in handy and was much appreciated. Her dog,Molly, is a sweet dog and we enjoyed her company. We are so grateful for Suzanne and her warm hospitality :) Thank you once again!

5 out of 5 average rating, 12 reviews

Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

TimothyRating, 5 stars1 month ago

We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

4.89 out of 5 average rating, 74 reviews

Condo in Old Saybrook

Seashore getaway - CT shoreline

RussellRating, 5 stars2 weeks ago

Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.

4.99 out of 5 average rating, 69 reviews

Apartment in Clinton

Cozy Shoreline Getaway

HowardRating, 5 stars1 month ago

Second time staying at this Airbnb. Excellent hosts, conveniently located, and cottage had all the amenities.

4.83 out of 5 average rating, 12 reviews

Cottage in Westbrook

Oceanside home steps to private beach!

EmmaRating, 5 stars11 months ago

Spent the weekend here for my husband’s birthday with our kids. They loved the big private beach. Almost no one else was on it. We needed an air mattress for our daughter and they quickly brought one over. The place was STOCKED with everything you could need!

4.55 out of 5 average rating, 22 reviews

Cottage in Westbrook

Remodeled Cottage Private Old Kelsey Point Beach

LuanneRating, 5 stars8 months ago

Had a great stay. Very comfortable and well equipped. Close to shopping, restaurants, and a quick and easy walk to a private beach! Definitely want to stay again next year.