Beachfront holiday rentals in Westbrook

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Top-rated beachfront rentals in Westbrook

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Superhost

Apartment in North Fork

4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Top guest favourite

Flat in Milford

4.97 out of 5 average rating, 576 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Guest favourite

Apartment in North Fork

4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Top guest favourite

Flat in Westbrook

5 out of 5 average rating, 7 reviews

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.

Guest favourite

Home in Milford

4.96 out of 5 average rating, 222 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Guest favourite

Home in Stonington

4.97 out of 5 average rating, 104 reviews

Mystic Harbor House · walk Downtown-Train/Aquarium

Perfect for a family vacation or a couples' getaway. Experience the charm and beauty of Mystic at The Mystic Harbor House. This stunning 3-bedroom home boasts breathtaking water views of the Mystic Harbor and Mason's Island. Take a short 4-minute walk to the Mystic Amtrak train station or a 7–10-minute stroll to the historic downtown area or a 6-minute drive to the Mystic Aquarium. Wake up to the refreshing ocean breeze as you sip your morning coffee and take in the tranquil surroundings.

Guest favourite

Home in Niantic

4.96 out of 5 average rating, 192 reviews

Beachfront Paradise

Beautiful beachfront home available weekly in season (6/21/25-9/6/25) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, movie theatre, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Guest favourite

Home in Westbrook

4.96 out of 5 average rating, 25 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!

Top guest favourite

Home in Branford

4.98 out of 5 average rating, 155 reviews

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Top guest favourite

Home in Westbrook

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.

Guest favourite

Cottage in Chester

4.97 out of 5 average rating, 273 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Top guest favourite

Guest suite in Westbrook

4.97 out of 5 average rating, 72 reviews

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!