
Beachfront vacation rentals in Westport
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Top-rated beachfront rentals in Westport
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

#2 Milford Beach (across street) Charles Isle 2BR
Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Steps to Beach-Water View-Pet Friendly-Fenced Yard
The Black Pearl is Milford's most luxurious high-end beach bungalow! Just a few steps to Wildemere Beach with water views. Walking distance to the Tyde wedding venue. Pet friendly with a fully-fenced backyard, firepit, deck, & outdoor shower. Thoughtful, modern beach design with 3 bedrooms and 2 full bathrooms. King primary bedroom with private en-suite bath. Fully stocked kitchen. Laundry for guest use. Huge TV & wifi. Central air. Book The Black Pearl & explore Milford on your next vacation!

Waterfront Beach Cottage in Connecticut
Our lovely cottage is as beautiful and peaceful as the photos. With gorgeous water views, it's a wonderful place to relax, walk on the beach, cook dinner and drink wine while watching the sun set. It's cozy and unforgettable, just 90 minutes from Grand Central on Metro North. First bedroom has a queen-size bed, and the second bedroom has a full-size bed. An extra-long twin in a quiet corner of the living area is both a daybed and extra accommodation. The bathroom has a shower and claw foot tub.

waterfront on Lake Zoar[ SUITE]
Enjoy your private patio overlooking the lake, Or just walk 12 steps to water Edge and visit the cozy lower level and enjoy the swings . Use our kayaks, and don’t forget to bring your fishing pole, go swimming ,or just sit in the sun with a book and listen to the waterfall and you are welcome to sit by the firepit Optional boat dock space, parking Hosts live upstairs Two miles to quaint Sandy Hook center with grocery and restaurants All quests must be register Ninety minutes to Boston/nyc

Beach Haven - waterfront, near Yale, sunsets
Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

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!

“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!

Cheerful 3 Bedroom Cottage with Fire Place
There is still time to book for some summer dates at the beach. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Charming Fairfield Beach Cottage
Escape to our newly renovated waterfront cottage in Fairfield, just steps from a private beach on the Long Island Sound. This charming retreat is perfect for families and couples, offering a modern kitchen, private deck, and high-speed WiFi. Unique perk: Enjoy complimentary 24/7 access to a beautiful co-working space just 3 miles away. A perfect blend of relaxation and productivity awaits!

Beachfront house on Long Island Sound
Fully furnished house with a private beach overlooking Long Island Sound waters in a quiet residential area. Enjoy the beach, kayaking , and nearby nature sanctuary. Excellent Greek Spot Cafe & Grill, just a 3-minute walk from the house. Discover many more cafes, restaurants, and bars, as well as great shopping attractions, just a short drive away.

Seabreeze at the beach, West beach Stamford Ct
3 bedroom 4 beds at the beach , free parking also free access to the beach, comes with cart, chairs, towels and umbrella , 3 adult bicycles and boogie boards. close to downtown and Harbor point, great for people coming to work in stamford. about 5 minutes to route 95. also a nice little Irish Pub as you enter the beach. "GREAT FOOD AND DRINKS"

Beautiful Waterfront Cottage
This is a modern new renovated water front Cottage! Private access to exclusive Bayville beach! The unit has a king size bed. A loft with Japanese style Tatami could sleep two kids. Beautiful bathroom with high tech toilet. Washer and dryer. Have fun with the whole family at this stylish place.
Popular amenities for Westport beachfront rentals
Pet-friendly beachfront home rentals

Milford Beach House - Newer Construction!

Cottage in Calverton

Beautiful Beach and Downtown Combo

Bohemian Beach Oasis- Private Beach

Beach Escape-Summer Rental Steps to Beach

Mid Week Specials! - Beachfront, Dog Friendly

The Surf Shack

Low Tide
Private beachfront home rentals

Newly Built Beach House Getaway

Salty Kisses Beach Cottage Milford CT

A BREATHTAKING AND RELAXING PLACE TO CALL HOME

Waterfront Beach Cottage

Cheerful 2 bedroom cottage on beach

Beach House steps from sand & Amazing Views

Steps to the Beach. Lovely 2-Bedroom apt

Connecticut Beach Cottage on The Long Island Sound
Luxury beachfront home rentals

Beautiful, Spacious, Waterfront Home on the Bay

Beach house - Sapphire Sandbar

Hang by the (Chel)SEA

House of the Rising Sun!

Beach House on LI Sound Waterfront

Breathtaking Panoramic Waterfront

Glen Laurel on the Sound (w/private beach)

Sand & Salt Waterfront Home on a Private Beach
Quick stats about beachfront rentals in Westport

Nightly prices starting at
Westport vacation rentals start at $629 CAD per night before taxes and fees

Verified guest reviews
Over 50 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westport rentals

4.9 Average rating
Westport stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a fireplace Westport
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- House rentals Westport
- Rentals with a washer and dryer Westport
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- Rentals with a firepit Westport
- Beachfront rentals Connecticut
- Beachfront rentals United States
- Times Square
- Madison Square Garden
- New York City Center
- New York University
- Central Park Zoo
- Columbia University
- MetLife Stadium
- Yale University
- Yankee Stadium
- United Nations Headquarters
- Jones Beach
- Rockefeller Center
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- Empire State Building
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- Statue of Liberty
- Radio City Music Hall
- Brooklyn Bridge
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- Thunder Ridge Ski Area
- The Metropolitan Museum of Art
- Astoria Park



