Beachfront holiday rentals in Westport

#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!

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.

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. 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.

Beach House with Private Beach

Welcome to Baby Blue on the Creek, a stunning renovated coastal retreat with private beach access! Nestled on the peaceful creek side of Fairfield Beach Road, this fully newly furnished getaway offers an open-concept kitchen, a cozy living room, and a covered deck with breathtaking water views. The primary suite boasts a marble bath, plus two more bedrooms. The top floor features a bonus room with two beds, laundry, and rooftop deck. Relax by the water and enjoy the best of beachfront living!

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!

Ocean View Cottage: Yale, Beach, Wedding & Golf

The Island Sound Cottage is pet friendly, has been newly renovated (not a shared space). 15 mins to Yale & Downtown; unobstructed ocean view from the living room & balcony. Located in a beautiful and safe location. This pristine home comes with breathtaking ocean views! Head out your front door to stroll along the famous Pardee Seawall Park on The Long Island Sound. Enjoy this colonial cottage with big windows, skylights, balcony, plenty of sunlight and sunset. *Fully enclosed backyard.

Cozy 3BR Stay in Stamford & Near Old Greenwich

Comfortable 3-bedroom apartment in a quiet Stamford neighborhood, located behind the beautiful Innis Arden Golf Club and close to Wings Arena. Each bedroom features a queen bed, bedside table with charging station, and lamp. The master bedroom includes a TV and a small workspace. The home also offers a brand new kitchen with ample cabinet space and an in-unit washer and dryer. Guests enjoy a convenient location near Old Greenwich, downtown Stamford, beach parks, and the train station.

Steps to Beach - Direct Water View - Pet Friendly

The Black Pearl is Milford's most luxurious high-end beach bungalow! A few steps to Wildemere Beach with a year round water view. Pet friendly with a fully-fenced backyard, firepit, deck, & outdoor shower. 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. 75" Smart TV & wifi. Central Air with Nest thermostat. Book The Black Pearl & explore Milford on your next vacation!

Bohemian Beach Oasis- Private Beach

Designer beach house 120 steps to private beach on Merwin Avenue! Embrace the Bohemian life & escape w/ friends & family. Enjoy the spacious kitchen w/ granite counters & patio access. Bedrooms include a spectacular master suite offering a spa bathroom & 2 more bright rooms upstairs. The third-floor bonus room leads out to a rooftop deck w/ water views! Charming Tiki hut & BBQ for entertaining. Please reach out and schedule your special stay at the Bohemian Beach Oasis.

A BREATHTAKING AND RELAXING PLACE TO CALL HOME

NEWLY RENOVATED- NEW FLOORING, COVERED PATIO DECK-AWNING & ADIRONACKS, SPECTACULAR SUNRISE/SUNSET, MANICURED YARD, 1 BLOCK CEDAR SANDY BEACH, WASHER/DRYER ON PREMISES, FIBER OPTIC WIFI, TV EQUIPPED-ROKU-AMAZON PRIME VIDEO A PLUS FOR YOUR ENJOYMENT, CONNECTICUT AUDOBON SOCIETY, CONVENIENT AND EASILY ACCESSIBLE TO DOWNTOWN MILFORD CENTER- RESTAURANTS, SHOPS, ENTERTAINMENT, WESTFIELD MALL, METRO TRAIN STATION, I-95 & BOSTON POST ROAD, NOT SUITABLE FOR PETS PLEASE

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!