Beach house holiday rentals in Old Saybrook

#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!

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Niantic River Beach Cottage | Waterviews

Kick back and relax in this quiet, stylish New England beach cottage with water views, a private neighborhood beach, an outdoor shower, and a sunny patio for coffee or evening wine. Just minutes from downtown Niantic, you’ll find beaches, cafés, bakeries, ice-cream stands, seafood, boutiques, boat launches, trails, outdoor concerts, and more—all within a short drive or bike ride. Perfect for a romantic getaway, a family weekend, or some quiet coastal downtime. See why guests love staying here!

Thames River Retreat · CT College+Casinos+USCGA

This home on the Thames River is the ultimate getaway for a family seeking relaxation and outdoor adventures. With five bedrooms, three and a half bathrooms, a spacious kitchen, and a comfortable living room with stunning views of the water and private beach. The master bedroom with on suite bathroom, large deck overlooking the river, with direct access to the backyard where you can lounge on the private beach, play lawn games, or take a dip in the river. We have 2 kayaks available for use.

Seas the Day at the CT Shoreline

Welcome to a slice of heaven by the water. Spacious 4BR updated beach cottage. Well-equipped kitchen, outdoor shower & gas grill. Sunny enclosed porches downstairs & upstairs. 2 decks for friends & family to stretch out while dining al fresco or simply lounging. 5 minute walk to 2 private beaches & 3 miles to 2 town beaches & the center for unique shops & eateries. Plus... fiber optic wifi, free coffee bar, games, bikes, beach toys, beach wagon & umbrellas. Spas, outlets & casinos nearby.

Beachfront Paradise

Beautiful beachfront home available weekly in season (6/20/26-9/5/26) 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.

Addison's Oasis

Welcome to Addison's Oasis! This charming beachfront cottage is located in Old Saybrook, CT. This adorable cottage is the quintessential New England coastal escape. With sweeping views of LI Sound and direct access to a family friendly private beach, it's a favorite spot to all where sunrises are magical and summer feels endless. This sweet recently renovated seaside cottage captures everything that makes OS so special- historic charm and that unmistakable coastal New England magic.

“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!

Duckling Crossing | Beach House on the Sand

This amazing beachfront home has one of the best private beaches in southeastern Connecticut. The sand is terrific, it squishes between your toes and feels soft and conforming with every step! Seldom crowded by the few who share beach rights the views are amazing and less than 1 mile away you have a perfect view of Duck Island. Once you pull yourself away from the beach you are sure to fall in love with this amazing home. With 4 bedrooms and 2 full baths, it easily accommodates 9 guests

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

INSTANT BOOK: June 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Waterfront 10 min to Uconn - fire pit outdoor tv

🌊 Lakefront Amenities at Panorama 🏖 Direct Waterfront on Coventry Lake 🚤 Private Dock Access 🏝 45’ Private Sandy Beach 🔥 Gas Fire Pit (yard) 🔥 Gas Fire Table (deck) 📺 Outdoor TV for lakefront movie nights 🍔 Grill for cookouts 🛶 Canoe 🏄‍♀️ Stand-Up Paddleboard 🚲🌊 Hydrobikes ☀️ Open Floor Plan with Lake Views 📺 TVs in Every Bedroom ☕ Coffee Bar with Complimentary Nespresso Pods, Teas & Coffee 🧺 Laundry On-Site

Eastern Point 4 Season Ranch

Located in beautiful Eastern Point neighborhood this fully renovated 3 bedroom ranch home is pet friendly and has 1 1/2 baths, a very comfortable living area, a full working kitchen with pots pans and utensils, deck off the kitchen, large open back yard, and a fire pit. If you’re a military, EB, or health care contractor looking for a longer term rental we have discounted pricing available. Message me for any questions.