House holiday rentals in Old Saybrook

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Top-rated house rentals in Old Saybrook

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Old Saybrook
5 out of 5 average rating, 25 reviews

Sunrise Beach Cottage

Our newly renovated home is steps away from Cornfield Point’s many private Beaches, tennis court, boardwalk and Sandbar. With Multiple Water views, 4 private beaches, new appliances, grill, furniture, washer dryer, beds, patio, fire pit, golf, kayaking, pickle ball , tennis, playground, clubhouse, The Kate , Casino’s , 3 lighthouses, private boat ramp. We will try to accommodate your dog too. Sat - Sat 7 night stays, other by request. Sunrises, Sunsets & Sea Breezes Academic Renters 2025

Top guest favourite
A charming cottage is depicted with a shingle exterior, a welcoming front porch, and a chimney. The grassy landscape is flanked by flowering shrubs, and a path leads to the entrance. A red barn is visible in the background, enhancing the rural setting.
Home in Waterford
4.99 out of 5 average rating, 136 reviews

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!

Guest favourite
A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.
Home in Columbia
4.91 out of 5 average rating, 112 reviews

Breathtaking home with unforgettable views & pool!

This perfect peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or star gazing at night. far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. please let us know before booking more than 4 people whether it is just for the day or night or both. no loud music no parties

Top guest favourite
A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.
Home in Saybrook Manor
4.96 out of 5 average rating, 134 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Guest favourite
A spacious deck overlooks calm waters, with a view of boats and distant shoreline. The wooden surface provides ample space for relaxation, while white railings frame the serene scene. Soft clouds drift across the sky, reflecting in the water's surface.
Home in Groton
4.95 out of 5 average rating, 212 reviews

True Ocean Front Vacationing - Groton/Mystic

Bright and airy contemporary beach house with breathtaking views of Long Island Sound. Conveniently located just 15 mins to Mystic/Stonington; 23 to Foxwoods/Mohegan Sun . Relax on the lower deck and drop a fishing line in the ocean as it greets the seawall at high tide. Or retreat to a private roof deck to enjoy your favorite beverage as you take in the most romantic time of the day, the golden hour featuring beautiful sunsets. Parking for 3-4 cars. We hope you enjoy this escape by the sea!

Top guest favourite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam
4.93 out of 5 average rating, 294 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Guest favourite
A wooden dock stretches over the calm waters, supported by several sturdy posts featuring black caps. The sky above is clear with soft clouds, enhancing the serene coastal atmosphere.
Home in Saybrook Manor
4.93 out of 5 average rating, 100 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

Top guest favourite
A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.
Home in East Lyme
4.97 out of 5 average rating, 209 reviews

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.

Top guest favourite
A cozy cottage exterior is showcased, featuring a gabled roof and wooden siding in earthy tones. A spacious screened porch with rocking chairs invites relaxation, while a nearby shed complements the rustic aesthetic. Surrounding nature highlights seasonal foliage, enhancing the tranquil setting.
Home in Stonington
4.96 out of 5 average rating, 203 reviews

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

Guest favourite
A historic New England home features a classic white exterior with multiple windows. Surrounding greenery includes mature trees and a well-maintained lawn. The side of the house provides a glimpse of a separate structure, enhancing the spacious outdoor area.
Home
4.97 out of 5 average rating, 210 reviews

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.

Guest favourite
A wide view of a sandy beachfront stretches along the coastline, bordered by calm blue waters under a clear sky. Lush greenery can be seen in the distance, suggesting a nearby park or recreation area. Several individuals are spaced along the shore enjoying the beach.
Home in Waterford
4.94 out of 5 average rating, 125 reviews

Salty Breeze - Waterfront Cottage on the Cove

Enjoy your stay in this peaceful waterfront cottage. After the day relax on the 3 season screened- in porch or climate controlled sunroom watching the winter waterfowl on the wintery cove or relax in the backyard next to the fire pit with hot coco. Walking distance to Ocean Beach Park, Waterford Town Beach. Within 30 minutes of Niantic, downtown Mystic, Ferry's to Block, Fisher's and Long Islands, by museums, the Nautilus, Mohegan and Foxwoods Casinos, tons of great restaurants

Top guest favourite
A serene view of the Poquetanuck Bay is captured at dawn, showcasing a calm water surface reflecting pastel hues of pink and purple. Surrounding trees frame the scene, while homes on the opposite shore are silhouetted against the soft morning light.
Home in Preston
4.95 out of 5 average rating, 751 reviews

Entire House Magical Waterfront Getaway

4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!

Popular amenities for house rentals in Old Saybrook

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Quick stats about house rentals in Old Saybrook

  • Total holiday rentals

    Explore 90 holiday rentals in Old Saybrook

  • Nightly prices starting at

    Old Saybrook holiday rentals start at £75 per night before taxes and fees

  • Verified guest reviews

    Over 2,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 of Old Saybrook holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Old Saybrook rentals

  • 4.9 Average rating

    Old Saybrook stays are highly rated by guests – averaging 4.9 out of 5!