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Vacation rentals in Old Saybrook

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Old Saybrook vacation rentals

Self check-in
Beachfront
Gym
BBQ grill
Laptop-friendly workspace

Old Saybrook beach vacation rentals

Guest favorite
A three-level home is shown, featuring a mix of wood and stone siding. Lush greenery surrounds a stone wall garden, while a spacious balcony extends from the upper level. The inviting entrance displays a garage on the left, with a peaceful driveway leading to the main door.
Vacation home in Westbrook
4.89 out of 5 average rating, 35 reviews

Modern Coastal Home with Pool

Guest favorite
A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.
Home in Branford
4.97 out of 5 average rating, 32 reviews

Adorable Beach House on LI Sound

Guest favorite
A serene outdoor space features four grey Adirondack chairs arranged around a small table, set on a lush green lawn. Surrounding foliage adds a touch of nature, while a clear sky provides a bright backdrop.
Guesthouse in New London
4.97 out of 5 average rating, 109 reviews

Fully Renovated, Ocean Views, Fireplace & Beach

Top guest favorite
A private covered porch is featured, overlooking lush greenery and scenic water views. Two black adirondack chairs are positioned for relaxation, with wooden railings providing safety and support. The horizon showcases a serene marshland, creating a peaceful outdoor setting.
Apartment in Westbrook
5 out of 5 average rating, 7 reviews

Private Guest Suite Water Views

Guest favorite
An aerial view captures the expansive sandy beach stretching along the coastline, adjacent to serene waters reflecting sunlight. Houses line the shore, with some beach chairs positioned near the water's edge, creating a peaceful coastal scene.
Home in Westbrook
4.96 out of 5 average rating, 24 reviews

Barnacle Bay Beach House

Top guest favorite
A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.
Cottage in Guilford
4.94 out of 5 average rating, 268 reviews

The Cottage at Indian Cove

Top guest favorite
A serene view of a quiet street leading to the water, framed by trees. Visible are parked vehicles along the roadside, with the sparkling bay in the background, indicating proximity to the beach. A basketball hoop stands on the right side, contributing to the residential atmosphere.
Home in East Lyme
4.97 out of 5 average rating, 143 reviews

Walk to the beach at Black Point, Niantic, Ct

Top guest favorite
A cozy living area is highlighted by a spacious sofa adorned with a soft throw, accompanied by a wooden coffee table. Natural light streams through large windows, illuminating a rustic fireplace and a decorative sculpture. Bookshelves filled with various books create an inviting atmosphere.
Guesthouse in Mystic
4.98 out of 5 average rating, 285 reviews

True Artist Loft, 5 minutes to downtown Mystic

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Cottage rentals in Old Saybrook

Guest favorite
The living area features large French doors that open to a scenic view of the lake, inviting natural light. A coffee table sits center, adorned with a small vase of flowers. Comfortable seating includes two leather couches facing the lake, with striped area rugs underfoot.
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

Guest favorite
A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.
Cottage in Guilford
4.95 out of 5 average rating, 180 reviews

Luxury cottage by the sea with hot tub and pool

Guest favorite
A comfortable living area features a cozy seating arrangement with a blue sofa and an inviting armchair, set against a rustic stone fireplace. A warm light emanates from above, illuminating the wood-paneled ceiling and vibrant area rug. Large windows allow natural light to fill the space.
Cottage in Hebron
4.88 out of 5 average rating, 140 reviews

Welcome to The Holly at Amston Lake

Top guest favorite
A serene outdoor setting features several Adirondack chairs arranged around a fire pit, surrounded by lush green trees and natural rock formations. The calm river flows gently nearby, with sunlight filtering through the canopy, creating a peaceful retreat atmosphere.
Cottage in Weston
4.96 out of 5 average rating, 137 reviews

The River Loft

Top guest favorite
Cottage in Guilford
4.99 out of 5 average rating, 102 reviews

Waterfront Joshua Cove Cottage with private beach.

Guest favorite
A backyard patio area is shown, featuring a seating arrangement of several chairs and a table. A fire pit is positioned on a stone surface, surrounded by grass and landscaping. The view overlooks the lake, with boats visible in the background and lush trees framing the scene.
Cottage in Moodus
4.9 out of 5 average rating, 131 reviews

Direct Waterfront Cottage on Moodus Reservoir.

Guest favorite
A spacious living area is featured, with large windows offering unobstructed views of the lake. Comfortable seating includes a sectional sofa and accent chairs, complemented by warm wood tones. The kitchen area is visible, showcasing a large island and wooden cabinetry.
Cottage in Montville
4.95 out of 5 average rating, 106 reviews

Beautiful lakefront retreat just 15 mins to casino

Guest favorite
An outdoor space is presented featuring a gravel area surrounded by comfortable blue Adirondack chairs. A fire pit is centrally located, and a wooden deck can be seen in the background, furnished with a dining set and shaded by a bright yellow umbrella.
Cottage in Chester
4.97 out of 5 average rating, 272 reviews

Updated cottage "Beriozka" on Cedar Lake

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House rentals in Old Saybrook

Guest favorite
A serene garden space features lush green foliage and vibrant pink flowers, with a rustic wooden chair positioned to overlook a gentle waterfall. The surrounding trees provide a natural canopy, creating a peaceful atmosphere for relaxation.
Home in Chester
4.98 out of 5 average rating, 210 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Guest favorite
A charming stone exterior is visible, featuring a private entrance with a sliding glass door. The path is made of stone, surrounded by a well-maintained lawn. In the background, sitting areas and greenery are discernible, enhancing a serene outdoor experience.
Home in Clinton
4.94 out of 5 average rating, 141 reviews

Amazing 2BR Riverfront Gem

Guest favorite
The living area features a large sectional sofa with a throw pillow, a dark coffee table, and a dining area with a wood table. Sliding glass doors open to a scenic view of the Thames River and the outdoor deck.
Home in Uncasville
4.91 out of 5 average rating, 127 reviews

Thames River Cottage · Near Casinos + USCGA

Guest favorite
A spacious outdoor deck is offered, featuring comfortable seating arranged beneath a bright red umbrella. Potted plants add color, while string lights provide soft illumination. An expansive water view is visible, framed by lush greenery and a serene sky.
Home in East Lyme
4.93 out of 5 average rating, 29 reviews

Stylish Retreat Waterviews

Superhost
A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.
Home in Westbrook
4.79 out of 5 average rating, 125 reviews

The Dragon Fly Garden

Superhost
Home in Essex
5 out of 5 average rating, 4 reviews

Mid-Century 4 bedrooms with Water View & Access

Guest favorite
A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.
Home in Southington
4.95 out of 5 average rating, 116 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

Top guest favorite
The exterior of the Secret Stone Cottage is presented, featuring a charming stone facade and a multi-pitched roof. Lush greenery surrounds the property, complemented by a well-maintained lawn and a paved driveway leading to an adjacent garage.
Home in Westbrook
5 out of 5 average rating, 25 reviews

Secret Seaside Stone Cottage

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Quick stats about vacation rentals in Old Saybrook

  • Total rentals

    120 properties

  • Nightly prices starting at

    G$10,491 GYD before taxes and fees

  • Total number of reviews

    3.4K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Frequently Asked Questions

  • What types of vacation rentals are available in Old Saybrook?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Old Saybrook. From over 20 cottage rentals to over 90 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Old Saybrook?

    Yes! Work meets play with ease at over 60 vacation rentals in Old Saybrook featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Old Saybrook?

    Four-legged friends are welcome in Old Saybrook. Choose from more than 40 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Old Saybrook?

    Experience the best of Old Saybrook with our cottage rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Old Saybrook have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Saybrook have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Saybrook have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Old Saybrook?

    Old Saybrook has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore