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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

Stay near Old Saybrook's top sights

Florence Griswold Museum65 locals recommend
The Katharine Hepburn Cultural Arts Center52 locals recommend
The Griswold Inn49 locals recommend
Westbrook Outlets44 locals recommend
Connecticut River Museum38 locals recommend
Big Y World Class Market34 locals recommend

Old Saybrook beach vacation rentals

Guest favorite
A sunlit view of a sandy beach stretches towards the horizon, with gentle waves lapping at the shore. Colorful umbrellas dot the sandy area, and a wooden walkway runs parallel to the beachfront. In the distance, sailboats can be seen on the calm water.
Home in New London
4.93 out of 5 average rating, 351 reviews

Amazing Beach House

Guest favorite
Outdoor seating is arranged on a wooden deck, featuring sleek loungers. Surrounding planters add greenery, while the view stretches to the calm water and distant horizon. Sunlight brightens the area, enhancing the serene ambiance of the beachfront setting.
Cottage in North Fork
4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Superhost
A wide-angle view captures the beach and waterfront community, showcasing houses lined along the shore. A sandy beach meets calm waters, with a jetty extending into the sea. Fluffy clouds float in a clear blue sky above the scenic landscape.
Guesthouse in Milford
4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Guest favorite
The exterior of the vacation home features a welcoming front deck with a table and chairs, shaded by a patio umbrella. A gravel pathway leads to the entrance, complemented by a white panel facade and multiple windows that allow natural light to enter.
Home in Westbrook
4.82 out of 5 average rating, 11 reviews

Beachside @ 455 Seaside

Superhost
A panoramic view showcases a tranquil beach scene under a double rainbow arching over the sea. Gentle waves lap at the shore, while a sandy beach space with sparse grass is visible. A blue umbrella and chairs provide a welcoming spot for relaxation.
Cottage in Milford
4.78 out of 5 average rating, 32 reviews

Cheerful 2 bedroom cottage on beach

Guest favorite
A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.
Home in West Haven
4.95 out of 5 average rating, 19 reviews

Beach House steps from sand & Amazing Views

Guest favorite
The image captures a serene view of the ocean from a wooden porch, showcasing calm waters and a sandy beach. A neatly maintained lawn extends to the shoreline, with a few small boats visible in the distance under a clear blue sky.
Home in East Lyme
4.96 out of 5 average rating, 186 reviews

Beachfront Paradise

Guest favorite
A shaded porch featuring a gray wooden floor extends towards the water, with hanging planters displaying vibrant flowers. Ocean views are visible in the distance, and a small blue boat is anchored along the shoreline. Soft light creates gentle shadows across the space.
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

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Cottage rentals in Old Saybrook

Guest favorite
A red chair is positioned on a wooden deck overlooking a calm lake. The surface of the water reflects surrounding green trees and a sky filled with fluffy clouds, creating a serene atmosphere.
Cottage in Ledyard
4.89 out of 5 average rating, 195 reviews

Waterfront cottage overhanging the water!

Top guest favorite
A cozy cottage is presented with a wooden deck and a sloped roof. The deck features a dining table surrounded by chairs. Lush greenery and neatly trimmed bushes surround the pathway leading to the cottage, with a serene lake visible in the background.
Cottage in Hopkinton
4.98 out of 5 average rating, 138 reviews

Lakeside Cottage in Hope Valley, RI

Guest favorite
A telescope is positioned on a tripod near a row of three windows, offering views of the serene waters of Long Island Sound. Light streams in, highlighting a wooden table and a striped armchair in the cozy seating area.
Cottage in Woodmont
4.88 out of 5 average rating, 147 reviews

Waterfront Beach Cottage

Top guest favorite
Cottage in Guilford
4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

Top guest favorite
A patio area features dark wicker seating arranged around a low table, with a wood dining set positioned nearby. A large umbrella provides shade, while lush greenery surrounds the space, creating a serene outdoor environment for relaxation.
Cottage in Redding
5 out of 5 average rating, 103 reviews

Star Cottage

Guest favorite
A charming street scene captures vintage-style buildings, adorned with holiday wreaths and white lights. Soft snowfall creates a serene atmosphere, while a clock tower is visible in the background, contributing to the quaint character of the area.
Cottage in Goshen
4.94 out of 5 average rating, 123 reviews

Country Cottage in Goshen

Guest favorite
The exterior of the modern cottage is presented, featuring a sleek, dark facade accentuated by landscaped stone pathways. A spacious porch offers a welcoming entry, complemented by large windows that provide natural light. Surrounding hills are visible in the background.
Cottage in Cornwall
4.93 out of 5 average rating, 147 reviews

Newly Built Cottage in Housatonic Valley

Guest favorite
The cozy bedroom features a sloped wooden ceiling and warm, natural light filtering through a window. A bed with a checkered duvet is flanked by two bedside lamps, while a woven basket sits at the foot, adding a touch of rustic charm.
Cottage in Goshen
4.95 out of 5 average rating, 150 reviews

Stuart Cottage/Minutes to Mohawk Ski Area

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House rentals in Old Saybrook

Guest favorite
A charming Cape Cod cottage is showcased, featuring a light gray shingled exterior and blue door. The front yard is adorned with green grass and small shrubs, while steps lead to the entrance. Tall trees frame the property, providing a sense of privacy.
Home in Sag Harbor
4.85 out of 5 average rating, 160 reviews

Sag Harbor House for rent.

Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

Top guest favorite
A single-story home is situated on a well-kept lawn with lush greenery and small bushes lining the front. The exterior features light-colored siding and a dark roof, complemented by multiple large windows that enhance natural light.
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

Top guest favorite
A traditional two-story house is framed by well-maintained greenery and shrubs. A paved driveway leads to the entrance, while a detached garage is visible to the side. The exterior features white siding with red trim and multiple windows, creating a welcoming appearance.
Home in Southampton
4.96 out of 5 average rating, 119 reviews

4 Bed, 2 Bath, Southampton, L.I.

Top guest favorite
A charming single-story house features a classic shingle exterior with a brick chimney. A spacious front deck is bordered by white railings and overlooks a manicured lawn surrounded by trees. Soft sunlight filters through the leaves, enhancing the serene setting.
Home in East Hampton
4.95 out of 5 average rating, 230 reviews

Private beach, fully updated cottage, on 2 acres.

Guest favorite
A dining room table with eight chairs is set beneath ambient lighting. The room opens to a cozy living area featuring a comfortable sofa and blue curtains. A doorway leads to a well-lit kitchen, enhancing the home's spacious layout.
Home in New London
4.95 out of 5 average rating, 133 reviews

House in NL near CGA, Sub Base, Mohegan Casino

Top guest favorite
The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.
Home in Old Saybrook
4.97 out of 5 average rating, 121 reviews

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

Top guest favorite
A two-story home features a grey exterior with white trim and a bright blue front door. Sturdy stone steps lead up to the entrance, flanked by well-maintained landscaping that includes green plants. The property is bordered by a wooden fence, offering privacy.
Home in Westerly
4.98 out of 5 average rating, 132 reviews

Cute and Close to Beaches and Town

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Quick stats about vacation rentals in Old Saybrook

  • Total rentals

    120 properties

  • Nightly prices starting at

    G$10,460 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 90 house rentals to over 20 cottage 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 30 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.

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