Book Holiday Homes in Old Saybrook
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Featured Holiday Homes in Old Saybrook

Charming Historic House in Downtown Mystic

Waterfront House with picture-perfect views from all 3 levels.

Romantic Guesthouse in Historic Downtown Waterfront District!

Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.

Luxe Lake House in Connecticut

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Magical Getaway · Historic, Seaside Mystic Getaway, Walk To Seaport

3-bedroom vacation home just a 5-min walk to Main Street, Mystic

A Family Heirloom - Historic 1839 Downtown Mystic Home
Old Saybrook Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Old Saybrook vacation homes are the perfect way for you to wing it.
Holiday houses in Old Saybrook let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Old Saybrook in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Old Saybrook adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Old Saybrook with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Old Saybrook vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Old Saybrook Holiday Homes essential information
Accommodation | 857 Holiday Homes |
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Lowest Price | AU$126 |
Highest Price | AU$1,419 |
Popular accommodation | Charming Historic House in Downtown Mystic, Waterfront House with picture-perfect views from all 3 levels., Romantic Guesthouse in Historic Downtown Waterfront District!, Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic. , Luxe Lake House in Connecticut, Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Magical Getaway · Historic, Seaside Mystic Getaway, Walk To Seaport, 3-bedroom vacation home just a 5-min walk to Main Street, Mystic , A Family Heirloom - Historic 1839 Downtown Mystic Home |
More accommodations in Old Saybrook
Top trending hotels in Old Saybrook

Saybrook Point Resort & Marina

Pier Blue Inn Old Saybrook - Essex

Quality Inn Old Saybrook - Westbrook

Spark by Hilton Mystic Groton
More ways to explore Old Saybrook
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^Subject to availability and chosen travel dates.