Book Holiday Homes in Old Saybrook

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Featured Holiday Homes in Old Saybrook

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

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

Stonington
The price is AU$904 per night from 4 Dec to 5 Dec
AU$904
includes taxes & fees
4 Dec - 5 Dec
With a stay at this vacation home, you'll be centrally located in Mystic, within a 5-minute drive of Mystic Seaport and Mystic Aquarium and Institute for ...
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic.
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Stonington
The price is AU$341 per night from 9 Dec to 10 Dec
AU$341
includes taxes & fees
9 Dec - 10 Dec
When you stay at this vacation home in Stonington, you'll be near the beach, within a 10-minute drive of Mystic Aquarium and Institute for Exploration and Mystic ...
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Coates Suite · Cheerful Historic 3 BR Townhouse - Downtown Mystic

Coates Suite · Cheerful Historic 3 BR Townhouse - Downtown Mystic

Stonington
With a stay at this vacation home in Mystic, you'll be within a 5-minute drive of Mystic Seaport and Mystic Aquarium and Institute for Exploration.
Coates Suite · Cheerful Historic 3 BR Townhouse - Downtown Mystic
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Waterfront Beach House

Waterfront Beach House

Clinton
Located in Clinton, this vacation home is by the ocean, within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store ...
Waterfront Beach House
Perfect 3-bedroom family house in beautiful Westerly, Rhode Island!

Perfect 3-bedroom family house in beautiful Westerly, Rhode Island!

2 out of 5
Westerly
Located in Westerly, this vacation home is by the sea, within a 5-minute drive of Misquamicut State Beach and East Beach.
Perfect 3-bedroom family house in beautiful Westerly, Rhode Island!
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Branford
Located in Branford, this vacation home is by the ocean, within a 10-minute drive of Polished and Stony Creek Brewery.
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Unbeatable Downtown Mystic Location

Unbeatable Downtown Mystic Location

Mystic
With a stay at this vacation home in Mystic, you'll be within a 5-minute drive of Mystic Seaport and Mystic Aquarium and Institute for Exploration.
Unbeatable Downtown Mystic Location
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

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

Clinton
When you stay at this vacation home in Clinton, you'll be near the beach and 11 minutes by foot from Clinton Town Beach.
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Historic Three Bedroom Townhouse -- Downtown Mystic

Historic Three Bedroom Townhouse -- Downtown Mystic

Mystic
When you stay at this vacation home in Mystic, you'll be near the beach, within a 5-minute drive of Mystic Seaport and Mystic Aquarium and Institute for ...
Historic Three Bedroom Townhouse -- Downtown Mystic
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
845 Holiday Homes
Lowest Price
AU$122
Highest Price
AU$904
Popular accommodation
Beautifully Restored 1890’s House in beautiful & picturesque downtown Mystic. , Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village, Coates Suite · Cheerful Historic 3 BR Townhouse - Downtown Mystic, Waterfront Beach House, Perfect 3-bedroom family house in beautiful Westerly, Rhode Island!, Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub , Unbeatable Downtown Mystic Location, Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Historic Three Bedroom Townhouse -- Downtown Mystic

Top trending hotels in Old Saybrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 8 Dec to 9 Dec
AU$134
includes taxes & fees
8 Dec - 9 Dec
A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, a 5-minute drive from Essex Steam Train and 5 minutes from Essex ...
Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 26 Nov to 27 Nov
AU$122
includes taxes & fees
26 Nov - 27 Nov
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Saybrook Country Barn.
Pier Blue Inn Old Saybrook - Essex
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$507 per night from 2 Dec to 3 Dec
AU$507
includes taxes & fees
2 Dec - 3 Dec
With a stay at Saybrook Point Resort & Marina in Old Saybrook (Old Saybrook Center), you'll be a 4-minute walk from Connecticut River and within a 5-minute drive ...
Saybrook Point Resort & Marina
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Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino

3.5 out of 5
411A & 411B Norwich Westerly Road, North Stonington, CT
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 15 Dec to 16 Dec
AU$180
includes taxes & fees
15 Dec - 16 Dec
Located in North Stonington, Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino is within a 10-minute drive of Lake of Isles and Jonathan Edwards ...
Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino
Don't see what you're looking for?
See all available properties in Old Saybrook
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.