Book Holiday Homes in Old Saybrook

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Featured Holiday Homes in Old Saybrook

Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic

Mystic CT
The price is AU$521 per night from 24 Mar to 25 Mar
AU$521
24 Mar - 25 Mar
includes taxes & fees
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 ...
Opens in a new windowCharming Historic House in Downtown Mystic
Cape Cod home in great location! Walk to downtown

Cape Cod home in great location! Walk to downtown

Stonington CT
With a stay at this vacation home in Pawcatuck, you'll be within a 15-minute drive of Mystic Aquarium and Institute for Exploration and Mystic Seaport.
Opens in a new windowCape Cod home in great location! Walk to downtown
Oceanfront Getaway -  Quiet, Firepit + Pvt Beach

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

East Haven CT
The price is AU$940 per night from 31 Mar to 1 Apr
AU$940
31 Mar - 1 Apr
includes taxes & fees
With a stay at this vacation home in East Haven (Morgan Point), you'll be within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowOceanfront Getaway - Quiet, Firepit + Pvt Beach
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The SandPiper

The SandPiper

Greenport, NY
With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from East End Seaport ...
Opens in a new windowThe SandPiper
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton CT
With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes ...
Opens in a new windowLarge Charming Historic House close to Beaches
New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

Westerly RI
The price is AU$1,285 per night from 3 Apr to 4 Apr
AU$1,285
3 Apr - 4 Apr
includes taxes & fees
With a stay at this vacation home in Westerly, you'll be within a 5-minute drive of East Beach and Misquamicut State Beach.
Opens in a new windowNew for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
Downtown Mystic Home  Private Driveway Fenced in Yard Discounted longer stays

Downtown Mystic Home Private Driveway Fenced in Yard Discounted longer stays

Mystic CT
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 ...
Opens in a new windowDowntown Mystic Home Private Driveway Fenced in Yard Discounted longer stays
Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access

Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access

East Hampton NY
With a stay at this vacation home in East Hampton (Clearwater Beach), you'll be within a 5-minute drive of The Hamptons Beaches and Three Mile Harbor.
Opens in a new windowSerene Hamptons Retreat with Pool, Bocce Court & Private Beach Access
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Mystic CT
The price is AU$386 per night from 22 Mar to 23 Mar
AU$386
22 Mar - 23 Mar
includes taxes & fees
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.
Opens in a new windowCharming 1845 Home in the Heart of Mystic – Walk to Everything!
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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
985 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$1,285
Popular accommodation
Charming Historic House in Downtown Mystic, Cape Cod home in great location! Walk to downtown , Oceanfront Getaway - Quiet, Firepit + Pvt Beach, The SandPiper , Large Charming Historic House close to Beaches, New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!, Downtown Mystic Home Private Driveway Fenced in Yard Discounted longer stays, Serene Hamptons Retreat with Pool, Bocce Court & Private Beach Access, Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Top trending hotels in Old Saybrook

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$525 per night from 23 Mar to 24 Mar
AU$525
23 Mar - 24 Mar
includes taxes & fees
With a stay at Saybrook Point Resort & Marina in Old Saybrook (Old Saybrook Center), you'll be steps from Fort Saybrook Monument Park and a 2-minute drive from ...
Opens in a new windowSaybrook Point Resort & Marina
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Crystal Lake Town Park.
Opens in a new windowPier Blue Inn Old Saybrook - Essex
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$152 per night from 29 Mar to 30 Mar
AU$152
29 Mar - 30 Mar
includes taxes & fees
A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, within a 10-minute drive of Essex Steam Train and Essex Library.
Opens in a new windowQuality Inn Old Saybrook - Westbrook
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New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 30 Mar to 31 Mar
AU$178
30 Mar - 31 Mar
includes taxes & fees
New Haven Hotel is centrally located in New Haven, a 4-minute walk from Shubert Theater and 5 minutes by foot from New Haven Green.
Opens in a new windowNew Haven Hotel
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.