Book Holiday Homes in Old Saybrook

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Featured Holiday Homes in Old Saybrook

Secluded Waterfront Location With Dock

Secluded Waterfront Location With Dock

Stonington CT
Located in Pawcatuck, this vacation home is by the sea, within a 10-minute drive of Atlantic Beach Park and Wilcox Park.
Opens in a new windowSecluded Waterfront Location With Dock
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Stonington CT
Located in Stonington (Wequetequock), this vacation home is within a 10-minute drive of Mystic Aquarium and Institute for Exploration and Mystic Seaport.
Opens in a new windowAmazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
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
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Walk to the  beach at Black Point, Niantic, Ct.

Walk to the beach at Black Point, Niantic, Ct.

Niantic CT
The price is AU$492 per night from 29 Dec to 30 Dec
AU$492
29 Dec - 30 Dec
includes taxes & fees
When you stay at this vacation home in Niantic, you'll be near the beach and within a 5-minute drive of Attawan Beach.
Opens in a new windowWalk to the beach at Black Point, Niantic, Ct.
Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge

Preston CT
When you stay at this vacation home in Preston, you'll be on the waterfront, within a 5-minute drive of Foxwoods Resort Casino and Grand Theater at Foxwoods ...
Opens in a new windowWaterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge
Oak Grove Cottage - in the foothills of Mystic

Oak Grove Cottage - in the foothills of Mystic

Groton CT
The price is AU$506 per night from 16 Dec to 17 Dec
AU$506
16 Dec - 17 Dec
includes taxes & fees
With a stay at this vacation home in Groton, you'll be within a 10-minute drive of Mystic Aquarium and Institute for Exploration and Mystic Seaport.
Opens in a new windowOak Grove Cottage - in the foothills of Mystic
Amazing Ocean Front 2 Story Home, Steps Away From The Water

Amazing Ocean Front 2 Story Home, Steps Away From The Water

Westerly RI
With a stay at this vacation home in Westerly, you'll be on the beach, just a 4-minute walk from East Beach and 13 minutes by foot from Misquamicut State ...
Opens in a new windowAmazing Ocean Front 2 Story Home, Steps Away From The Water
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

East Lyme CT
When you a stay at this vacation home in East Lyme, you'll be by the sea, just steps from Cedar Ridge Golf Course and White Gate Farm.
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Aqua Vista

Aqua Vista

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 windowAqua Vista
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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$197
Highest Price
AU$572
Popular accommodation
Secluded Waterfront Location With Dock, Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages, Large Charming Historic House close to Beaches, Walk to the beach at Black Point, Niantic, Ct., Waterfront 3-bedroom house less an 1 mile to Foxwoods and Great Wolf Lodge, Oak Grove Cottage - in the foothills of Mystic, Amazing Ocean Front 2 Story Home, Steps Away From The Water, Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Aqua Vista

Top trending hotels in Old Saybrook

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
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.
Opens in a new windowPier 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$572 per night from 21 Dec to 22 Dec
AU$572
21 Dec - 22 Dec
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 4 minutes by foot from ...
Opens in a new windowSaybrook Point Resort & Marina
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
The price is AU$315 per night from 7 Jan to 8 Jan
AU$315
7 Jan - 8 Jan 2026
includes taxes & fees
Located in Montville, Mohegan Sun is connected to the convention center, within a 15-minute walk of Mohegan Sun Arena and Mohegan Sun Casino.
Opens in a new windowMohegan Sun
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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$197 per night from 25 Dec to 26 Dec
AU$197
25 Dec - 26 Dec
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.

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^Subject to availability and chosen travel dates.