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
Stay at this holiday home in Pawcatuck. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mystic Aquarium and Institute for Exploration ...
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
Stay at this holiday home in Stonington. Enjoy laundry facilities and air conditioning. Popular attractions Mystic Aquarium and Institute for Exploration and ...
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
Stay at this holiday home in Clinton. Enjoy a garden, laundry facilities and patios. Popular attractions Adam Stanton House and General Store Museum and Indian ...
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
Stay at this family-friendly holiday home in Niantic. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions Attawan Beach and Giants Neck ...
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
Stay at this family-friendly holiday home in Preston. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Foxwoods Resort Casino and Mohegan Sun ...
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 NZ$577 per night from 17 Dec to 18 Dec
NZ$577
17 Dec - 18 Dec
includes taxes & fees
Stay at this holiday home in Groton. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Mystic Seaport and Mystic Aquarium and ...
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
Stay at this beach holiday home in Westerly. Enjoy free Wi-Fi, a beach locale and a water park. Popular attractions Misquamicut State Beach and Water Wizz of ...
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
Stay at this family-friendly holiday home in East Lyme. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the helpful staff in their ...
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Aqua Vista

Aqua Vista

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Railroad Museum of Long Island and 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
NZ$226
Highest Price
NZ$655
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
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
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 NZ$655 per night from 21 Dec to 22 Dec
NZ$655
21 Dec - 22 Dec
includes taxes & fees
Stay at this spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in their reviews. ...
Opens in a new windowSaybrook Point Resort & Marina
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
Fully refundableReserve now, pay when you stay
The price is NZ$392 per night from 4 Jan to 5 Jan
NZ$392
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this luxury resort in Montville. Enjoy free Wi-Fi, free parking and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in their ...
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 NZ$226 per night from 25 Dec to 26 Dec
NZ$226
25 Dec - 26 Dec
includes taxes & fees
Stay at this business-friendly hotel in New Haven. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff and the ...
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.