Book Holiday Homes in Old Saybrook

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Featured Holiday Homes in Old Saybrook

The Secret Mermaid in downtown Mystic! Beautiful & just remodeled!

The Secret Mermaid in downtown Mystic! Beautiful & just remodeled!

Groton
Book a stay at this family-friendly vacation home in Mystic. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Mystic Seaport and Mystic ...
The Secret Mermaid in downtown Mystic! Beautiful & just remodeled!
Brand new home minutes to casino

Brand new home minutes to casino

Ledyard
The price is NZ$656 per night from 30 Dec to 31 Dec
NZ$656
includes taxes & fees
30 Dec - 31 Dec
Stay at this vacation home in Ledyard. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Mohegan Sun Casino and Foxwoods Resort Casino ...
Brand new home minutes to casino
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
Book a stay at this family-friendly vacation home in East Lyme. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the helpful staff ...
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
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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

Pawcutuck
Book a stay at this family-friendly vacation home in Stonington. Enjoy free WiFi, a garden, and patios. Popular attractions Mystic Aquarium and Institute for ...
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River

Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River

East Haddam
Book a stay at this family-friendly vacation home in East Haddam. Enjoy free WiFi, private pools, and a water park. Popular attractions St. Stephen's Church ...
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River
Historic Three Bedroom Townhouse -- Downtown Mystic

Historic Three Bedroom Townhouse -- Downtown Mystic

Mystic
The price is NZ$947 per night from 4 Jan to 5 Jan
NZ$947
includes taxes & fees
4 Jan - 5 Jan 2025
Stay at this vacation home in Mystic. Enjoy free WiFi and air conditioning. Popular attractions Mystic Seaport and Mystic Aquarium and Institute for Exploration ...
Historic Three Bedroom Townhouse -- Downtown Mystic
Spectacular home with an amazing river view

Spectacular home with an amazing river view

Groton
Book a stay at this family-friendly vacation home in Groton. Enjoy free WiFi, a garden, and a pool table. Popular attractions The Submarine Force Library and ...
Spectacular home with an amazing river view
Charming beach home, complete with pool & cozy guest house!

Charming beach home, complete with pool & cozy guest house!

Clinton
Book a stay at this family-friendly vacation home in Clinton. Enjoy free WiFi, private pools, and a garden. Popular attractions Indian River Marina and Adam ...
Charming beach home, complete with pool & cozy guest house!
Elegant Norwich House w/ Billiards Room & Ballroom

Elegant Norwich House w/ Billiards Room & Ballroom

Norwich
Stay at this vacation home in Norwich. Enjoy a garden, a pool table, and patios. Popular attractions Mohegan Sun Casino and Mohegan Sun Arena are located ...
Elegant Norwich House w/ Billiards Room & Ballroom
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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
838 Holiday Homes
Lowest Price
NZ$140
Highest Price
NZ$947
Popular accommodation
The Secret Mermaid in downtown Mystic! Beautiful & just remodeled!, Brand new home minutes to casino, Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages, Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River, Historic Three Bedroom Townhouse -- Downtown Mystic, Spectacular home with an amazing river view, Charming beach home, complete with pool & cozy guest house!, Elegant Norwich House w/ Billiards Room & Ballroom

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 NZ$620 per night from 5 Jan to 6 Jan
NZ$620
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
Saybrook Point Resort & Marina
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 NZ$173 per night from 29 Dec to 30 Dec
NZ$173
includes taxes & fees
29 Dec - 30 Dec
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 NZ$140 per night from 23 Dec to 24 Dec
NZ$140
includes taxes & fees
23 Dec - 24 Dec
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Pier Blue Inn Old Saybrook - Essex
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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$223 per night from 29 Dec to 30 Dec
NZ$223
includes taxes & fees
29 Dec - 30 Dec
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
New Haven Hotel
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.

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