Book Holiday Homes in Old Saybrook

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Featured Holiday Homes in Old Saybrook

Cozy 2 bedroom home located minutes from downtown

Cozy 2 bedroom home located minutes from downtown

New Haven
Stay at this vacation home in New Haven. Enjoy free WiFi, laundry facilities, and cable/satellite TV service. Popular attractions Yale Bowl and Cullman-Heyman ...
Opens in a new windowCozy 2 bedroom home located minutes from downtown
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 vacation 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
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 ...
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
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Modern Cape Downtown Mystic

Modern Cape Downtown Mystic

Mystic
Stay at this vacation home in Mystic. Enjoy a garden, laundry facilities, and patios. Popular attractions Mystic Seaport and Mystic Aquarium and Institute for ...
Opens in a new windowModern Cape Downtown Mystic
McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale

West Haven
The price is NZ$906 per night from 7 Oct to 8 Oct
NZ$906
7 Oct - 8 Oct
includes taxes & fees
Book a stay at this family-friendly vacation home in West Haven. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Cullman-Heyman ...
Opens in a new windowMcAngel Haven: 5 mins from Yale
Sweet Mystic Retreat

Sweet Mystic Retreat

Stonington
Stay at this vacation home in Mystic. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mystic Seaport and Mystic Aquarium and Institute ...
Opens in a new windowSweet Mystic Retreat
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Branford
Stay at this vacation home in Branford. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Double Beach and Stony Creek Brewery ...
Opens in a new windowBEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
5 Minute Walk to Downtown Mystic

5 Minute Walk to Downtown Mystic

Mystic
Stay at this vacation home in Mystic. Enjoy a garden, laundry facilities, and patios. Popular attractions Mystic Seaport and Mystic Aquarium and Institute for ...
Opens in a new window5 Minute Walk to Downtown Mystic
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
The price is NZ$1,177 per night from 23 Oct to 24 Oct
NZ$1,177
23 Oct - 24 Oct
includes taxes & fees
Stay at this vacation home in Westerly. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Misquamicut State Beach and Water Wizz of Westerly ...
Opens in a new windowNew for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!
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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
1126 Holiday Homes
Lowest Price
NZ$160
Highest Price
NZ$1,177
Popular accommodation
Cozy 2 bedroom home located minutes from downtown, Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages, Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Modern Cape Downtown Mystic , McAngel Haven: 5 mins from Yale, Sweet Mystic Retreat , BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!, 5 Minute Walk to Downtown Mystic, New for 2025 3 Bedroom Retreat 1 Mile from Westerly’s Beautiful Beaches!

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
The price is NZ$160 per night from 29 Sept to 30 Sept
NZ$160
29 Sept - 30 Sept
includes taxes & fees
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. ...
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$742 per night from 14 Oct to 15 Oct
NZ$742
14 Oct - 15 Oct
includes taxes & fees
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 ...
Opens in a new windowSaybrook 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$195 per night from 13 Oct to 14 Oct
NZ$195
13 Oct - 14 Oct
includes taxes & fees
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 ...
Opens in a new windowQuality Inn Old Saybrook - Westbrook
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Hilltop Inn and Suites, near Foxwoods Casino

Hilltop Inn and Suites, near Foxwoods Casino

2.5 out of 5
373 Norwich Westerly Rd, North Stonington, CT
Fully refundableReserve now, pay when you stay
Stay at this hotel in North Stonington. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient ...
Opens in a new windowHilltop Inn and Suites, 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.