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Featured Vacation Homes in Old Saybrook

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The Beach House at Waters Edge Resort & Spa

The Beach House at Waters Edge Resort & Spa

Westbrook, CT
This vacation home features an indoor pool and an outdoor tennis court. Enjoy the fitness center and conveniences like a garden and barbecue grills.
 
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Relaxing Summer Rental, Walking Distance to the Beach, Short Ride to the Outlets

Relaxing Summer Rental, Walking Distance to the Beach, Short Ride to the Outlets

Westbrook, CT
This vacation home features barbecue grills.
 
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Convenience and Privacy in Exclusive North Cove! Close to Beaches and Downtown!

Convenience and Privacy in Exclusive North Cove! Close to Beaches and Downtown!

Old Saybrook, CT
A fitness center is featured at this vacation home, along with a garden.
 
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Peace Barn in the Heart of the CT River Valley

Peace Barn in the Heart of the CT River Valley

Deep River, CT
Located in Deep River Center, this vacation home is 0.6 mi (1 km) from Plattwood Park and within 3 mi (5 km) of Museum of Fife and Drum and Connecticut Valley Railroad State Park Trail. Ivoryton Playhouse and Selden Neck State Park are also within 3 mi (5 km).
 
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The Showell Manor at Waters Edge Resort & Spa

The Showell Manor at Waters Edge Resort & Spa

Westbrook, CT
This resort features an indoor pool and an outdoor tennis court. A spa tub is also provided.
 
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New! Quiet Clinton House Steps to Private Beaches!

New! Quiet Clinton House Steps to Private Beaches!

Clinton, Connecticut
Situated on the waterfront, this vacation home is 0.3 mi (0.4 km) from Clinton Town Beach and within 3 mi (5 km) of Adam Stanton House and General Store Museum and Indian River Marina. Clinton Crossing Premium Outlets is 3.1 mi (5 km) away.
 
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Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd

Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd

Madison, CT
This vacation home features barbecue grills.
 
$425
Newly Renovated Near Downtown & Hammonasett Beach

Newly Renovated Near Downtown & Hammonasett Beach

Madison, CT
A garden is available at this vacation home.
 
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Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd

Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd

Madison, CT
This vacation home includes a garden and barbecue grills.
 
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Beach Front Property Steps From Long Island Sound!

Beach Front Property Steps From Long Island Sound!

Westbrook, CT
Located in Westbrook Center, this vacation home is 1.3 mi (2.2 km) from Westbrook Town Beach and 1.7 mi (2.7 km) from Tanger Outlets. Essex Steam Train and Chalker Beach are also within 6 mi (10 km).
 
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Large 3 BR Home w/ Private Beach Access

Large 3 BR Home w/ Private Beach Access

Clinton, CT
This vacation home includes a garden and barbecue grills.
 
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Find the Best Vacation Homes in Old Saybrook

Why book a vacation home in Old Saybrook?

Vacation homes in Old Saybrook make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in Old Saybrook?

Private Old Saybrook rental homes range between $53 - $425 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in Old Saybrook vacation home rentals. You might look for Old Saybrook rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Old Saybrook offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in Old Saybrook?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Old Saybrook. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Old Saybrook hotels and vacation homes that best suit your stay. We also have deals for flights, and Old Saybrook car rentals. You’ll save even more when you bundle your items into a Old Saybrook vacation package!

How many vacation homes are available to book in Old Saybrook?

There are 38 rental homes in Old Saybrook. Enter your travel dates to check availability.

How do I find the best price for a vacation home in Old Saybrook?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.


Top trending hotels in Old Saybrook

See all 176 Properties in Old Saybrook
$160
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5.0 1525 Boston Post Road, Westbrook, CT
This Westbrook Center resort is on the beach, 1.7 mi (2.8 km) from Tanger Outlets, and within 6 mi (10 km) of Harvey's Beach and Essex Steam Train. Clinton Crossing Premium Outlets and Ivoryton Playhouse are also within 9 mi (15 km).
 
$267
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5.0 2 Bridge St, Old Saybrook, CT
Located in Old Saybrook Center, this spa hotel is within 3 mi (5 km) of General William Hart House, Katharine Hepburn Cultural Arts Center, and Connecticut Valley Railroad State Park Trail. Harvey's Beach and Chalker Beach are also within 6 mi (10 km).
 
$53
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 out of 5.0 1430 Boston Post Rd, Old Saybrook, CT
Located in Saybrook Manor, this hotel is 0.9 mi (1.4 km) from Chalker Beach and within 3 mi (5 km) of General William Hart House and Katharine Hepburn Cultural Arts Center. Harvey's Beach is 2 mi (3.3 km) away.
 
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.