Beginning of main content

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Tonight Oct 21 - Oct 22
This weekend Oct 23 - Oct 25
Next weekend Oct 30 - Nov 1

Featured Vacation Homes in Old Saybrook

Get Rates
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.
 
Get Rates
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
Located in Westbrook Center, this vacation home is 0.1 mi (0.2 km) from Westbrook Town Beach and 2.5 mi (4 km) from Tanger Outlets. Adam Stanton House and General Store Museum and Chalker Beach are also within 6 mi (10 km).
 
Get Rates
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.
 
Get Rates
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).
 
Get Rates
Beach is Open for Summer Fun!!! Sweet Summer Beach House in Saybrook Manor

Beach is Open for Summer Fun!!! Sweet Summer Beach House in Saybrook Manor

Old Saybrook, CT
This vacation home includes a garden and barbecue grills.
 
Get Rates
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.
 
Get Rates
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.
 
Get Rates
Seastar Beach House -knollwood Private Beach Association

Seastar Beach House -knollwood Private Beach Association

Old Saybrook, CT
An outdoor tennis court is featured at this vacation home, along with a garden.
 
Get Rates
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.
 
Get Rates
NEW Listing Blue Haven - Fenwood Private Beach Community

NEW Listing Blue Haven - Fenwood Private Beach Community

Old Saybrook, CT
This vacation home includes a garden and barbecue grills.
 
Get Rates
Newly Renovated Near Downtown & Hammonasett Beach

Newly Renovated Near Downtown & Hammonasett Beach

Madison, CT
A garden is available at this vacation home.
 
Get Rates
Capt Nathaniel Clarke Historic Homestead?weddings?reunionsmagnificent Yard?

Capt Nathaniel Clarke Historic Homestead?weddings?reunionsmagnificent Yard?

Old Saybrook, CT
This vacation home features a water park, a garden, and a picnic area. Barbecue grills are provided for your convenience.
 
Map

Old Saybrook Vacation Home Rentals

What kind of vacation do you want in Old Saybrook? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation home is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Old Saybrook that will speak to you.

Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Old Saybrook, including luxury vacation home rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.

Take a look at what we have on offer. You’ll find rental houses close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation homes a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.


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).
 
$239
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 1.5 mi (2.4 km) from General William Hart House and 1.7 mi (2.7 km) from Katharine Hepburn Cultural Arts Center. Harvey's Beach and Chalker Beach are also within 6 mi (10 km).
 
$50
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2.0 out of 5.0 37 Spencer Plain Rd, Old Saybrook, CT
Located in Westbrook Center, this hotel is 1.2 mi (1.9 km) from Chalker Beach and within 3 mi (5 km) of General William Hart House and Katharine Hepburn Cultural Arts Center. Tanger Outlets and Harvey's Beach are also within 3 mi (5 km).
 
*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.