Old Saybrook Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Old Saybrook vacation rentals

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is CA $130
CA $298 total
includes taxes & fees
Feb 24 - Feb 25
Lakefront Boho Tiny House

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is CA $137
CA $307 total
includes taxes & fees
Feb 24 - Feb 25
Cozy Lakefront Tiny House

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $274
CA $484 total
includes taxes & fees
Mar 1 - Mar 2
The gardners Cottage 1 mile from long Island Sound - pet friendly

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is CA $205
CA $503 total
includes taxes & fees
Feb 10 - Feb 11
Charming 2-bedroom house with WiFi, AC in lovely Waterford

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (35 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is CA $110
CA $246 total
includes taxes & fees
Feb 10 - Feb 11
1-bedroom cottage with Grove Beach 🏖️ access.

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is CA $157
CA $687 total
includes taxes & fees
Feb 22 - Feb 23
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 reviews)
"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "
United States
Jennifer A.
The price is CA $260
CA $582 total
includes taxes & fees
Feb 10 - Feb 11
Entire Vacation Home in Waterford Connecticut

Stylish Modern Stay Steps from the Ocean

Stylish Modern Stay Steps from the Ocean
Clinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is CA $222
CA $460 total
includes taxes & fees
Feb 14 - Feb 15
Stylish Modern Stay Steps from the Ocean

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (43 reviews)
"Great property, would stay here again."
United States
charles b.
The price is CA $313
CA $667 total
includes taxes & fees
Feb 10 - Feb 11
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
United States
Doug F.
The price is CA $342
CA $704 total
includes taxes & fees
Feb 15 - Feb 16
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is CA $197
CA $703 total
includes taxes & fees
Feb 10 - Feb 11
Beachside Bliss w/ Game Room, Gym & Golf Green

Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
The price is CA $205
CA $492 total
includes taxes & fees
Feb 11 - Feb 12
Direct Lakefront - Stunning Views and Panoramic Sunsets

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"We loved our stay!"
United States
Deana L.
The price is CA $306
CA $748 total
includes taxes & fees
Feb 10 - Feb 11
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (109 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is CA $163
CA $250 total
includes taxes & fees
Feb 10 - Feb 11
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Lakeside cottage ON the water with beautiful views up the lake!

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (193 reviews)
"It was just wonderful!"
United States
Anonymous traveller
The price is CA $163
CA $387 total
includes taxes & fees
Feb 12 - Feb 13
Lakeside cottage ON the water with beautiful views up the lake!

The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's
Oakdale,
10.0 out of 10, Exceptional, (4 reviews)
"Host was extremely nice and responsive. Cottage is so cute I can't wait to come back in the summer! Nice and private little place and adorable goats! If you're looking for a quiet, cute little getaway this is the place to go! Thank you Thomas for the hospitality!!"
United States
Sharon O.
The price is CA $117
CA $162 total
includes taxes & fees
Feb 10 - Feb 11
The Tiny Cottage at Clem & Clyde's

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2
Stonington
10.0 out of 10, Exceptional, (5 reviews)
"Great stay with friends! "
United States
Danielle V.
The price is CA $135
CA $328 total
includes taxes & fees
Feb 11 - Feb 12
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

Lakeside cottage overhanging the water, beautiful window views across the lake

Lakeside cottage overhanging the water, beautiful window views across the lake
Ledyard
9.8 out of 10, Exceptional, (221 reviews)
"This lakeside cottage did not disappoint! It was just as advertised: we enjoyed a fire pit on the top deck and the hot tub on the bottom deck. The views were beautiful! And it was perfectly located to Foxwoods, Mystic, Stonington, Groton, etc. We'll definitely be back! "
United States
Elizabeth O.
The price is CA $133
CA $329 total
includes taxes & fees
Feb 10 - Feb 11
Lakeside cottage overhanging the water, beautiful window views across the lake

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is CA $123
CA $286 total
includes taxes & fees
Feb 16 - Feb 17
The Stern at Soundview · Beach+Ocean+Sunrise

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay! We were able to fit a pack and play for our 1 year old in the game room, which was a fun space. The fenced-in back yard was perfect for our dog. "
United States
Christine S.
The price is CA $208
CA $441 total
includes taxes & fees
Mar 1 - Mar 2
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Old Saybrook Hotel Reviews

Find out more about Old Saybrook

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Saybrook. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Old Saybrook?

Yes, there are vacation rentals in Old Saybrook close to Stay and Play LLC, or you can go with a more remote option if you're looking for a relaxing stay. Visitors like the popular beaches and shops in Old Saybrook. Allow some time to check out the spas during your trip.

What are some of the best vacation home rentals in Old Saybrook?

Charming Historic House in Downtown Mystic: This vacation home rental outside of Old Saybrook is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Old Saybrook?

Choose from 50 Expedia vacation rentals in Old Saybrook for a memorable vacation.

What’s there to see and do in Old Saybrook?

Family-friendly attractions include Stay and Play LLC and Saybrook Country Barn, whereas Harvey's Beach and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Katharine Hepburn Cultural Arts Center and Chalker Beach.

What’s a vacation rental in Old Saybrook like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Saybrook. Vacation rentals offer extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.