Old Saybrook Holiday Rentals

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Our top choices for Old Saybrook holiday rentals

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 NZ$298
includes taxes & fees
23 Feb - 24 Feb
1-bedroom cottage with Grove Beach 🏖️ access.

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 NZ$367
includes taxes & fees
3 Mar - 4 Mar
Cozy Lakefront Tiny House

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 NZ$592
includes taxes & fees
14 Feb - 15 Feb
Charming 2-bedroom house with WiFi, AC in lovely Waterford

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 NZ$841
includes taxes & fees
15 Feb - 16 Feb
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

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 NZ$357
includes taxes & fees
24 Feb - 25 Feb
Lakefront Boho 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 NZ$579
includes taxes & fees
1 Mar - 2 Mar
The gardners Cottage 1 mile from long Island Sound - pet friendly

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 NZ$690
includes taxes & fees
14 Feb - 15 Feb
Entire Vacation Home in Waterford Connecticut

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 NZ$846
includes taxes & fees
18 Feb - 19 Feb
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

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 NZ$582
includes taxes & fees
15 Feb - 16 Feb
Stylish Modern Stay Steps from the Ocean

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 NZ$889
includes taxes & fees
16 Feb - 17 Feb
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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 NZ$808
includes taxes & fees
25 Feb - 26 Feb
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
The price is NZ$609
includes taxes & fees
17 Feb - 18 Feb
Direct Lakefront - Stunning Views and Panoramic Sunsets

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 NZ$880
includes taxes & fees
17 Feb - 18 Feb
Beachside Bliss w/ Game Room, Gym & Golf Green

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, (111 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 NZ$269
includes taxes & fees
17 Feb - 18 Feb
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's
Oakdale,
10.0 out of 10, Exceptional, (5 reviews)
"Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! "
United States
jeff
The price is NZ$196
includes taxes & fees
16 Feb - 17 Feb
The Tiny Cottage at Clem & Clyde's

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 NZ$347
includes taxes & fees
15 Feb - 16 Feb
The Stern at Soundview · Beach+Ocean+Sunrise

Luxe Living! Apt 1 Mi to West Haven Medical Center

Luxe Living! Apt 1 Mi to West Haven Medical Center
3.0 star property
West Haven
The price is NZ$592
includes taxes & fees
15 Feb - 16 Feb
Luxe Living! Apt 1 Mi to West Haven Medical Center

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (7 reviews)
"A beautiful place to stay! Comfortable, cozy and clean. All amenities and the surprise dessert was awesome! We will definitely be back!"
United States
Tammy Z.
The price is NZ$357
includes taxes & fees
16 Feb - 17 Feb
A Mystic Stay as Sweet as Apple Pie!

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (172 reviews)
"Perfect for our overnight needs."
United States
Kathleen C.
The price is NZ$406
includes taxes & fees
12 Mar - 13 Mar
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay! The host was welcoming and attentive. Great attention to detail with the room- everything we needed and more. The property was charming. We enjoyed our stay!"
United States
Christine P.
The price is NZ$347
includes taxes & fees
17 Feb - 18 Feb
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
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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Find out more about Old Saybrook

Everything you need to know about Old Saybrook holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Old Saybrook holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Saybrook holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Old Saybrook holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Saybrook. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Saybrook holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Old Saybrook holiday rentals we have selected for you start as low as NZ$269 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Old Saybrook rentals

At Expedia, we put the best Old Saybrook holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Old Saybrook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Saybrook holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Saybrook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Old Saybrook?

Yes, there are holiday rentals in Old Saybrook close to Stay and Play LLC, or you can select a more secluded 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 holiday rentals that Old Saybrook has to offer?

Charming Historic House in Downtown Mystic: This holiday home rental outside of Old Saybrook is located on a river, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Old Saybrook?

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

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 holiday rental in Old Saybrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Saybrook. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.