Old Saybrook Holiday Rentals

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Our top choices for Old Saybrook holiday rentals

9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is NZ$296
includes taxes & fees
30 Dec - 31 Dec
1-bedroom cottage with Grove Beach 🏖️ access.

Mobile Home in East Lyme

Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is NZ$361
includes taxes & fees
30 Dec - 31 Dec
Cozy Lakefront Tiny House

Mobile Home in East Lyme

Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (3)
"this place was amazing i would come again"
United States
Tatyanna R.
The price is NZ$380
includes taxes & fees
7 Jan - 8 Jan 2026
Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (1)
"The home was very clean and welcoming."
United States
Michelle M.
The price is NZ$632
includes taxes & fees
30 Dec - 31 Dec
Charming 2-bedroom house with WiFi, AC in lovely Waterford
2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$804
includes taxes & fees
5 Jan - 6 Jan 2026
Beachside Bliss w/ Game Room, Gym & Golf Green

Apartment in Clinton

Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is NZ$443
includes taxes & fees
30 Dec - 31 Dec
Shoreline Oasis
2.0 star property
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
The price is NZ$887
includes taxes & fees
11 Jan - 12 Jan 2026
LONG-TERM Winter by the Ocean and Ski Resort 30 mins away

Holiday Home in Westbrook Center

Adorable Cottage, 5 min walk to water & town
9.4 out of 10, Exceptional, (15)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$717
includes taxes & fees
30 Dec - 31 Dec
Adorable Cottage, 5 min walk to water & town
2.0 star property
9.0 out of 10, Wonderful, (2)
"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$731
includes taxes & fees
30 Dec - 31 Dec
Entire Vacation Home in Waterford Connecticut
10.0 out of 10, Exceptional, (1)
"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$578
includes taxes & fees
11 Jan - 12 Jan 2026
Stylish Modern Stay Steps from the Ocean
9.6 out of 10, Exceptional, (133)
"We loved our stay!"
United States
Deana L.
The price is NZ$991
includes taxes & fees
12 Jan - 13 Jan 2026
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (95)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
United States
Keven
The price is NZ$313
includes taxes & fees
4 Jan - 5 Jan 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
10.0 out of 10, Exceptional, (2)
"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$221
includes taxes & fees
1 Jan - 2 Jan 2026
The Tiny Cottage at Clem & Clyde's
9.8 out of 10, Exceptional, (192)
"There were stunning views, it was very relaxing, and we had excellent communication with the host. We couldn’t be happier, it was perfect! Kayaking was the best part. Plenty to see and do in the area as well."
United States
Heather S.
The price is NZ$462
includes taxes & fees
5 Jan - 6 Jan 2026
Lakeside cottage ON the water with beautiful views up the lake!
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is NZ$331
includes taxes & fees
10 Jan - 11 Jan 2026
The Stern at Soundview · Beach+Ocean+Sunrise
9.8 out of 10, Exceptional, (220)
"Very comfortable, easy to get to and had everything you could need in a house rental! "
United States
Anna K.
The price is NZ$441
includes taxes & fees
5 Jan - 6 Jan 2026
Lakeside cottage overhanging the water, beautiful window views across the lake
10.0 out of 10, Exceptional, (4)
"We enjoyed our stay. The apartment is in excellent condition."
United States
Marcell
The price is NZ$367
includes taxes & fees
12 Jan - 13 Jan 2026
Stevedore Landing-#3 · walk downtown Mystic · train · aquarium
10.0 out of 10, Exceptional, (27)
"Everything was perfect! Great location, easy check in/out, great amenities in room, and super comfy bed. "
United States
Paul S.
The price is NZ$338
includes taxes & fees
3 Jan - 4 Jan 2026
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
9.8 out of 10, Exceptional, (16)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is NZ$437
includes taxes & fees
4 Jan - 5 Jan 2026
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
10.0 out of 10, Exceptional, (6)
"Place is nice would stay again "
United States
nic
The price is NZ$635
includes taxes & fees
5 Jan - 6 Jan 2026
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
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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Top Old Saybrook Hotel Reviews

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$208 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 Saybrook Country Barn, 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?

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages: This holiday home rental outside of Old Saybrook has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Old Saybrook?

Choose from 54 Expedia holiday rentals in Old Saybrook for a memorable holiday.

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

Family-friendly attractions include Saybrook Country Barn and Stay and Play LLC, 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.