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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Old Saybrook

Sweet Cottage in Beach Community
Fridge, microwave, oven, stovetop

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (7)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
On the beach

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Updated '50's Cottage 5 mins to the beach with indoor and outdoor entertainment!
Fridge, microwave, oven, stovetop

Updated '50's Cottage 5 mins to the beach with indoor and outdoor entertainment!

10.0 out of 10, Exceptional, (20)
"Had a wonderful stay at this adorable cottage home! The home was clean and spacious. It had great access to everything we needed!"
The price is AED 992
AED 1,226 total
includes taxes & fees
18 Jul - 19 Jul
Updated '50's Cottage 5 mins to the beach with indoor and outdoor entertainment!
Lakeside cottage overhanging the water, beautiful window views across the lake
Outdoor dining

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

9.8 out of 10, Exceptional, (205)
"Great cottage right on the water! Cute swings on the deck! The hot tub was great! "
Lakeside cottage overhanging the water, beautiful window views across the lake
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
On the beach, sun loungers, beach towels

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

9.8 out of 10, Exceptional, (71)
"We stayed at this property last year and again this year. You can’t beat the location and the house is perfect for a group of family or friends. We had a lovely time and look forward to another stay in the future!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Cozy Home near private beach , close to New Haven area colleges Hospitals
Property grounds

Cozy Home near private beach , close to New Haven area colleges Hospitals

9.6 out of 10, Exceptional, (64)
"Exactly as advertised, very friendly and accommodating. "
Cozy Home near private beach , close to New Haven area colleges Hospitals
Go Jump in the Lake!

Go Jump in the Lake!

10.0 out of 10, Exceptional, (141)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!
Spacious 2BR Norwich Cottage
Outdoor dining

Spacious 2BR Norwich Cottage

9.6 out of 10, Exceptional, (19)
"We had a great time. Our new puppy loved walking the grounds (on leash inside and out). Very private and close to all we wanted to see...seaport, restaurants, casinos. Loved our stay there. Thanks for everything."
Spacious 2BR Norwich Cottage
Lovely Cottage in the Heart of Long Island Wine country
Beach

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (25)
"we had such a fun weekend out in southold! Cottage was perfect for us for a cold rainy weekend. Everything was so close to the house. Will definitely be back in the summer!"
Lovely Cottage in the Heart of Long Island Wine country
Charming 3-bedroom cottage short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

10.0 out of 10, Exceptional, (1)
"We recently stayed here and have to say the owners went above and beyond our expectations!!! The home was just as described in the listing, very clean, organized and is in a great location. I would definitely stay here again. I would absolutely recommend this home for your next stay in CT.Thank you Karen for everything!!!"
Charming 3-bedroom cottage short walk to Chalker Beach
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (16)
"My wife and I, and our little dog, had a great experience staying at the Yellow Cottage. For our needs, it was perfectly located. It's on a busy street, but the traffic noises wound down at night. Much nicer than the hotels in the area."
Historic Whitneyville Cottage
Charming secluded island cottage
Outdoor dining

Charming secluded island cottage

Charming secluded island cottage
Lakeside cottage ON the water with beautiful views up the lake!
Property grounds

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

9.8 out of 10, Exceptional, (181)
"Super cute. We enjoyed the views and the hut tub. "
Lakeside cottage ON the water with beautiful views up the lake!
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (26)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AED 575
AED 1,160 total
includes taxes & fees
26 Jul - 27 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Privately Located Beach Cottage Getaway
Beach nearby, beach towels

Privately Located Beach Cottage Getaway

9.6 out of 10, Exceptional, (50)
"Quaint and close to beach, shopping and restaurants"
Privately Located Beach Cottage Getaway
Historic cottage in Deep River, CT
Property grounds

Historic cottage in Deep River, CT

10.0 out of 10, Exceptional, (1)
"Wonderful stay. Charming and perfect. "
The price is AED 661
AED 1,280 total
includes taxes & fees
20 Jul - 21 Jul
Historic cottage in Deep River, CT
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

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

10.0 out of 10, Exceptional, (15)
"Robin was a great resource about the area. Her property was amazing the cottage was fantastic. Very comfortable and clean. We had a relaxing stay and a great time. We would love to go back again and again!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Waterfront Pool Cottage Watch Hill Misquamicut Westerly Beaches
Outdoor pool, a heated pool

Waterfront Pool Cottage Watch Hill Misquamicut Westerly Beaches

10.0 out of 10, Exceptional, (17)
"We had a great family vacation at this property. Ronnie and his family are great hosts. Unit has plenty of privacy. Place is immaculate, beautifully designed. Thanks for having us! "
Waterfront Pool Cottage Watch Hill Misquamicut Westerly Beaches
Private Guest House w/ Deck + Spectacular Views!
Property grounds

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (30)
"Great place. Great host"
Private Guest House w/ Deck + Spectacular Views!
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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Frequently asked questions

How much do cottages in Old Saybrook cost?
Expect to pay between AED 575 and AED 992 per night for cottages in Old Saybrook. No matter your budget, a terrific stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Old Saybrook?
Claim your vacation time and pick from 230 cottages in Old Saybrook. Yearning for a place where you can get in touch with nature? Expedia will help you find your ideal stay in only a click or two.
Why book your cottage in Old Saybrook with Expedia?
Expedia has some terrific cottages in Old Saybrook, so start planning for an unforgettable vacation on nature's doorstep. If you have a fixed budget, click on how much you're willing to spend and your preferred property star rating. Or, use our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect pad whatever your getaway looks like.