A rocky beach with large boulders and the ocean in the background.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Old Saybrook cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

1. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥17,758
￥34,921 total
includes taxes & fees
Oct 5 - Oct 6
1-bedroom cottage with Grove Beach 🏖️ access.
A white cottage with a front door, a garage, and a small porch with a potted plant.

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is ￥24,861
￥46,941 total
includes taxes & fees
Oct 13 - Oct 14
The gardners Cottage 1 mile from long Island Sound - pet friendly
A two-story house with a porch, multiple windows, and a front door.

3. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and comfortable"
United States
Francine F.
The price is ￥32,675
￥82,745 total
includes taxes & fees
Oct 5 - Oct 6
Adorable Cottage with Cottage porch, walk to water & town
A two-story house with a porch, a mailbox, and a lawn.

4. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is ￥24,861
￥56,965 total
includes taxes & fees
Oct 20 - Oct 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

5. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥39,249
￥44,843 total
includes taxes & fees
Oct 7 - Oct 8
North Fork Resort
A small white house with black shutters, a porch, and a red barn in the background.

6. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is ￥16,337
￥21,945 total
includes taxes & fees
Oct 6 - Oct 7
The Tiny Cottage & Mini Farm
A small, single-story house with a white porch and a wooden front door.

7. 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, (33 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is ￥33,149
￥63,377 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
A small white house with a green door, two wicker chairs with red cushions, and a welcome mat.

8. 115 Rose Cottage with 2 bedroom walk to Groton Bay

115 Rose Cottage with 2 bedroom walk to Groton Bay
Groton
8.8 out of 10, Excellent, (8 reviews)
"Very nice little place. Quite, clean and only minutes from Mystic and downtown New London."
United States
Nicholas C.
The price is ￥28,413
￥67,323 total
includes taxes & fees
Nov 3 - Nov 4
115 Rose Cottage with 2 bedroom walk to Groton Bay
A covered outdoor deck with wicker furniture, a ceiling fan, and a view of a park.

9. Groton Home < 1 Mi to Beach on Long Island Sound!

Groton Home < 1 Mi to Beach on Long Island Sound!
3.0 star property
Groton
Groton Home < 1 Mi to Beach on Long Island Sound!
A single-story house with a grey exterior, a front door, and two windows.

10. 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, (10 reviews)
"Great stay with friends! "
United States
Danielle V.
The price is ￥25,430
￥51,149 total
includes taxes & fees
Nov 2 - Nov 3
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2
A dining area with a round wooden table surrounded by six white chairs with dark cushions. A potted plant with green foliage and pink flowers is placed in the center.

11. Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
8.8 out of 10, Excellent, (3 reviews)
"We enjoyed our stay at the cottage. It was perfect for traveling with our dogs very comfortable, nice and quiet."
United States
Ed B.
The price is ￥30,781
￥55,169 total
includes taxes & fees
Oct 13 - Oct 14
Privet Farm cottage with AC and Deck in charming Salem Connecticut
A small, single-story building with a red door and windows, a covered picnic table, and a barbecue grill outside.

12. 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, (211 reviews)
"Sweet, cozy and clean. We had a nice time fishing, spotted a wide variety of birds, and enjoyed a few rounds of croquet. The lake was peaceful and quiet but is only a few minutes from the Foxwoods complex for shopping, dining, casino and shows. Thanks for a great stay!"
United States
Marcy P.
The price is ￥26,203
￥54,285 total
includes taxes & fees
Nov 1 - Nov 2
Lakeside cottage ON the water with beautiful views up the lake!
A deck with a grill, a glass table, and kayaks by a lake.

13. 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, (237 reviews)
"The kids had a blast fishing off the dock, very clean and comfortable"
United States
katlyn w.
The price is ￥25,256
￥51,064 total
includes taxes & fees
Nov 3 - Nov 4
Lakeside cottage overhanging the water, beautiful window views across the lake
A deck with a gray sofa, a wooden chair, and a metal fire pit.

14. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is ￥84,134
￥149,506 total
includes taxes & fees
Nov 3 - Nov 4
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A covered outdoor seating area with a view of a lake and dock.

15. Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage

Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
West Mystic
10.0 out of 10, Exceptional, (24 reviews)
"Fantastic place to stay. "
United States
Cathy M.
The price is ￥51,301
￥66,415 total
includes taxes & fees
Oct 12 - Oct 13
Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
A covered outdoor seating area with wicker furniture, a wooden table, and a bottle of wine.

16. Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!

Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
Ledyard
10.0 out of 10, Exceptional, (13 reviews)
"My husband and I stayed in the cottage with our fur baby and it was perfect. The cottage was very comfortable and very private."
United States
Kim S.
The price is ￥34,143
￥42,318 total
includes taxes & fees
Nov 2 - Nov 3
Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
A two-story house with a front porch, a white picket fence, and a mailbox.

17. Pet friendly king-bed suite in historic downtown Mystic carriage house

Pet friendly king-bed suite in historic downtown Mystic carriage house
Mystic River Historic District
8.0 out of 10, Very good, (1 review)
"The location was perfect for our needs. In town for a wedding and it was central to the venues and close to downtown. Nice neighborhood, felt safe."
United States
Carolyn G.
The price is ￥42,620
￥70,362 total
includes taxes & fees
Oct 19 - Oct 20
Pet friendly king-bed suite in historic downtown Mystic carriage house
A small, single-story building with a dark roof and light gray siding, labeled "THE COVE".

18. Harbor View Landing, Mystic CT - The Cove Waterfront Cottage

Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
West Mystic
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful time, great place which was like a small resort. Beautiful views and it was quiet and so peaceful there. We’re looking forward to staying again."
United States
Michael V.
The price is ￥35,516
￥45,421 total
includes taxes & fees
Oct 5 - Oct 6
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
A deck with two Adirondack chairs and a small table, overlooking a marina with boats and a clear sky.

19. Harbor View Landing Mystic, CT - The Martha's Vineyard Waterfront Cottage

Harbor View Landing Mystic, CT - The Martha's Vineyard Waterfront Cottage
West Mystic
10.0 out of 10, Exceptional, (7 reviews)
"We loved the place. Will definitely stay there again! "
United States
Kristen C.
The price is ￥62,982
￥81,427 total
includes taxes & fees
Oct 19 - Oct 20
Harbor View Landing Mystic, CT - The Martha's Vineyard Waterfront Cottage
A house with a stone foundation, a sloped roof, and a view of a lake.

20. Harbor View Landing Mystic, CT - The Nantucket Waterfront Cottage

Harbor View Landing Mystic, CT - The Nantucket Waterfront Cottage
West Mystic
10.0 out of 10, Exceptional, (5 reviews)
"The cottage was beautifully decorated, cozy and made our stay very comfortable. The scenery was spectacular. We will definitely be going back!"
United States
Anonymous traveler
The price is ￥47,197
￥61,064 total
includes taxes & fees
Oct 6 - Oct 7
Harbor View Landing Mystic, CT - The Nantucket Waterfront Cottage
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

Two Trees Inn

Two Trees Inn

8/10 Good
"Clean and comfortable great location"
Frank 2-night trip
Posted less than an hour ago
Two Trees Inn

Find out more about Old Saybrook

Old Saybrook Cottages information

Number of reviews
650
Accommodation
226 Cottages
Lowest Price
￥21,945
Highest Price
￥149,506

Frequently asked questions

How much do cottages in Old Saybrook cost?
Expect to pay between ￥21,945 and ￥149,506 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 226 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.
How can I find cheap cottages in Old Saybrook?
With Expedia's helpful filter tool, comparing cheap cottages in Old Saybrook is easy. To find accommodations that'll make your bank balance smile, tailor your search results by budget, star rating and amenities.
What is there to do in Old Saybrook near my cottage?
You'll find loads of terrific things to sink your teeth into in Old Saybrook. Make tracks to major attractions like Harvey's Beach, Katharine Hepburn Cultural Arts Center and Chalker Beach. Essex Saybrook Antique Village Shopping Center, Crystal Lake Town Park and Saybrook Country Barn are other highlights.