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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Old Saybrook cottages

Exterior

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, 56, (56 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $167
CA $320 total
includes taxes & fees
Oct 6 - Oct 7
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

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, 28, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is CA $243
CA $449 total
includes taxes & fees
Oct 7 - Oct 8
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

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, 8, (8 reviews)
"Great host and property"
United States
Kevin K.
The price is CA $303
CA $752 total
includes taxes & fees
Sep 15 - Sep 16
Adorable Cottage with Cottage porch, walk to water & town
Exterior

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, 1, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is CA $206
CA $464 total
includes taxes & fees
Sep 28 - Sep 29
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Exterior

5. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, 95, (95 reviews)
"Great cottage on the Sound!"
United States
David S.
The price is CA $874
CA $1,363 total
includes taxes & fees
Sep 28 - Sep 29
Direct waterfront renovated cottage.
Balcony

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, 54, (54 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $416
CA $475 total
includes taxes & fees
Sep 16 - Sep 17
North Fork Resort
Cottage (1 Bedroom) | Interior

7. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
3.0 star property
Montville
10.0 out of 10, 3, (3 reviews)
"The pool was amazing, the host was great, very accessible and the property was prisine. The views alone made us immediately want to come back. Very clean and well stocked. "
United States
agata
The price is CA $229
CA $527 total
includes taxes & fees
Sep 16 - Sep 17
Private Guest House w/ Deck + Spectacular Views!
Terrace/patio

8. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
Montville
10.0 out of 10, 41, (41 reviews)
"I had a pleasant stay, the house is very clean, well-equipped, and the peace and quiet were perfect. I commend the owner."
United States
Faniola O.
The price is CA $171
CA $529 total
includes taxes & fees
Sep 16 - Sep 17
Private Guest House w/ Deck + Spectacular Views!
Exterior

9. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, 11, (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 CA $160
CA $211 total
includes taxes & fees
Oct 6 - Oct 7
The Tiny Cottage & Mini Farm
Exterior

10. 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, 33, (33 reviews)
"The home is very well kept and is in a wonderful location. We enjoyed it a great deal and would go back in a heart beat."
United States
Chrissy R.
The price is CA $291
CA $557 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Private kitchen

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

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
8.0 out of 10, 2, (2 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 CA $243
CA $450 total
includes taxes & fees
Sep 15 - Sep 16
Privet Farm cottage with AC and Deck in charming Salem Connecticut
Terrace/patio

12. 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, 8, (8 reviews)
"Very nice little place. Quite, clean and only minutes from Mystic and downtown New London."
United States
Nicholas C.
The price is CA $277
CA $625 total
includes taxes & fees
Oct 5 - Oct 6
115 Rose Cottage with 2 bedroom walk to Groton Bay
Terrace/patio

13. 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, 24, (24 reviews)
"Fantastic place to stay. "
United States
Cathy M.
The price is CA $415
CA $531 total
includes taxes & fees
Sep 21 - Sep 22
Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
Property grounds

14. 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, 234, (234 reviews)
"wonderful place to stay. the pond is beautiful. plenty to do nearby "
United States
Mike
The price is CA $332
CA $558 total
includes taxes & fees
Sep 27 - Sep 28
Lakeside cottage overhanging the water, beautiful window views across the lake
Terrace/patio

15. 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, 13, (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 CA $304
CA $378 total
includes taxes & fees
Sep 15 - Sep 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!
Terrace/patio

16. 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, 1, (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 CA $763
CA $1,336 total
includes taxes & fees
Oct 6 - Oct 7
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
House (4 Bedrooms) | Interior

17. 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
The price is CA $548
CA $1,118 total
includes taxes & fees
Oct 5 - Oct 6
Groton Home < 1 Mi to Beach on Long Island Sound!
Marina

18. 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
The price is CA $375
CA $617 total
includes taxes & fees
Sep 20 - Sep 21
Pet friendly king-bed suite in historic downtown Mystic carriage house
Exterior

19. 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, 19, (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 CA $347
CA $445 total
includes taxes & fees
Sep 22 - Sep 23
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
Interior

20. 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, 7, (7 reviews)
"We loved the place. Will definitely stay there again! "
United States
Kristen C.
The price is CA $485
CA $593 total
includes taxes & fees
Sep 27 - Sep 28
Harbor View Landing Mystic, CT - The Martha's Vineyard 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
"When I checked in the woman was very nice. She asked me if I wanted a higher floor which I did. She gave me a key to room on the ground floor which I entered and figured it was a mistake but oh well. The a/c didn’t seem to be working so I did go back to the desk to tell her and mention I think she gave me the wrong room. She was very nice, apologized and gave me a key to a second floor room. This room was much nicer and cleaner. The bed was comfortable and all was fine. The breakfast selection was what you would expect with a few more options than usual. There is a coffee maker in the room but nowhere to get just plain hot water at night. They could keep a thermos where they keep ice water during the day. When I checked out, there was no one at the desk so I waited a bit then called out hello and the book keeper came to check me out. Housekeepers were nice and greeted you as you passed them in the hallway. Very quiet and courtyard garden was nice. Would stay again."
carolyn 1-night trip
Posted less than an hour ago
Two Trees Inn

Find out more about Old Saybrook

Old Saybrook Cottages information

Number of reviews
509
Accommodation
226 Cottages
Lowest Price
CA $211
Highest Price
CA $1,363

Frequently asked questions

How much do cottages in Old Saybrook cost?
Expect to pay between CA $211 and CA $1,363 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.

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