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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Old Saybrook holiday homes

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

1. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
The price is HK$1,646
HK$3,437 total
includes taxes & fees
8 Nov - 9 Nov
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

2. 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, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is HK$2,328
HK$4,304 total
includes taxes & fees
16 Nov - 17 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

3. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (4 reviews)
"Very lovely home! We very much enjoyed our stay and hope to be back again!"
United States
Morgan M.
The price is HK$1,406
HK$4,042 total
includes taxes & fees
10 Nov - 11 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
A modern living room with a large TV, white cabinetry, and a view of the outdoors.

4. Charming beach home, complete with pool & cozy guest house!

Charming beach home, complete with pool & cozy guest house!
Clinton
9.8 out of 10, Exceptional, (56 reviews)
"Beautiful, open and clean. Perfect for a family stay!"
United States
Juliana A.
The price is HK$5,236
HK$10,061 total
includes taxes & fees
12 Nov - 13 Nov
Charming beach home, complete with pool & cozy guest house!
A cozy living room with a sofa, a coffee table, and a dining area with chairs.

5. NEW private studio 1.1 miles to beach in East Lyme

NEW private studio 1.1 miles to beach in East Lyme
East Lyme
The price is HK$847
HK$1,068 total
includes taxes & fees
9 Nov - 10 Nov
NEW private studio 1.1 miles to beach in East Lyme
A tranquil beach with stunning ocean views.

6. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (8 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is HK$834
HK$2,560 total
includes taxes & fees
2 Dec - 3 Dec
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A living room with a fireplace, a grey armchair, and a large window.

7. Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is HK$1,146
HK$3,207 total
includes taxes & fees
9 Nov - 10 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A sandy beach with a wooden fence in the foreground and a clear sky with clouds in the background.

8. Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
New London
8.0 out of 10, Very good, (31 reviews)
"Good location, great price, communication always great with the host. Accommodations were clean, decorative and comfortable. Heat and air, family friendly, and neat. Will return and recommend to friends and family!"
United States
Alicia W.
The price is HK$684
HK$1,788 total
includes taxes & fees
9 Nov - 10 Nov
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
A wooden deck with a round table and chairs overlooking a lake, surrounded by lush greenery.

9. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (32 reviews)
"Lovely house - excellently equipped and fun decor. The owner was gracious and flexible and the location is beautiful. "
United States
Brenda M.
The price is HK$2,815
HK$4,113 total
includes taxes & fees
18 Nov - 19 Nov
Lakeside Bliss
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

10. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is HK$670
HK$1,805 total
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A beach with people relaxing, a pier extending into the water, and a clear sky.

11. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is HK$1,023
HK$2,727 total
includes taxes & fees
9 Nov - 10 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

12. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is HK$745
HK$1,899 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A modern living room with a sofa, a dining table, and a TV mounted on the wall.

13. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (75 reviews)
"All aspects of our stay were excellent!"
United States
Lori G.
The price is HK$698
HK$1,760 total
includes taxes & fees
9 Nov - 10 Nov
Cozy, comfy,quiet &close to casinos
A waterfront promenade with a concrete walkway, metal railing, and a sandy beach.

14. Coastal retreat, short walk to downtown!

Coastal retreat, short walk to downtown!
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"Check-in was very easy, kitchen was well stocked with basics, lots of towels and toiletries. Perfect space and location for our family weekend. Great host recommendations for places to visit as well!"
United States
Hannah R.
The price is HK$2,297
HK$3,327 total
includes taxes & fees
30 Nov - 1 Dec
Coastal retreat, short walk to downtown!
A modern living room with a large wooden dining table, a stone fireplace, a sofa, and a view of a lake through large windows.

15. Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (4 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is HK$1,034
HK$2,473 total
includes taxes & fees
9 Nov - 10 Nov
Thames River Cottage · Near Casinos - USCGA
A wooden pathway leading to a beach with scattered rocks and greenery.

16. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is HK$1,529
HK$3,358 total
includes taxes & fees
19 Nov - 20 Nov
Beach Block Hideaway
A modern kitchen with a central island, built-in appliances, and a dining area with a long table and chairs.

17. Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (12 reviews)
"Place is nice would stay again "
United States
nic
The price is HK$1,157
HK$3,087 total
includes taxes & fees
17 Nov - 18 Nov
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
A two-story house with a porch and a wooden picnic table in the front yard.

18. 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, (193 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is HK$784
HK$1,944 total
includes taxes & fees
7 Dec - 8 Dec
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
An outdoor dining area with hanging lights, palm trees, and a bar.

19. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is HK$1,560
HK$2,275 total
includes taxes & fees
10 Nov - 11 Nov
American Beech in Greenport - Petite King Room 7
A deck with wicker furniture and a view of a lake.

20. Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
9.8 out of 10, Exceptional, (27 reviews)
"Our host was amazing from the first day we booked through checkout. The property was so much fun and the views were incredible. No complaints!"
United States
Kristine E.
The price is HK$2,202
HK$5,235 total
includes taxes & fees
9 Nov - 10 Nov
Thames River Retreat · CT College+Casinos+USCGA
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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Old Saybrook and related destinations

Stroll the historic Main Street where local shops and seafood restaurants showcase New England's coastal charm. Kayak along the peaceful Connecticut River or relax at Harvey's Beach, where sunset views of Long Island Sound captivate visitors.

See all hotels in Old Saybrook
A coastal town with a lighthouse, houses, and a river.