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 vacation 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, (14 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ￥35,073
￥71,240 total
includes taxes & fees
Oct 1 - Oct 2
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 ￥45,334
￥83,695 total
includes taxes & fees
Sep 30 - Oct 1
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

3. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥26,067
￥74,233 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥42,076
￥100,845 total
includes taxes & fees
Oct 27 - Oct 28
Beachside Bliss w/ Game Room, Gym & Golf Green
A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

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

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (7 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 ￥17,853
￥53,939 total
includes taxes & fees
Sep 30 - Oct 1
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A stone pier leading to a beach with houses in the background.

6. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (61 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is ￥17,709
￥41,435 total
includes taxes & fees
Oct 6 - Oct 7
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A two-story house with a covered patio area, a front door, and a mailbox.

7. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (69 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
The price is ￥18,134
￥42,104 total
includes taxes & fees
Sep 30 - Oct 1
Cozy, comfy,quiet &close to casinos
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, (26 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 ￥13,742
￥36,692 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
A living room with a fireplace, a grey armchair, and a large window.

9. 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 ￥26,574
￥68,650 total
includes taxes & fees
Sep 30 - Oct 1
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A modern living room with a large wooden dining table, a stone fireplace, a sofa, and a view of a lake through large windows.

10. Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (3 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is ￥23,127
￥54,389 total
includes taxes & fees
Oct 1 - Oct 2
Thames River Cottage · Near Casinos - USCGA
A compact living room with a gray sofa, a coffee table, and a black TV stand.

11. Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (15 reviews)
"great place to stay"
United States
christopher
The price is ￥20,463
￥48,561 total
includes taxes & fees
Oct 4 - Oct 5
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
A two-story house with a porch and a wooden picnic table in the front yard.

12. 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, (190 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is ￥17,473
￥41,344 total
includes taxes & fees
Sep 30 - Oct 1
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.

13. 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 ￥31,299
￥45,645 total
includes taxes & fees
Oct 4 - Oct 5
American Beech in Greenport - Petite King Room 7
A beach with people relaxing, a pier extending into the water, and a clear sky.

14. 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, (32 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥27,603
￥62,625 total
includes taxes & fees
Oct 12 - Oct 13
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A modern kitchen with a central island, built-in appliances, and a dining area with a long table and chairs.

15. 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 ￥27,972
￥70,062 total
includes taxes & fees
Oct 5 - Oct 6
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
A covered porch with wooden chairs and a bench, overlooking a street with cars and houses.

16. Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Mystic River Historic District
9.8 out of 10, Exceptional, (178 reviews)
"Great location "
United States
Brian S.
The price is ￥19,723
￥43,733 total
includes taxes & fees
Oct 1 - Oct 2
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

17. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (47 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,806
￥47,622 total
includes taxes & fees
Oct 12 - Oct 13
Aqua Vista
A wooden deck with a round table and chairs overlooking a lake, surrounded by lush greenery.

18. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (31 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 ￥56,526
￥81,337 total
includes taxes & fees
Oct 6 - Oct 7
Lakeside Bliss
A wooden deck with a white staircase leading to a covered area with a table and chairs.

19. Winner's Getaway - 2mi to Mohegan Sun

Winner's Getaway - 2mi to Mohegan Sun
Westside Norwich
10.0 out of 10, Exceptional, (13 reviews)
"Close to casino, would recommend"
United States
Joe M.
The price is ￥25,689
￥75,978 total
includes taxes & fees
Sep 30 - Oct 1
Winner's Getaway - 2mi to Mohegan Sun
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

20. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥22,806
￥47,622 total
includes taxes & fees
Oct 25 - Oct 26
The SandPiper
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

10/10 Excellent
"All good"
Daniel 2-night trip
Posted 1 hour ago
Two Trees Inn

Find out more about Old Saybrook

Old Saybrook Vacation Homes information

Number of reviews
928
Accommodation
861 Vacation Homes
Lowest Price
￥36,692
Highest Price
￥100,845