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

Holiday Homes in Old Saybrook

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is AU$633
includes taxes & fees
18 Oct - 19 Oct
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 AU$807
includes taxes & fees
21 Oct - 22 Oct
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, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AU$785
includes taxes & fees
20 Oct - 21 Oct
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 AU$1,953
includes taxes & fees
12 Nov - 13 Nov
Charming beach home, complete with pool & cozy guest house!
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (64 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 AU$395
includes taxes & fees
28 Oct - 29 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

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 AU$698
includes taxes & fees
9 Nov - 10 Nov
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A sandy beach with a wooden fence in the foreground and a clear sky with clouds in the background.

7. 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, (27 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 AU$348
includes taxes & fees
28 Oct - 29 Oct
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.

8. 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 AU$632
includes taxes & fees
15 Nov - 16 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

9. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (56 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 AU$369
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

10. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$367
includes taxes & fees
17 Nov - 18 Nov
Aqua Vista
A wooden deck with a round table and chairs overlooking a lake, surrounded by lush greenery.

11. 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 AU$838
includes taxes & fees
16 Nov - 17 Nov
Lakeside Bliss
A modern living room with a large wooden dining table, a stone fireplace, a sofa, and a view of a lake through large windows.

12. 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 AU$508
includes taxes & fees
9 Nov - 10 Nov
Thames River Cottage · Near Casinos - USCGA
A beach with people relaxing, a pier extending into the water, and a clear sky.

13. 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, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is AU$535
includes taxes & fees
8 Nov - 9 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A two-story house with a porch and a wooden picnic table in the front yard.

14. 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, (192 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is AU$374
includes taxes & fees
17 Nov - 18 Nov
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.

15. 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 AU$435
includes taxes & fees
26 Oct - 27 Oct
American Beech in Greenport - Petite King Room 7
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 AU$626
includes taxes & fees
16 Nov - 17 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 AU$602
includes taxes & fees
9 Nov - 10 Nov
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
A two-story house with a covered patio area, a front door, and a mailbox.

18. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (72 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
The price is AU$390
includes taxes & fees
27 Oct - 28 Oct
Cozy, comfy,quiet &close to casinos
A compact living room with a gray sofa, a coffee table, and a black TV stand.

19. 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 AU$516
includes taxes & fees
5 Nov - 6 Nov
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Saybrook Hotel Reviews

Grand Pequot Tower at Foxwoods

Grand Pequot Tower at Foxwoods

10/10 Excellent
"Wonderful stay!!!"
Renee 2-night trip
Posted 1 hour ago
Grand Pequot Tower at Foxwoods

Find out more about Old Saybrook

Old Saybrook Holiday Homes information

Number of reviews
809
Accommodation
852 Holiday Homes
Lowest Price
AU$348
Highest Price
AU$1,953