Old Saybrook Holiday Homes from €213: Search Top House Rentals

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

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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.

Old Saybrook

Becky W.

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

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

Westbrook Center

Donovan V.

includes taxes & fees

18 Oct - 19 Oct

A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

3. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Saybrook Manor

Alexis L.

includes taxes & fees

21 Oct - 22 Oct

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

Westbrook

Shannon G.

includes taxes & fees

20 Oct - 21 Oct

A modern living room with a large TV, white cabinetry, and a view of the outdoors.

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

Clinton

Juliana A.

A stone pier leading to a beach with houses in the background.

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

Old Lyme

Emily M.

includes taxes & fees

18 Oct - 19 Oct

A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

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

East Lyme

Sarah G.

includes taxes & fees

9 Nov - 10 Nov

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

New London

Alicia W.

includes taxes & fees

26 Oct - 27 Oct

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

Waterford

Elaine A.

includes taxes & fees

9 Nov - 10 Nov

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

10. The SandPiper

Pipes Cove

Julian V.

includes taxes & fees

10 Nov - 11 Nov

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

11. Aqua Vista

Pipes Cove

Kerri L.

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with a round table and chairs overlooking a lake, surrounded by lush greenery.

12. Lakeside Bliss

East Lyme

Brenda M.

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a large wooden dining table, a stone fireplace, a sofa, and a view of a lake through large windows.

13. Thames River Cottage · Near Casinos - USCGA

Montville

Bonnie H.

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

Pipes Cove

"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!"

Nino

includes taxes & fees

12 Nov - 13 Nov