Search Cottages in Southold

Start date: Check-in selected.
To Date
End date: Check-out

    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
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Featured Cottages in Southold and around

Exterior
1-bedroom cottage with Grove Beach 🏖️ access.
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (33)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is €157
includes taxes & fees
21 Oct - 22 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV
Hidden gem! Southampton beach cottage
Hidden gem! Southampton beach cottage
10.0 out of 10, Exceptional, (1)
The price is €395
includes taxes & fees
29 Oct - 30 Oct
Hidden gem! Southampton beach cottage
Exterior
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
9.6 out of 10, Exceptional, (38)
"Great property, would stay here again."
The price is €468
includes taxes & fees
20 Oct - 21 Oct
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Terrace/patio
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
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
The price is €506
includes taxes & fees
20 Oct - 21 Oct
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Exterior
Southampton cozy cottage by the beach
Southampton cozy cottage by the beach
10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is €396
includes taxes & fees
17 Oct - 18 Oct
Southampton cozy cottage by the beach
Exterior
Luxurious 3 BR Cottage w/ Ocean View Balcony
Luxurious 3 BR Cottage w/ Ocean View Balcony
10.0 out of 10, Exceptional, (3)
"Had a great weekend. Right on beach. Beautiful."
Luxurious 3 BR Cottage w/ Ocean View Balcony
Exterior
East End Escape
East End Escape
The price is €484
includes taxes & fees
17 Oct - 18 Oct
East End Escape
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 Southold Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Great stay overall. Only suggestion would be to put a light on the side of the building. "
Christopher 2-night trip
Posted 3 days ago
The Atlantic Hotel

Find out more about Southold

Southold Cottages information

Number of reviews
74
Accommodation
198 Cottages
Lowest Price
€157
Highest Price
€506

Frequently asked questions

Why book your cottage in Southold with Expedia?
Reserving a cottage in Southold is as easy as working out your travel dates and selecting your ideal place for a getaway in nature. From high-end retreats to low-cost properties and cottages that feature perks like a hot tub, Expedia has something for all traveller styles. As for unbeatable deals? We have them too!
How can I find cheap cottages in Southold?
A good way to spot cheap cottages in Southold is with Expedia's convenient filter tool. Refine your search by budget, star rating and amenities to secure unbeatable prices in just a few keystrokes.

Explore a world of travel with Expedia