Search Cottages in Southold

  • 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 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Southold cottages

Smart TV

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1 review)
The price is AED 202
AED 1,666 total
includes taxes & fees
29 Jan - 30 Jan
Seabreeze #3: Cozy Cottage by the beach
Exterior

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is AED 320
AED 690 total
includes taxes & fees
20 Jan - 21 Jan
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

Cottage in East Lyme

Beach Cottage, private beach and pass
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is AED 625
AED 1,467 total
includes taxes & fees
21 Jan - 22 Jan
Beach Cottage, private beach and pass
Terrace/patio

Cottage in Greenport

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is AED 1,102
AED 2,224 total
includes taxes & fees
5 Feb - 6 Feb
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Exterior

Cottage in Hampton Bays

Seabreeze #4: Charming Cottage Footsteps to the Beach
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is AED 202
AED 1,632 total
includes taxes & fees
20 Jan - 21 Jan
Seabreeze #4: Charming Cottage Footsteps to the Beach
Exterior

Cottage in Old Saybrook Center

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
9.6 out of 10, Exceptional, (42 reviews)
"Great property, would stay here again."
United States
charles b.
The price is AED 980
AED 1,966 total
includes taxes & fees
18 Jan - 19 Jan
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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

Spark by Hilton Guilford

Spark by Hilton Guilford

10/10 Excellent
"Clean room and building. Pleasant and efficient staff. Would stay there again."
Amber 1-night trip
Posted 4 days ago
Spark by Hilton Guilford

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 traveler 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.