Search Southold Cottage Rentals from CA $291

  • 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
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Southold cottages

Balcony

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is CA $255
CA $291 total
includes taxes & fees
May 12 - May 13
North Fork Cottages & RV Resort
Exterior

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is CA $159
CA $306 total
includes taxes & fees
May 14 - May 15
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is CA $308
CA $660 total
includes taxes & fees
May 14 - May 15
Beach Cottage, private beach and pass
Exterior

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (44 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is CA $524
CA $942 total
includes taxes & fees
May 20 - May 21
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Exterior

NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
The price is CA $395
CA $509 total
includes taxes & fees
May 14 - May 15
NEW Coastal Cottage 2 Miles to Beach + Lake Access
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
Greenport
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 CA $664
CA $1,224 total
includes taxes & fees
May 4 - May 5
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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 ; staff was friendly; Enough space for parking "
Marie 1-night trip
Posted 7 hours ago
Spark by Hilton Guilford

Find out more about Southold

Southold Cottages information

Number of reviews
96
Accommodation
210 Cottages
Lowest Price
CA $291
Highest Price
CA $1,224

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.

Explore a world of travel with Expedia