Search Cottages in Southold

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 172 Cottages in Southold with updated reviews, rates, and availability.

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
The price is SAR 810
SAR 1,889 total
includes taxes & fees
17 Feb - 18 Feb
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (13)
"The cottage is cozy and clean. It has everything I need. and perfect for me and my dogs. We enjoyed our stay and had a nice winter break. We hope to come back next year. Thank you, Robin!"
The gardners Cottage 1 mile from long Island Sound - pet friendly

Hampton Cottage.

10.0 out of 10, Exceptional, (3)
"we had a great stay at this property. the house was perfect. great value for the price. it is new and modern and extremely clean. the area itself was also nice. on a dead end street so nice and secluded. the host also included many amenities for guests to use which was a plus. would definitely stay here again. "
The price is SAR 649
SAR 941 total
includes taxes & fees
25 Feb - 26 Feb
Hampton Cottage.

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (171)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country

Southold Cottage w/ Patio & Grill - Walk to Beach!

Southold Cottage w/ Patio & Grill - Walk to Beach!

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

9.8 out of 10, Exceptional, (26)
"Beautiful place, clean , enjoyable beachside"
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

Charming and Bright Cottage with Salt Water Pool

10.0 out of 10, Exceptional, (5)
"My husband and I stayed here for a weekend in September and loved every minute. Cottage was well decorated, very clean and had everything you would need. We loved the outdoor shower and the host was so accommodating and thoughtful. Highly recommend and hope to return soon. "
Charming and Bright Cottage with Salt Water Pool

Town walking distance-Bridgehampton Cottage

9.4 out of 10, Exceptional, (10)
"Great last minute stay with our pup. House offered ability to have our dog and a back yard for him to play."
Town walking distance-Bridgehampton Cottage

Beach access Cozy Cottage

9.8 out of 10, Exceptional, (6)
"Very clean and adorable place providing all one needs for peace and respite. I would return again."
Beach access Cozy Cottage

Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent Host, great stay, beautiful property and set up and very modern."
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!

70 Year old cottage on 2.8 acres, stunning views and sunsets

8.4 out of 10, Very Good, (6)
"We all liove the various Connecticut shore towns, and Ild Lyme was delightful. We revisited some favorite spots, and discovered a few new ones. The vintage appliances were particularly nice to find, and looking at old photos, we realized that the original cottage was really 100 years old!"
70 Year old cottage on 2.8 acres, stunning views and sunsets

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is SAR 353
SAR 653 total
includes taxes & fees
17 Feb - 18 Feb
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (33)
"Lovely little cottage in a pretty, quiet neighborhood. Once you find it down the little lane, it's a great location to be in. Not far from town and close to the water, we really enjoyed relaxing at the house and in the backyard. Highly recommend."
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (24)
"A five star review is not enough for this beautiful property! It is so well appointed, with everything you can possibly imagine to make your stay nothing less than perfect! It is an immaculate place that is decorated beautifully and the moment you open the door here you know you’ve chosen a charming and beautiful place to stay. The owner, Bill, was readily available prior to arriving to answer any questions we had. Even after we were here, he was in communication with us, which is always a...
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

East Hampton/Springs Cottage- minutes walk to sea

10.0 out of 10, Exceptional, (4)
"The home is very quaint and well appointed. There were many things that we could avail ourselves with. A kayak, a bike, beach chairs, greens in the garden, BBQ grill, a very nice pair of binoculars, a boogie board etc. Lots of interesting wall decorations of drawings and paintings. Close to the very nice towns of Montauk and Sag Harbor. The beach is nearby. For the ocean side we really enjoyed Hither Hills State Park."
East Hampton/Springs Cottage- minutes walk to sea

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"We had a magical Christmas here. I fulfilled a lifelong dream to host my family for Christmas Eve Smorgasbord and the jigsaw puzzle had all of the pieces! "
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
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.
Don't see what you're looking for?
See all available properties in Southold
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southold

North Fork 7 Bedroom Farmhouse Escape

3.0 star property
9.4 out of 10, Exceptional, (3)
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could walk to the beach, but be aware that it’s down the busy road as someone else mentioned. It wasn’t luxurious, but everything was clean and comfortable. I appreciated that towels and linens were provided...
North Fork 7 Bedroom Farmhouse Escape

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is SAR 494
SAR 645 total
includes taxes & fees
17 Feb - 18 Feb
Windward Shores Ocean Resort

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball
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.

Frequently asked questions

Why book your cottage in Southold with Expedia?
Expedia has some wonderful cottages in Southold, so get ready for a memorable stay on nature’s doorstep. If you have a budget, select how much you’d like to spend and the preferred star rating of your property. Or, make your way to the filters to search for cottages with free WiFi or a kitchen. We’ll help you find the perfect digs whatever your trip looks like.
How can I find cheap cottages in Southold?
With Expedia’s convenient filter tool, locating cheap cottages in Southold is a cinch. To view properties that are friendly on the wallet, tailor your search results by amenities, star rating and budget.