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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4
In one month
May 16 - May 18
In two months
Jun 13 - Jun 15

Compare 54 Cottages in Southold with updated reviews, rates, and availability.

Hamptons Bay Home on Shinnecock Bay w/ Yard!
House (2 Bedrooms) | Private kitchen | Paper towels

Hamptons Bay Home on Shinnecock Bay w/ Yard!

3.0 star property
Hamptons Bay Home on Shinnecock Bay w/ Yard!
Charming Old Lyme Cottage, Steps to Private Beach!
Cottage (2 Bedrooms) | Private kitchen

Charming Old Lyme Cottage, Steps to Private Beach!

2.0 star property
10.0 out of 10, Exceptional, (1)
Charming Old Lyme Cottage, Steps to Private Beach!
Cozy Westbrook Vacation Rental - Walk to Beach!
Property grounds

Cozy Westbrook Vacation Rental - Walk to Beach!

3.0 star property
4.0 out of 10, (1)
"The property was clean. The pictures in the ads made it clear that it was supposed to be a waterfront property. It was not. The pictures were taken on a neighbors private property that actually does sit on the water. The fireplace did not work. The only beach access was through a public park which was immediately next to the house. There were several slats missing from the blinds in the bedroom facing the parking lot which was about 8 feet away. Very disappointing for what was supposed to be a...
Cozy Westbrook Vacation Rental - Walk to Beach!
Hamptons Vacation Rental w/ Seasonal Pool!
Property grounds

Hamptons Vacation Rental w/ Seasonal Pool!

3.0 star property
Hamptons Vacation Rental w/ Seasonal Pool!
Villa Gavin
Balcony

Villa Gavin

3.5 star property
Villa Gavin
Shelter Island Retreat w/ Outdoor Pool!
Outdoor pool

Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
Historic Essex Home w/ Large Yard Near Downtown!
TV

Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
Historic Essex Home w/ Large Yard Near Downtown!
Westbrook Home w/ Ocean Views - Walk to Beach
Interior

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Waterfront Cottage w/ Sunroom + Patio & Grill
Living area

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Unique Southampton Getaway w/ Rooftop Deck!
Interior

Unique Southampton Getaway w/ Rooftop Deck!

3.0 star property
Unique Southampton Getaway w/ Rooftop Deck!
Hampton Bays Retreat: Walk to Squires Beach!
Interior

Hampton Bays Retreat: Walk to Squires Beach!

3.0 star property
6.0 out of 10, (1)
"Getting in and out of the property was very difficult. All the codes for the front door did not work and we were on the phone for an hour trying to get in. We had to go through the rental company as the owner didn’t answer any of our calls or texts. Also, locking the front door was very problematic. None of the shampoo, conditioner, or soap dispensers worked. The sheets were so itchy and horrible that we had to switch from the queen bed to the twin beds. Overall, the beds didn’t feel very clean...
Hampton Bays Retreat: Walk to Squires Beach!
Walk to Beach: Long Island Wine Country Home!
House (3 Bedrooms) | Interior

Walk to Beach: Long Island Wine Country Home!

3.0 star property
Walk to Beach: Long Island Wine Country Home!
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Exterior

Charming Old Saybrook Home: Half-mi to Sand & Sea!

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Mattituck Home w/ Fireplaces - Near Wineries
TV, fireplace

Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries
Pet-friendly Home w/ Hot Tub Near the Hamptons!
Interior

Pet-friendly Home w/ Hot Tub Near the Hamptons!

3.0 star property
Pet-friendly Home w/ Hot Tub Near the Hamptons!
Charming Hampton Bays Home 5 Mi to Coopers Beach
Terrace/patio

Charming Hampton Bays Home 5 Mi to Coopers Beach

3.0 star property
Charming Hampton Bays Home 5 Mi to Coopers Beach
Charming Westbrook Cottage, Steps to Private Beach
Interior

Charming Westbrook Cottage, Steps to Private Beach

3.0 star property
Charming Westbrook Cottage, Steps to Private Beach
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
Interior

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

3.0 star property
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!
Classy Getaway w/ Deck & Yard < 1 Mi to Beach
Terrace/patio

Classy Getaway w/ Deck & Yard < 1 Mi to Beach

3.0 star property
Classy Getaway w/ Deck & Yard < 1 Mi to Beach
Coastal Getaway w/ Porch, 2 Mi to Niantic Beach!
Fireplace

Coastal Getaway w/ Porch, 2 Mi to Niantic Beach!

3.0 star property
Coastal Getaway w/ Porch, 2 Mi to Niantic Beach!
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
Sign in
Sign up, it's free

Other property types in Southold

Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"2nd loft bedroom/bath was especially nice"
The price is NT$4,631
NT$5,997 total
includes taxes & fees
Apr 20 - Apr 21
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Condo | 2 bedrooms, iron/ironing board, free WiFi

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is NT$4,679
NT$6,758 total
includes taxes & fees
Apr 30 - May 1
Cliffside Resort Condominiums
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.