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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Cottages in Southold

Our top choices for Southold cottages

Pet-friendly Home w/ Hot Tub Near the Hamptons!
House (1 Bedroom) | Interior

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

3.0 star property
Pet-friendly Home w/ Hot Tub Near the Hamptons!
Hamptons Vacation Rental w/ Seasonal Pool!
Cottage (3 Bedrooms) | Interior

Hamptons Vacation Rental w/ Seasonal Pool!

3.0 star property
Hamptons Vacation Rental w/ Seasonal Pool!
Dreamy Waterfront Westbrook Home on Private Beach
House (3 Bedrooms) | Interior

Dreamy Waterfront Westbrook Home on Private Beach

3.0 star property
Dreamy Waterfront Westbrook Home on Private Beach
Charming Old Lyme Cottage, Steps to Private Beach!
Cottage (2 Bedrooms) | Interior

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!
Shelter Island Retreat w/ Outdoor Pool!
House (5 Bedrooms) | Interior

Shelter Island Retreat w/ Outdoor Pool!

3.0 star property
Shelter Island Retreat w/ Outdoor Pool!
Westbrook Home w/ Ocean Views - Walk to Beach
House (2 Bedrooms) | Interior

Westbrook Home w/ Ocean Views - Walk to Beach

3.0 star property
Westbrook Home w/ Ocean Views - Walk to Beach
Hamptons Bay Home on Shinnecock Bay w/ Yard!
House (2 Bedrooms) | Interior

Hamptons Bay Home on Shinnecock Bay w/ Yard!

3.0 star property
Hamptons Bay Home on Shinnecock Bay w/ Yard!
Cozy Westbrook Vacation Rental - Walk to Beach!
House (3 Bedrooms) | Interior

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!
Classy Getaway w/ Deck & Yard < 1 Mi to Beach
House (4 Bedrooms) | Interior

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

3.0 star property
Classy Getaway w/ Deck & Yard < 1 Mi to 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 Hampton Bays Home 5 Mi to Coopers Beach
House (3 Bedrooms) | Interior

Charming Hampton Bays Home 5 Mi to Coopers Beach

3.0 star property
Charming Hampton Bays Home 5 Mi to Coopers Beach
Hampton Bays Retreat: Walk to Squires Beach!
House (2 Bedrooms) | 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!
Unique Southampton Getaway w/ Rooftop Deck!
House (3 Bedrooms) | Interior

Unique Southampton Getaway w/ Rooftop Deck!

3.0 star property
Unique Southampton Getaway w/ Rooftop Deck!
Waterfront Cottage w/ Sunroom + Patio & Grill
Cottage (2 Bedrooms) | Interior

Waterfront Cottage w/ Sunroom + Patio & Grill

3.0 star property
Waterfront Cottage w/ Sunroom + Patio & Grill
Historic Essex Home w/ Large Yard Near Downtown!
House (2 Bedrooms) | Interior

Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing Host. Fantastic trip "
Historic Essex Home w/ Large Yard Near Downtown!
Mattituck Home w/ Fireplaces - Near Wineries
House (3 Bedrooms) | Interior

Mattituck Home w/ Fireplaces - Near Wineries

3.0 star property
Mattituck Home w/ Fireplaces - Near Wineries
Cute East Hampton Cottage w/ Patio - Walk to Beach
Cottage (2 Bedrooms) | Interior

Cute East Hampton Cottage w/ Patio - Walk to Beach

3.0 star property
Cute East Hampton Cottage w/ Patio - Walk to Beach
Charming Old Saybrook Home: Half-mi to Sand & Sea!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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

3.0 star property
Charming Old Saybrook Home: Half-mi to Sand & Sea!
Walk to Amagansett Beach: Cottage w/ Deck!
Cottage (4 Bedrooms) | Interior

Walk to Amagansett Beach: Cottage w/ Deck!

3.0 star property
Walk to Amagansett Beach: Cottage w/ Deck!
Villa Gavin
Fridge, microwave, stovetop, dishwasher

Villa Gavin

3.5 star property
Villa Gavin
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.
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Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"The staff was excellent. Very friendly and accommodating. And the room was comfortable and clean."
Brian 1-night trip
Posted 1 day ago
Pier Blue Inn Old Saybrook - Essex

Frequently asked questions

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