Holiday Homes in Southold

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Our top choices for Southold holiday homes

10.0 out of 10, Exceptional, (5 reviews)
"Communication was excellent. "
United States
Katy C.
The price is €391
includes taxes & fees
3 Mar - 4 Mar
Rogers Lake House (87) · CT College+Beach+USCGA
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €172
includes taxes & fees
3 Mar - 4 Mar
American Beech in Greenport - Petite King Room 7
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is €711
includes taxes & fees
3 Mar - 4 Mar
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is €408
includes taxes & fees
10 Mar - 11 Mar
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
The price is €596
includes taxes & fees
15 Mar - 16 Mar
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is €304
includes taxes & fees
3 Mar - 4 Mar
Stylish Modern Stay Steps from the Ocean

Holiday Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is €545
includes taxes & fees
3 Mar - 4 Mar
Immaculate Waterfront 2 bedroom!

Holiday Home in Greenport

Northfork Townhouse walk to all
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is €454
includes taxes & fees
3 Mar - 4 Mar
Northfork Townhouse walk to all

Holiday Home in Greenport

Renovated Townhouse walk to all
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is €464
includes taxes & fees
3 Mar - 4 Mar
Renovated Townhouse walk to all
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
Beachside Bliss w/ Game Room, Gym & Golf Green

Holiday Home in Calverton

Cozy beach hose minutes from Hamptons
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is €598
includes taxes & fees
9 Mar - 10 Mar
Cozy beach hose minutes from Hamptons
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
The price is €931
includes taxes & fees
3 Mar - 4 Mar
Minutes from the beach, brand new 4 bedroom

Holiday Home in Greenport

Beachfront Greenport Villa
9.6 out of 10, Exceptional, (10 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
The price is €737
includes taxes & fees
3 Mar - 4 Mar
Beachfront Greenport Villa
The price is €491
includes taxes & fees
2 Apr - 3 Apr
Prime location, walk to all, cozy cottage Westhampton Beach
9.2 out of 10, Wonderful, (11 reviews)
"Great location. Great host. Easy house, pool and private back yard. It's modest but has it all."
United States
Harry V.
The price is €956
includes taxes & fees
13 Mar - 14 Mar
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
10.0 out of 10, Exceptional, (1 review)
The price is €712
includes taxes & fees
23 Mar - 24 Mar
Beach cottage, private road, private beach, private mooring, private parking.
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is €4,638
includes taxes & fees
3 Mar - 4 Mar
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
The price is €1,644
includes taxes & fees
3 Mar - 4 Mar
Cozy 5 Bedroom With Wi-fi And Air Condition
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is €1,315
includes taxes & fees
3 Mar - 4 Mar
Cozy Hamptons Escape 3BR Minutes From Beach!

Holiday Home in East Hampton

Gorgeous 5-Bedroom House in East Hampton
The price is €2,478
includes taxes & fees
9 Mar - 10 Mar
Gorgeous 5-Bedroom House in East Hampton
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

Find out more about Southold

Southold Holiday Homes information

Number of reviews
74
Accommodation
1732 Holiday Homes
Lowest Price
€172
Highest Price
€4,638