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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Southold holiday homes

Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is HK$1,252
HK$3,892 total
includes taxes & fees
12 May - 13 May
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (56 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is HK$881
HK$2,124 total
includes taxes & fees
10 May - 11 May
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,638
HK$2,498 total
includes taxes & fees
10 May - 11 May
American Beech in Greenport - Petite King Room 7
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.2 out of 10, Wonderful, (5 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is HK$1,333
HK$3,389 total
includes taxes & fees
12 May - 13 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is HK$1,512
HK$8,760 total
includes taxes & fees
10 May - 11 May
BlackBerry Private home with jacuzzi yearlong
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
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 HK$2,503
HK$5,098 total
includes taxes & fees
11 May - 12 May
Northfork Townhouse walk to all
Exterior detail

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
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 HK$3,519
HK$6,571 total
includes taxes & fees
9 May - 10 May
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
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.
The price is HK$1,646
HK$4,661 total
includes taxes & fees
11 May - 12 May
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton
10.0 out of 10, Exceptional, (17 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is HK$3,918
HK$6,651 total
includes taxes & fees
1 Jun - 2 Jun
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is HK$3,526
HK$8,692 total
includes taxes & fees
12 May - 13 May
Minutes from the beach, brand new 4 bedroom
Interior

Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
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 HK$3,533
HK$6,605 total
includes taxes & fees
11 May - 12 May
Cozy beach hose minutes from Hamptons
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is HK$3,016
HK$5,874 total
includes taxes & fees
27 May - 28 May
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Terrace/patio

Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass
Guilford
9.2 out of 10, Wonderful, (90 reviews)
"This is a great location, walking distance to the green and other sites. It also worked well for our girls trip of 4 women."
United States
Liz H.
The price is HK$1,802
HK$4,305 total
includes taxes & fees
7 Jun - 8 Jun
Historic New England home ,Reunions Beach pass
TV, fireplace, stereo, offices

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is HK$6,769
HK$12,961 total
includes taxes & fees
20 May - 21 May
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
Interior

Stunning Bayfront Views

Stunning Bayfront Views
Hampton Bays
9.8 out of 10, Exceptional, (41 reviews)
"We really enjoyed our stay. House was clean, comfortable and in a beautiful location. Even an impendimg noreaster couldn't dampen our stay!"
United States
Maria G.
The price is HK$3,519
HK$9,704 total
includes taxes & fees
9 May - 10 May
Stunning Bayfront Views
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is HK$11,705
HK$15,137 total
includes taxes & fees
9 May - 10 May
Cozy 5 Bedroom With Wi-fi And Air Condition
Interior

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
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 HK$7,835
HK$10,223 total
includes taxes & fees
9 May - 10 May
Cozy Hamptons Escape 3BR Minutes From Beach!
Smart TV, fireplace

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is HK$31,340
HK$50,549 total
includes taxes & fees
11 May - 12 May
Spacious 5-bedroom house with water views and 2 houses from the bay.
Living area

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
The price is HK$3,526
HK$8,692 total
includes taxes & fees
15 May - 16 May
Minutes from the beach, brand new 3 bedroom
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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"The staff were great and the rooms were in greay shape and very comfortable. The location is close to many restaurants. "
DOMINICK 2-night trip
Posted 6 hours ago
The Bentley Hotel Southampton

Find out more about Southold

Southold Vacation Homes information

Number of reviews
379
Accommodation
1666 Vacation Homes
Lowest Price
HK$2,125
Highest Price
HK$50,549

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