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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Southold vacation 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 ￥19,546
￥71,681 total
includes taxes & fees
Jun 4 - Jun 5
Rogers Lake House (87) · CT College+Beach+USCGA
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 ￥30,509
￥73,454 total
includes taxes & fees
Jun 8 - Jun 9
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Terrace/patio

Tennis & Sea Escape - Hydrangeas in the Hamptons

Tennis & Sea Escape - Hydrangeas in the Hamptons
Westhampton Beach
The price is ￥23,492
￥62,637 total
includes taxes & fees
Jun 16 - Jun 17
Tennis & Sea Escape - Hydrangeas in the Hamptons
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥26,488
￥64,451 total
includes taxes & fees
Jun 4 - Jun 5
Adorable Cottage, 5 min walk to water & town
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, (59 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is ￥25,912
￥54,087 total
includes taxes & fees
Jun 15 - Jun 16
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Outdoor dining

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays Townhouse - Pool, Beach Access
Hampton Bays
The price is ￥50,384
￥100,496 total
includes taxes & fees
Jun 4 - Jun 5
Hampton Bays Townhouse - Pool, Beach Access
Smart TV, fireplace, books, offices

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
9.8 out of 10, Exceptional, (10 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ￥79,975
￥134,438 total
includes taxes & fees
Jul 2 - Jul 3
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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, (138 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 ￥56,676
￥114,190 total
includes taxes & fees
Jun 16 - Jun 17
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 ￥34,389
￥84,813 total
includes taxes & fees
Jun 29 - Jun 30
Historic New England home ,Reunions Beach pass
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
Westhampton Beach
10.0 out of 10, Exceptional, (210 reviews)
"Great host, everything that we needed for our trip was available, ample room for the 9 of us."
United States
matthew p.
The price is ￥85,653
￥152,499 total
includes taxes & fees
Jun 8 - Jun 9
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
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 ￥51,664
￥204,962 total
includes taxes & fees
Jun 7 - Jun 8
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 ￥61,181
￥117,413 total
includes taxes & fees
Jun 4 - Jun 5
Northfork Townhouse walk to all
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
9.8 out of 10, Exceptional, (21 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is ￥79,975
￥135,780 total
includes taxes & fees
Jun 29 - Jun 30
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ￥33,430
￥50,988 total
includes taxes & fees
Jun 7 - Jun 8
American Beech in Greenport - Petite King Room 7
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 ￥80,432
￥156,556 total
includes taxes & fees
Jul 1 - Jul 2
Beachside Bliss w/ Game Room, Gym & Golf Green
Smart TV

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
East Lyme
9.8 out of 10, Exceptional, (23 reviews)
"I’ve stayed at this property for 3 summers in a row and every time it has been perfect. Lots of room, very clean and a perfect view!"
United States
Elisa N.
The price is ￥286,572
￥432,213 total
includes taxes & fees
Jun 20 - Jun 21
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 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 ￥57,582
￥112,755 total
includes taxes & fees
Jun 4 - Jun 5
Renovated Townhouse walk to all
Terrace/patio

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (17 reviews)
"The most amazing 24hrs! House is pristine, gorgeous view and very airy. Bedrooms each have their own bathroom and one more in the main living area. "
United States
Melissa M.
The price is ￥51,664
￥233,110 total
includes taxes & fees
Jun 7 - Jun 8
Black Swan Beachfront Home with Jacuzzi year round
Outdoor pool, a heated pool

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is ￥75,576
￥158,363 total
includes taxes & fees
Jun 7 - Jun 8
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is ￥238,517
￥311,357 total
includes taxes & fees
Jun 5 - Jun 6
Cozy 5 Bedroom With Wi-fi And Air Condition
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

Zey Hotel

Zey Hotel

10/10 Excellent
"This place was really unique well kept really close to everything since is in the middle of town and on main street really liked they had coffee, juice and a few pastries to get you started in the morning the staff was amazing!!! James( the manager) and jessica (housekeeping) know exactly what they are doing not to mention how nice and helpful they were we even added an extra night to our stay cause we didn't want to leave can not wait to go back!"
Carime 2-night trip
Posted 2 hours ago
Zey Hotel

Find out more about Southold

Southold Vacation Homes information

Number of reviews
622
Accommodation
1666 Vacation Homes
Lowest Price
￥50,988
Highest Price
￥432,213