Holiday Homes in Southold

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Check prices for these dates

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

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 NZ$736
includes taxes & fees
3 June - 4 June
Rogers Lake House (87) · CT College+Beach+USCGA
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 NZ$670
includes taxes & fees
3 June - 4 June
Adorable Cottage, 5 min walk to water & town
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 NZ$669
includes taxes & fees
3 June - 4 June
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 NZ$622
includes taxes & fees
15 June - 16 June
Tennis & Sea Escape - Hydrangeas in the Hamptons
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 NZ$558
includes taxes & fees
15 June - 16 June
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 NZ$1,038
includes taxes & fees
4 June - 5 June
Hampton Bays Townhouse - Pool, Beach Access
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 NZ$1,153
includes taxes & fees
9 June - 10 June
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 NZ$869
includes taxes & fees
21 June - 22 June
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 NZ$1,544
includes taxes & fees
4 June - 5 June
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 NZ$2,090
includes taxes & fees
9 June - 10 June
BlackBerry Private home with jacuzzi yearlong
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 NZ$1,388
includes taxes & fees
3 June - 4 June
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 NZ$528
includes taxes & fees
4 June - 5 June
American Beech in Greenport - Petite King Room 7
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 NZ$1,054
includes taxes & fees
3 June - 4 June
Northfork Townhouse walk to all
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 NZ$1,786
includes taxes & fees
1 July - 2 July
Beachside Bliss w/ Game Room, Gym & Golf Green
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 NZ$1,221
includes taxes & fees
4 June - 5 June
Renovated Townhouse walk to all
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 NZ$1,849
includes taxes & fees
4 June - 5 June
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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 NZ$2,379
includes taxes & fees
7 June - 8 June
Black Swan Beachfront Home with Jacuzzi year round
Smart TV, fireplace, ping pong, books

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock

NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Water Mill
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 NZ$6,777
includes taxes & fees
15 June - 16 June
NEW Luxury 7BR Southampton Estate – Salt Pool & Sauna, <10min US Open Shinnecock
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is NZ$3,184
includes taxes & fees
3 June - 4 June
Cozy 5 Bedroom With Wi-fi And Air Condition
Dining

“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”

“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”
Mattituck
9.2 out of 10, Wonderful, (5 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is NZ$2,238
includes taxes & fees
3 June - 4 June
“North Fork Winter Escape – Cozy Farmhouse by the Vineyards”
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Great"
priscilla 1-night trip
Posted 6 hours ago
Sound View Greenport

Find out more about Southold

Southold Holiday Homes information

Number of reviews
595
Accommodation
1666 Holiday Homes
Lowest Price
NZ$528
Highest Price
NZ$6,777