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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

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 AED 440
AED 1,635 total
includes taxes & fees
19 May - 20 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.
Insta-worthy Couples Retreat: Perfect for romantic getaway!
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 AED 735
AED 1,640 total
includes taxes & fees
19 May - 20 May
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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.
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 AED 686
AED 1,659 total
includes taxes & fees
20 May - 21 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
The price is AED 1,097
AED 2,154 total
includes taxes & fees
22 May - 23 May
#35 - Beautiful 3 BR Beach Haven
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 AED 768
AED 1,167 total
includes taxes & fees
21 May - 22 May
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 AED 1,107
AED 2,310 total
includes taxes & fees
19 May - 20 May
Northfork Townhouse walk to all
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.8 out of 10, Exceptional, (11 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 AED 1,322
AED 2,589 total
includes taxes & fees
20 May - 21 May
Renovated Townhouse walk to all
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 AED 1,572
AED 5,193 total
includes taxes & fees
25 May - 26 May
BlackBerry Private home with jacuzzi yearlong
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, (16 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 AED 1,186
AED 5,336 total
includes taxes & fees
26 May - 27 May
Black Swan Beachfront Home with Jacuzzi year round
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 AED 695
AED 2,078 total
includes taxes & fees
19 May - 20 May
Beachside Bliss w/ Game Room, Gym & Golf Green
Dining

Summer is filling up-Beach, Shopping and Golf

Summer is filling up-Beach, Shopping and Golf
Clinton
10.0 out of 10, Exceptional, (4 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
Summer is filling up-Beach, Shopping and Golf
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, (137 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 AED 1,102
AED 2,373 total
includes taxes & fees
19 May - 20 May
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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, (18 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is AED 1,837
AED 3,118 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 AED 2,859
AED 5,650 total
includes taxes & fees
19 May - 20 May
Minutes from the beach, brand new 4 bedroom
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, (208 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 AED 2,678
AED 4,431 total
includes taxes & fees
14 Jun - 15 Jun
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
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 AED 3,173
AED 6,076 total
includes taxes & fees
20 May - 21 May
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
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 AED 1,914
AED 3,433 total
includes taxes & fees
19 May - 20 May
Cozy beach hose minutes from Hamptons
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 AED 698
AED 1,831 total
includes taxes & fees
19 May - 20 May
Historic New England home ,Reunions Beach pass
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

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

10/10 Excellent
"The cottage was absolutely lovely. Very clean, comfortable and relaxing. It was a bit too cool for the pool, but we did enjoy sitting around a lovely fire at night with a glass of wine! The staff was very friendly and accommodating. We enjoyed ourselves immensely and will be going back!"
Lisa 2-night trip
Posted 7 hours ago
North Fork Cottages & RV Resort