A calm lake with a forest in the background during sunset.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Southold vacation homes

A beach with people relaxing, a pier extending into the water, and a clear sky.

1. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥28,117
￥67,998 total
includes taxes & fees
Sep 8 - Sep 9
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

2. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is ￥28,117
￥55,553 total
includes taxes & fees
Sep 10 - Sep 11
The SandPiper
A wooden pathway leading to a beach with scattered rocks and greenery.

3. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥31,241
￥66,992 total
includes taxes & fees
Sep 7 - Sep 8
Beach Block Hideaway
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥31,241
￥61,503 total
includes taxes & fees
Sep 8 - Sep 9
Aqua Vista
An outdoor dining area with hanging lights, palm trees, and a bar.

5. 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)
"Great place! So nice."
United States
Paul F.
The price is ￥38,290
￥57,294 total
includes taxes & fees
Sep 7 - Sep 8
American Beech in Greenport - Petite King Room 7
A modern dining area with a wooden table, white chairs, and a chandelier.

6. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (7 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 ￥84,351
￥147,624 total
includes taxes & fees
Sep 8 - Sep 9
Northfork Townhouse walk to all
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

7. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"It was close to a very pretty beach, which was nice. The neighborhood is very quiet. The only downside was that the bedrooms were up stairs and the stairs were very steep. I didn’t notice that in the write up to the property it might have changed my rental of it. I would rate it very highly for anyone that doesn’t have trouble with stairs. The air conditioning was excellent, and the property is well appointed the owners were lovely and responsive."
United States
Sandra Hart
The price is ￥28,373
￥77,833 total
includes taxes & fees
Sep 9 - Sep 10
Adorable Cottage, 5 min walk to water & town
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

8. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥148,844
￥235,046 total
includes taxes & fees
Sep 10 - Sep 11
Beachfront Greenport Villa
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

9. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is ￥118,235
￥214,340 total
includes taxes & fees
Sep 15 - Sep 16
Work and Play Special! Extended Stay Discount
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

10. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (13 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
The price is ￥65,434
￥121,677 total
includes taxes & fees
Sep 17 - Sep 18
Renovated Townhouse walk to all
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

11. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
The price is ￥45,660
￥93,536 total
includes taxes & fees
Sep 20 - Sep 21
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A stone pier leading to a beach with houses in the background.

12. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is ￥21,308
￥48,031 total
includes taxes & fees
Sep 29 - Sep 30
Insta-worthy Couples Retreat: Perfect for romantic getaway!

13. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (7 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 ￥23,331
￥64,334 total
includes taxes & fees
Sep 29 - Sep 30
The Bay Cottage · Rocky Neck Park, Beach & Niantic
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

14. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is ￥47,777
￥69,739 total
includes taxes & fees
Sep 17 - Sep 18
American Beech in Greenport - Deluxe King 6
A dining area with a round table, six chairs, and a chandelier.

15. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, Wonderful, (7 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 ￥68,570
￥273,958 total
includes taxes & fees
Sep 8 - Sep 9
BlackBerry Private home with jacuzzi yearlong
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

16. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is ￥72,095
￥156,683 total
includes taxes & fees
Sep 8 - Sep 9
Elegant 5-Bedroom Hamptons Home with Private Pool
A glass-enclosed patio with a wooden table and wicker chairs, surrounded by glass doors and windows offering views of a wooded area.

17. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 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.
The price is ￥31,882
￥101,149 total
includes taxes & fees
Sep 9 - Sep 10
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

18. 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, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is ￥46,140
￥90,791 total
includes taxes & fees
Sep 21 - Sep 22
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A modern kitchen with a central island, stainless steel appliances, and a skylight.

19. Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (26 reviews)
"Everything was in order. When there were a couple of very minor glitches, the manager of the property was immediately responsive - and glitch gone, fast. This was one of the smoothest VRBO experiences we've had, and we've had many."
United States
Carola C.
The price is ￥51,588
￥308,268 total
includes taxes & fees
Sep 7 - Sep 8
Villa Luz Family Home w/ heated pool & jacuzzi
A sandy beach with footprints leading to the water, a wooden bench, and a pair of shoes on the ground.

20. Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is ￥65,526
￥146,801 total
includes taxes & fees
Sep 20 - Sep 21
Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants
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

Budget Host East End

Budget Host East End

10/10 Excellent
"Clean room, well maintained, friendly staff."
Olga 3-night trip
Posted less than an hour ago
Budget Host East End

Find out more about Southold

Southold Vacation Homes information

Number of reviews
500
Accommodation
1591 Vacation Homes
Lowest Price
￥48,031
Highest Price
￥308,268