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

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Southold vacation homes

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

1. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is ￥15,012
￥38,998 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

2. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥15,012
￥40,262 total
includes taxes & fees
Nov 9 - Nov 10
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.

3. 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, (35 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is ￥20,622
￥56,056 total
includes taxes & fees
Nov 2 - Nov 3
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden pathway leading to a beach with scattered rocks and greenery.

4. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥30,814
￥71,131 total
includes taxes & fees
Nov 3 - Nov 4
Beach Block Hideaway
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 ￥31,446
￥48,024 total
includes taxes & fees
Oct 20 - Oct 21
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
9.4 out of 10, Exceptional, (8 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 ￥39,110
￥88,193 total
includes taxes & fees
Nov 3 - Nov 4
Northfork Townhouse walk to all
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

7. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥87,464
￥155,713 total
includes taxes & fees
Nov 10 - Nov 11
Beachfront Greenport Villa
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.

8. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is ￥45,510
￥96,590 total
includes taxes & fees
Nov 3 - Nov 4
Renovated Townhouse walk to all
A modern building with large windows overlooking a beach.

9. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is ￥17,856
￥188,058 total
includes taxes & fees
Oct 27 - Oct 28
Beachfront Jacuzzi All Year - Black Swan Home
A dining area with a round table, six chairs, and a chandelier.

10. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
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 ￥9,797
￥198,721 total
includes taxes & fees
Oct 20 - Oct 21
Year round Jacuzzi - Blackberry East Hampton Home
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

11. 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 ￥36,187
￥54,345 total
includes taxes & fees
Oct 20 - Oct 21
American Beech in Greenport - Deluxe King 6
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

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

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is ￥85,117
￥183,366 total
includes taxes & fees
Oct 20 - Oct 21
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

13. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is ￥30,024
￥98,393 total
includes taxes & fees
Oct 25 - Oct 26
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

14. 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, (2 reviews)
"The property was great for our Hamptons trip! Very clean and comfortable and communication was great"
United States
Katie B.
The price is ￥45,036
￥92,798 total
includes taxes & fees
Nov 8 - Nov 9
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

15. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥17,698
￥263,259 total
includes taxes & fees
Oct 28 - Oct 29
Jacuzzi year-round - Villa Luz Private Home
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

16. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (3 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥20,163
￥77,270 total
includes taxes & fees
Oct 20 - Oct 21
Beachside Bliss w/ Game Room, Gym & Golf Green
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (65 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 ￥17,777
￥43,018 total
includes taxes & fees
Oct 28 - Oct 29
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

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

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (15 reviews)
"Cute little house with excellent amenities. Perfect for our cousins getaway!"
United States
Karol T.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A rocky beach with clear water and a forested hillside in the background.

19. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, Apple Picking & Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is ￥80,590
￥198,049 total
includes taxes & fees
Oct 24 - Oct 25
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

20. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is ￥76,621
￥180,769 total
includes taxes & fees
Oct 20 - Oct 21
Amazing Southampton Home with Private Heated Pool
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

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"This hotel was so conveniently located on a main road, right off the 495, near so many restaurants and stores and a few minute drive to the wineries and farms. The property was spotless and very nice and accommodating. We had a 2 queen room for a family of 4 and it was perfectly spacious. We have small kids so we used the pool and hot tub. The pool was a little too cold for my liking but my kids had a blast. The hotel was great all around. I am sure we will be back again next fall!"
Jenna 1-night trip
Posted less than an hour ago
Hilton Garden Inn Riverhead

Find out more about Southold

Southold Vacation Homes information

Number of reviews
303
Accommodation
1236 Vacation Homes
Lowest Price
￥38,998
Highest Price
￥263,259