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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Southold vacation homes

A covered patio with outdoor furniture, a door, and a view of a residential area.

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 AED 314
AED 846 total
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

2. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 349
AED 890 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

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 great stay!! "
United States
Callie E.
The price is AED 479
AED 1,278 total
includes taxes & fees
4 Nov - 5 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

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 AED 716
AED 1,574 total
includes taxes & fees
4 Nov - 5 Nov
Beach Block Hideaway
A patio area with wicker chairs and a table, surrounded by gravel and plants.

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 AED 731
AED 1,066 total
includes taxes & fees
4 Nov - 5 Nov
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 AED 876
AED 2,008 total
includes taxes & fees
4 Nov - 5 Nov
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
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is AED 1,603
AED 3,099 total
includes taxes & fees
10 Nov - 11 Nov
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 AED 859
AED 1,985 total
includes taxes & fees
1 Dec - 2 Dec
Renovated Townhouse walk to all
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

9. 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
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

10. 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 AED 1,926
AED 3,984 total
includes taxes & fees
4 Nov - 5 Nov
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A dining area with a round table, six chairs, and a chandelier.

11. 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 AED 353
AED 4,828 total
includes taxes & fees
8 Nov - 9 Nov
Year round Jacuzzi - Blackberry East Hampton Home
A greenhouse with a checkered floor, a table with a lamp, and a potted plant.

12. 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 AED 841
AED 1,204 total
includes taxes & fees
4 Nov - 5 Nov
American Beech in Greenport - Deluxe King 6
A hot tub with a checkered roof structure and surrounding greenery.

13. 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 AED 265
AED 6,390 total
includes taxes & fees
4 Nov - 5 Nov
Jacuzzi year-round - Villa Luz Private Home
A wooden interior with a staircase, a blue sofa, and a fireplace.

14. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Mattituck
10.0 out of 10, Exceptional, (39 reviews)
"House has so much character, I rent 7-8 weeks per year and every home is different.This house is the most organized I have ever been in but also the most character.Every room brings you to different place, the furniture is beautiful. Home is spacious.Grounds are larger than most in the Hamptons. Pool is spectacular!"
United States
Frank T.
The price is AED 1,987
AED 4,604 total
includes taxes & fees
10 Nov - 11 Nov
Breakwater Estate: Heated Saltwater Pool, Sleeps 12
A modern living room with a wooden accent wall, a flat-screen TV, a fireplace, and a dining area with a chair and table.

15. 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 AED 1,047
AED 1,956 total
includes taxes & fees
8 Nov - 9 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A modern building with large windows overlooking a beach.

16. 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 AED 453
AED 4,710 total
includes taxes & fees
8 Nov - 9 Nov
Beachfront Jacuzzi All Year - Black Swan Home
A wooden house with a front porch, white railings, and a double door.

17. COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...

COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
Southampton
9.2 out of 10, Wonderful, (29 reviews)
"I loved the area and the home was beautiful and very spacious."
United States
Melissa
The price is AED 7,852
AED 10,190 total
includes taxes & fees
4 Nov - 5 Nov
COLONIAL COMPOUND WITH OVERSIZED LIVING ROOMS, GYM, AND ARCADE ROOM, CLOSE...
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a black table set for four.

18. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
Lovely & Spacious Sag Harbor escape with heated pool
A cozy living room with a sofa, a coffee table, and a dining area with chairs.

19. NEW private studio 1.1 miles to beach in East Lyme

NEW private studio 1.1 miles to beach in East Lyme
East Lyme
The price is AED 397
AED 500 total
includes taxes & fees
4 Nov - 5 Nov
NEW private studio 1.1 miles to beach in East Lyme
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

20. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is AED 1,653
AED 3,873 total
includes taxes & fees
4 Nov - 5 Nov
Minutes from the beach, brand new 4 bedroom
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
"Very well designed"
Alexander 2-night trip
Posted 1 hour ago
Sound View Greenport