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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (56 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 349
AED 906 total
includes taxes & fees
10 Nov - 11 Nov
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 AED 349
AED 906 total
includes taxes & fees
9 Nov - 10 Nov
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, (34 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 AED 533
AED 1,376 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 716
AED 1,649 total
includes taxes & fees
3 Nov - 4 Nov
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 AED 731
AED 1,125 total
includes taxes & fees
19 Oct - 20 Oct
American Beech in Greenport - Petite King Room 7
A two-story house with a well-maintained lawn and a stone fire pit in the foreground.

6. 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 228
AED 4,619 total
includes taxes & fees
18 Oct - 19 Oct
Year round Jacuzzi - Blackberry East Hampton Home
A modern dining area with a wooden table, white chairs, and a chandelier.

7. 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 942
AED 2,092 total
includes taxes & fees
2 Nov - 3 Nov
Northfork Townhouse walk to all
A modern building with large windows overlooking a beach.

8. 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 323
AED 4,283 total
includes taxes & fees
18 Oct - 19 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A bedroom with a bed, a chandelier, a door, and a wall-mounted decoration.

9. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is AED 1,140
AED 2,352 total
includes taxes & fees
12 Nov - 13 Nov
Renovated Townhouse walk to all
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

10. 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 AED 698
AED 2,304 total
includes taxes & fees
25 Oct - 26 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (64 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 AED 413
AED 993 total
includes taxes & fees
18 Oct - 19 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

12. 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 411
AED 6,128 total
includes taxes & fees
28 Oct - 29 Oct
Jacuzzi year-round - Villa Luz Private Home
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

13. 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 AED 2,231
AED 3,917 total
includes taxes & fees
4 Nov - 5 Nov
Beachfront Greenport Villa
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 AED 1,686
AED 2,371 total
includes taxes & fees
30 Oct - 31 Oct
American Beech in Greenport - Deluxe King 6
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

15. 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 1,978
AED 4,262 total
includes taxes & fees
17 Oct - 18 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

16. 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 AED 1,047
AED 2,157 total
includes taxes & fees
1 Nov - 2 Nov
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is AED 634
AED 2,020 total
includes taxes & fees
20 Oct - 21 Oct
Beachside Bliss w/ Game Room, Gym & Golf Green
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)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is AED 735
AED 1,644 total
includes taxes & fees
18 Oct - 19 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

19. 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 AED 2,123
AED 4,651 total
includes taxes & fees
20 Oct - 21 Oct
Amazing Southampton Home with Private Heated Pool
A rocky beach with clear water and a forested hillside in the background.

20. 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 AED 2,204
AED 5,036 total
includes taxes & fees
31 Oct - 1 Nov
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
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

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Inn is in a rural areas, along scenic country nestled in nature-immersed Riverhead town.Close to Riverheads amazing stores and popular eatery s They offer a more personal, relaxed atmosphere, often featuring a cozy bed rather than a corporate polish.. Great for a short business trip or as a overnite . Unique Inn atmosphere."
Elizabeth 2-night trip
Posted 7 hours ago
Greenview Inn Riverhead