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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 349
AED 936 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, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 349
AED 936 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 1,303 total
includes taxes & fees
2 Nov - 3 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 1,653 total
includes taxes & fees
3 Nov - 4 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 1,116 total
includes taxes & fees
27 Oct - 28 Oct
American Beech in Greenport - Petite King Room 7
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.

6. 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 843
AED 1,966 total
includes taxes & fees
11 Nov - 12 Nov
Renovated Townhouse walk to all
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 1,058
AED 2,245 total
includes taxes & fees
2 Nov - 3 Nov
Northfork Townhouse walk to all
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, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is AED 2,380
AED 4,113 total
includes taxes & fees
10 Nov - 11 Nov
Beachfront Greenport Villa
A dining area with a round table, six chairs, and a chandelier.

9. 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 323
AED 4,741 total
includes taxes & fees
8 Nov - 9 Nov
Year round Jacuzzi - Blackberry East Hampton Home
A dining area with a wooden table and white chairs, a teal bookshelf with decorative items, and a window with blinds.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (68 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 430
AED 1,023 total
includes taxes & fees
31 Oct - 1 Nov
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

11. 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 512
AED 2,058 total
includes taxes & fees
27 Oct - 28 Oct
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A hot tub with a checkered roof structure and surrounding greenery.

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 261
AED 5,698 total
includes taxes & fees
28 Oct - 29 Oct
Jacuzzi year-round - Villa Luz Private Home
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

13. 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 1,880
AED 4,132 total
includes taxes & fees
27 Oct - 28 Oct
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A greenhouse with a checkered floor, a table with a lamp, and a potted plant.

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 841
AED 1,246 total
includes taxes & fees
24 Nov - 25 Nov
American Beech in Greenport - Deluxe King 6
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 2,157 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.
Beachfront Jacuzzi All Year - Black Swan Home
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

17. 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)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AED 596
AED 1,707 total
includes taxes & fees
27 Oct - 28 Oct
Adorable Cottage, 5 min walk to water & town
A wooden interior with a staircase, a blue sofa, and a fireplace.

18. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Breakwater Estate: Heated Saltwater Pool, Sleeps 12
Mattituck
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is AED 3,813
AED 6,873 total
includes taxes & fees
25 Nov - 26 Nov
Breakwater Estate: Heated Saltwater Pool, Sleeps 12
A house with a covered outdoor seating area, a well-maintained lawn, and a sunset 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)
"Great home overall. Backyard was huge! Pool and seating options were was amazing!"
United States
Vanessa S.
The price is AED 1,873
AED 4,603 total
includes taxes & fees
31 Oct - 1 Nov
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.
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"A wonderful getaway. It was lovely. The room was beautiful with a fireplace they came and started for us. We had a balcony over looking the marina, and river. The sunrises were amazing. Great places to walk or take a resort bike. We were there in October and it was great. I will take out of season any day. Old Saybrook is a treasure."
Dana 2-night trip
Posted 3 hours ago
Saybrook Point Resort & Marina