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

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Our top choices for Southold vacation homes

1. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (48 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is ¥31,118
¥59,986 total
includes taxes & fees
Sep 10 - Sep 11
The SandPiper

2. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (41 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is ¥30,855
¥60,925 total
includes taxes & fees
Sep 8 - Sep 9
Aqua Vista

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, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ¥38,766
¥80,627 total
includes taxes & fees
Sep 9 - Sep 10
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

4. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
The price is ¥46,678
¥86,777 total
includes taxes & fees
Sep 16 - Sep 17
Beach Block Hideaway

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 ¥48,893
¥71,047 total
includes taxes & fees
Sep 16 - Sep 17
American Beech in Greenport - Petite King Room 7

6. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 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 ¥57,449
¥112,495 total
includes taxes & fees
Sep 17 - Sep 18
Renovated Townhouse walk to all

7. 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 ¥92,636
¥158,346 total
includes taxes & fees
Sep 17 - Sep 18
Northfork Townhouse walk to all

8. 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 ¥128,325
¥226,516 total
includes taxes & fees
Sep 16 - Sep 17
Work and Play Special! Extended Stay Discount

9. 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 ¥46,599
¥94,998 total
includes taxes & fees
Sep 16 - Sep 17
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

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, (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 ¥19,948
¥46,215 total
includes taxes & fees
Sep 15 - Sep 16
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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 ¥56,805
¥81,351 total
includes taxes & fees
Sep 8 - Sep 9
American Beech in Greenport - Deluxe King 6

12. 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 ¥27,937
¥69,460 total
includes taxes & fees
Sep 15 - Sep 16
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ¥49,677
¥116,852 total
includes taxes & fees
Sep 15 - Sep 16
Beachside Bliss w/ Game Room, Gym & Golf Green

14. 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 ¥52,216
¥98,261 total
includes taxes & fees
Aug 31 - Sep 1
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

15. Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/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 ¥78,957
¥165,053 total
includes taxes & fees
Sep 14 - Sep 15
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

16. 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 ¥51,425
¥125,833 total
includes taxes & fees
Sep 9 - Sep 10
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

17. 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 ¥67,564
¥322,715 total
includes taxes & fees
Sep 8 - Sep 9
Villa Luz Family Home w/ heated pool & jacuzzi

18. 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 ¥198,705
¥274,692 total
includes taxes & fees
Aug 23 - Aug 24
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

19. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is ¥87,027
¥145,707 total
includes taxes & fees
Sep 1 - Sep 2
Immaculate Waterfront 2 bedroom!

20. NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here. The house has a cozy, homey feel and was a nice place to come back to after being out for the day. It was quiet, comfortable, and had a relaxed vibe that made the trip easy.The location was a big plus for us. Hammonasset Beach was only a few minutes away, and Madison center was just as close, which made it easy to grab dinner or pop out for anything we needed. The outdoor fireplace was also a really nice touch and made the evenings feel special.Overall, it was a...
United States
Moe B.
The price is ¥57,754
¥74,645 total
includes taxes & fees
Aug 23 - Aug 24
NEW Coastal Cottage 2 Miles to Beach + Lake Access
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

Find out more about Southold

Southold Vacation Homes information

Number of reviews
434
Accommodation
1591 Vacation Homes
Lowest Price
¥46,215
Highest Price
¥322,715