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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Southold vacation homes

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

1. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥22,273
￥47,036 total
includes taxes & fees
Oct 7 - Oct 8
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.

2. 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, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥26,959
￥62,389 total
includes taxes & fees
Sep 15 - Sep 16
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A wooden pathway leading to a beach with scattered rocks and greenery.

3. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥29,954
￥61,424 total
includes taxes & fees
Sep 15 - Sep 16
Beach Block Hideaway
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

4. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥29,954
￥57,742 total
includes taxes & fees
Sep 28 - Sep 29
The SandPiper
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 ￥36,713
￥54,934 total
includes taxes & fees
Sep 16 - Sep 17
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, (14 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.
Renovated Townhouse walk to all
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

7. 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 ￥25,438
￥72,441 total
includes taxes & fees
Sep 15 - Sep 16
Adorable Cottage, 5 min walk to water & town
A modern building with large windows overlooking a beach.

8. Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.4 out of 10, Exceptional, (19 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 ￥33,487
￥200,532 total
includes taxes & fees
Sep 27 - Sep 28
Black Swan Beachfront Home with Jacuzzi year round
A modern dining area with a wooden table, white chairs, and a chandelier.

9. 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 ￥74,654
￥127,590 total
includes taxes & fees
Sep 15 - Sep 16
Northfork Townhouse walk to all
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

10. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥150,000
￥227,186 total
includes taxes & fees
Sep 17 - Sep 18
Beachfront Greenport Villa
A dining area with a round table, six chairs, and a chandelier.

11. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
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 ￥13,518
￥198,265 total
includes taxes & fees
Sep 15 - Sep 16
BlackBerry Private home with jacuzzi yearlong
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

12. 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 ￥43,779
￥90,208 total
includes taxes & fees
Sep 22 - Sep 23
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

13. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"
United States
Kathleen Andrews K.
The price is ￥110,599
￥204,458 total
includes taxes & fees
Sep 15 - Sep 16
Work and Play Special! Extended Stay Discount
A stone pier leading to a beach with houses in the background.

14. 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 ￥19,201
￥44,024 total
includes taxes & fees
Oct 7 - Oct 8
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

15. 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, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ￥47,619
￥90,323 total
includes taxes & fees
Sep 17 - Sep 18
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

16. 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 ￥87,097
￥171,114 total
includes taxes & fees
Sep 15 - Sep 16
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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 ￥30,246
￥89,200 total
includes taxes & fees
Sep 16 - Sep 17
Beachside Bliss w/ Game Room, Gym & Golf Green
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

18. 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 ￥45,929
￥67,041 total
includes taxes & fees
Sep 20 - Sep 21
American Beech in Greenport - Deluxe King 6
A spacious living room with a stone fireplace, wooden beams, a white sofa, and a cowhide rug.

19. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
Sag Harbor
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home !"
United States
Nadja B.
The price is ￥115,208
￥220,254 total
includes taxes & fees
Sep 15 - Sep 16
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

20. 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)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥17,204
￥257,843 total
includes taxes & fees
Sep 21 - Sep 22
Villa Luz Family Home w/ heated pool & jacuzzi
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

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"Our stay was filled with quietness set in a backdrop of beautiful blue skies enveloping the peconic bay. What a great place to come apart and forget about the stress of the week, relax and unwind. My husband and I were pleased with our stay. Everyone was ao friendly and helpful Mario was very attentive to our requests. Thenk you, Mario! A few suggestions: . Blinds at the living room sliding window in addition to the curtains to create more privacy . A microwave in the rooms since the stove/oven is not hooked up . Possibly changing your WIFI provider to ensure the TV works without buffering interruption Thank you so much. We recommend this hotel for anyone wanting to come apart and rest in serenity."
Nina 3-night trip
Posted 5 hours ago
The Shoals Suites and Slips

Find out more about Southold

Southold Vacation Homes information

Number of reviews
4,556
Accommodation
1236 Vacation Homes
Lowest Price
￥13,779
Highest Price
￥116,659