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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (54 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is ￥14,996
￥39,676 total
includes taxes & fees
Nov 4 - Nov 5
The SandPiper
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, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥22,888
￥60,597 total
includes taxes & fees
Nov 5 - Nov 6
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

3. 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 ￥22,888
￥50,498 total
includes taxes & fees
Oct 12 - Oct 13
Aqua Vista
An outdoor dining area with hanging lights, palm trees, and a bar.

4. 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 ￥31,412
￥48,334 total
includes taxes & fees
Oct 7 - Oct 8
American Beech in Greenport - Petite King Room 7
A wooden pathway leading to a beach with scattered rocks and greenery.

5. 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 ￥38,673
￥81,515 total
includes taxes & fees
Oct 12 - Oct 13
Beach Block Hideaway
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 ￥44,040
￥94,681 total
includes taxes & fees
Nov 2 - Nov 3
Northfork Townhouse walk to all
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.

7. 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 ￥46,899
￥97,604 total
includes taxes & fees
Oct 20 - Oct 21
Renovated 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 ￥99,483
￥173,195 total
includes taxes & fees
Oct 20 - Oct 21
Beachfront Greenport Villa
A dining area with a round table, six chairs, and a chandelier.

9. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry 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 ￥13,891
￥203,737 total
includes taxes & fees
Oct 7 - Oct 8
Year round Jacuzzi - Blackberry Home
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

10. 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 ￥36,148
￥54,465 total
includes taxes & fees
Oct 12 - Oct 13
American Beech in Greenport - Deluxe King 6
A modern building with large windows overlooking a beach.

11. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 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 ￥22,257
￥194,695 total
includes taxes & fees
Oct 12 - Oct 13
Beachfront Jacuzzi All Year - Black Swan Home
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 ￥44,987
￥92,697 total
includes taxes & fees
Nov 1 - Nov 2
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

13. 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 ￥29,992
￥98,287 total
includes taxes & fees
Oct 11 - Oct 12
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

14. 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 ￥89,501
￥175,837 total
includes taxes & fees
Oct 7 - Oct 8
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

15. 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 ￥17,679
￥253,239 total
includes taxes & fees
Oct 7 - Oct 8
Jacuzzi year-round - Villa Luz Private Home
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

16. 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 ￥26,140
￥74,441 total
includes taxes & fees
Oct 7 - Oct 8
Adorable Cottage, 5 min walk to water & town
A stone pier leading to a beach with houses in the background.

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (62 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 ￥17,758
￥42,971 total
includes taxes & fees
Oct 19 - Oct 20
Insta-worthy Couples Retreat: Perfect for romantic getaway!
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 ￥31,582
￥71,138 total
includes taxes & fees
Oct 8 - Oct 9
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A rectangular swimming pool with a pebble border and a fire feature in the center.

19. Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids

Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
East Hampton North
10.0 out of 10, Exceptional, (1 review)
The price is ￥37,846
￥150,887 total
includes taxes & fees
Oct 8 - Oct 9
Heated Pool UNTIL NOVEMBER, Outdoor Fireplace & Basement Arcade, Great for Kids
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.
The price is ￥107,812
￥216,126 total
includes taxes & fees
Oct 21 - Oct 22
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

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great hotel with friendly staff, clean and comfortable rooms, and excellent service — I really enjoyed my stay!"
Antrii 1-night trip
Posted 3 hours ago
The Harbor Front Inn

Find out more about Southold

Southold Vacation Homes information

Number of reviews
322
Accommodation
1236 Vacation Homes
Lowest Price
￥39,676
Highest Price
￥253,239