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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Southold holiday 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, (46 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is £240
includes taxes & fees
7 Oct - 8 Oct
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 £323
includes taxes & fees
4 Oct - 5 Oct
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 £352
includes taxes & fees
15 Oct - 16 Oct
Beach Block Hideaway
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 £234
includes taxes & fees
7 Oct - 8 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.

5. 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.
The price is £484
includes taxes & fees
6 Oct - 7 Oct
Renovated Townhouse walk to all
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

6. 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 £909
includes taxes & fees
20 Oct - 21 Oct
Beachfront Greenport Villa
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 £339
includes taxes & fees
27 Sept - 28 Sept
Adorable Cottage, 5 min walk to water & town
A single-story house with a front porch, a driveway, and a well-maintained lawn.

8. Charming 2-bedroom cottage with AC in Westbrook

Charming 2-bedroom cottage with AC in Westbrook
Westbrook
The price is £173
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom cottage with AC in Westbrook
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

9. 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 £1,254
includes taxes & fees
29 Sept - 30 Sept
Jacuzzi year-round - Villa Luz Private Home
A modern dining area with a wooden table, white chairs, and a chandelier.

10. 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 £551
includes taxes & fees
20 Oct - 21 Oct
Northfork Townhouse walk to all
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 £916
includes taxes & fees
28 Sept - 29 Sept
Beachfront Jacuzzi All Year - Black Swan Home
A bedroom with a bed, bench, and windows with shutters.

12. Huge Island Getaway Pool Hot Tub Walk To Beach

Huge Island Getaway Pool Hot Tub Walk To Beach
Menantic Creek
9.8 out of 10, Exceptional, (9 reviews)
"Property great. Beautiful home with great amenities"
United States
Harry K.
The price is £916
includes taxes & fees
5 Oct - 6 Oct
Huge Island Getaway Pool Hot Tub Walk To Beach
A dining area with a round table, six chairs, and a chandelier.

13. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
The price is £980
includes taxes & fees
27 Sept - 28 Sept
Year round Jacuzzi - Blackberry Home
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

14. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (59 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 £974
includes taxes & fees
27 Sept - 28 Sept
Work and Play Special! Extended Stay Discount
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 £836
includes taxes & fees
25 Sept - 26 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A stone pier leading to a beach with houses in the background.

16. 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 £206
includes taxes & fees
29 Sept - 30 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

17. 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 £344
includes taxes & fees
27 Sept - 28 Sept
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

18. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (3 reviews)
"This house is absolutely wonderful and in a great location. It is beautifully decorated and the grounds are immaculate. The host has paid close attention to detail; everything we could ever need was there! We loved our stay, highly highly recommend ....."
United States
Carolyn C.
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

19. 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 £462
includes taxes & fees
1 Oct - 2 Oct
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

20. 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 £253
includes taxes & fees
1 Oct - 2 Oct
American Beech in Greenport - Deluxe King 6
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

Zey Hotel

Zey Hotel

10/10 Excellent
"Lovely hotel, great location and lovely courtyard!"
Martina 1-night trip
Posted 9 hours ago
Zey Hotel

Find out more about Southold

Southold Holiday Homes information

Number of reviews
346
Accommodation
1294 Holiday Homes
Lowest Price
£206
Highest Price
£1,254