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

Holiday Homes in Southold

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Southold holiday homes

Beach

1. 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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is €360
includes taxes & fees
8 Sept - 9 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Beach

2. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is €316
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
Beach

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 €354
includes taxes & fees
7 Sept - 8 Sept
Beach Block Hideaway
Beach

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (44 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is €330
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
Terrace/patio

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 €315
includes taxes & fees
7 Sept - 8 Sept
American Beech in Greenport - Petite King Room 7
Dining

6. 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 €766
includes taxes & fees
17 Sept - 18 Sept
Northfork Townhouse walk to all
Interior

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)
"It was close to a very pretty beach, which was nice. The neighborhood is very quiet. The only downside was that the bedrooms were up stairs and the stairs were very steep. I didn’t notice that in the write up to the property it might have changed my rental of it. I would rate it very highly for anyone that doesn’t have trouble with stairs. The air conditioning was excellent, and the property is well appointed the owners were lovely and responsive."
United States
Sandra Hart
Adorable Cottage, 5 min walk to water & town
Property grounds

8. 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 €1,261
includes taxes & fees
10 Sept - 11 Sept
Beachfront Greenport Villa
Private kitchen

9. 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 €1,158
includes taxes & fees
15 Sept - 16 Sept
Work and Play Special! Extended Stay Discount
Living area

10. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (13 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
Property grounds

11. 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 €506
includes taxes & fees
20 Sept - 21 Sept
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Beach

12. 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 €254
includes taxes & fees
15 Sept - 16 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Beach

13. 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 €334
includes taxes & fees
29 Sept - 30 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Property grounds

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 €378
includes taxes & fees
15 Sept - 16 Sept
American Beech in Greenport - Deluxe King 6
Dining

15. 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 €1,482
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong
Pool

16. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is €840
includes taxes & fees
8 Sept - 9 Sept
Elegant 5-Bedroom Hamptons Home with Private Pool
Dining

17. 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.
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Interior

18. 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 €479
includes taxes & fees
21 Sept - 22 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Pool

19. 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 €1,664
includes taxes & fees
7 Sept - 8 Sept
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 Hampton Maid

The Hampton Maid

10/10 Excellent
"wonderful hotel."
SABINA 1-night trip
Posted 1 hour ago
The Hampton Maid

Find out more about Southold

Southold Holiday Homes information

Number of reviews
5,748
Accommodation
1252 Holiday Homes
Lowest Price
€78
Highest Price
€577