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

A beach with people relaxing, a pier extending into the water, and a clear sky.

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 NZ$710
includes taxes & fees
8 Sept - 9 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

2. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is NZ$590
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
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 NZ$699
includes taxes & fees
14 Sept - 15 Sept
Beach Block Hideaway
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

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 NZ$632
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
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 NZ$730
includes taxes & fees
2 Sept - 3 Sept
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
9.4 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
A modern dining area with a wooden table, white chairs, and a chandelier.

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.
Northfork Townhouse walk to all
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

8. 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
The price is NZ$722
includes taxes & fees
9 Sept - 10 Sept
Adorable Cottage, 5 min walk to water & town
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

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 NZ$950
includes taxes & fees
29 Sept - 30 Sept
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.

10. 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 NZ$2,202
includes taxes & fees
10 Sept - 11 Sept
Work and Play Special! Extended Stay Discount
A stone pier leading to a beach with houses in the background.

11. 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 NZ$493
includes taxes & fees
30 Sept - 1 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

12. 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 NZ$2,372
includes taxes & fees
2 Sept - 3 Sept
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

13. 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 NZ$856
includes taxes & fees
22 Sept - 23 Sept
American Beech in Greenport - Deluxe King 6

14. 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 NZ$693
includes taxes & fees
28 Sept - 29 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

15. 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 NZ$1,255
includes taxes & fees
14 Sept - 15 Sept
Beachside Bliss w/ Game Room, Gym & Golf Green
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

16. 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 NZ$939
includes taxes & fees
28 Sept - 29 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A dining area with a round table, six chairs, and a chandelier.

17. 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 NZ$2,767
includes taxes & fees
8 Sept - 9 Sept
BlackBerry Private home with jacuzzi yearlong
A glass-enclosed patio with a wooden table and wicker chairs, surrounded by glass doors and windows offering views of a wooded area.

18. 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 NZ$1,028
includes taxes & fees
29 Sept - 30 Sept
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

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 NZ$3,127
includes taxes & fees
10 Sept - 11 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

Zey Hotel

Zey Hotel

10/10 Excellent
"The staff was very helpful and courteous."
RYAN 1-night trip
Posted 1 hour ago
Zey Hotel

Find out more about Southold

Southold Holiday Homes information

Number of reviews
446
Accommodation
1278 Holiday Homes
Lowest Price
NZ$493
Highest Price
NZ$3,127