Southold Holiday House Rentals from AU$319: Search Holiday Homes

Southold Holiday Homes
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Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.

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Our top choices for Southold holiday homes

Holiday Home in Southold

Beautifully farmhouse

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"good experience"

Anonymous traveller

The price is AU$1,718

AU$1,718

includes taxes & fees

26 Jan - 27 Jan

Beautifully farmhouse

3 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"

Hemie J.

The price is AU$586

AU$586

includes taxes & fees

19 Jan - 20 Jan

Rogers Lake House (87) · CT College+Beach+USCGA

Holiday Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 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)."

Sarah G.

The price is AU$517

AU$517

includes taxes & fees

19 Jan - 20 Jan

The Bay Cottage · Rocky Neck Park, Beach & Niantic

Holiday Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Highly recommend everything from start to finish went smoothly and it was a great experience!!"

Stephanie M.

The price is AU$10,734

AU$10,734

includes taxes & fees

19 Jan - 20 Jan

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Holiday Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green

2.0 star property

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Perfect house for 6 guests. Loved that it was close to the beach."

Shannon G.

The price is AU$713

AU$713

includes taxes & fees

21 Jan - 22 Jan

Beachside Bliss w/ Game Room, Gym & Golf Green

Holiday Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

2.0 star property

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "

Elya D.

The price is AU$814

AU$814

includes taxes & fees

19 Jan - 20 Jan

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

4 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

9.6 out of 10, Exceptional, (22 reviews)

9.6/10

Exceptional

(22 reviews)

"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"

Annie B.

The price is AU$1,950

AU$1,950

includes taxes & fees

20 Jan - 21 Jan

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

4 bedrooms, travel cot, free WiFi, bed sheets

Holiday Home in East Hampton

Blackberry: Private home with jacuzzi year-round

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "

Suzanne R.

The price is AU$1,414

AU$1,414

includes taxes & fees

8 Feb - 9 Feb

Blackberry: Private home with jacuzzi year-round

Holiday Home in Clinton

Stylish Modern Stay Steps from the Ocean

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "

Kelly Z.

The price is AU$504

AU$504

includes taxes & fees

23 Jan - 24 Jan

Stylish Modern Stay Steps from the Ocean

Holiday Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"Nice house. Photos and descriptions represent it very accurately. "

Will K.

The price is AU$1,859

AU$1,859

includes taxes & fees

25 Jan - 26 Jan

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Holiday Home in Bay Point

Sag Harbor Water View w Dock 1.5ml from town

The price is AU$9,124

AU$9,124

includes taxes & fees

19 Jan - 20 Jan

Sag Harbor Water View w Dock 1.5ml from town

1 bedroom, iron/ironing board, Internet, bed sheets

Holiday Home in Greenport

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"We thoroughly enjoyed our stay!"

Parent From The Heart, Inc. E.

The price is AU$319

AU$319

includes taxes & fees

19 Jan - 20 Jan

American Beech in Greenport - Petite King Room 7

Holiday Home in Westbrook Center

Adorable Cottage, 5 min walk to water & town

9.4 out of 10, Exceptional, (15 reviews)

9.4/10

Exceptional

(15 reviews)

"Very nice small place to stay by the beach and close to great coffee shop. "

Donovan V.

The price is AU$637

AU$637

includes taxes & fees

19 Jan - 20 Jan

Adorable Cottage, 5 min walk to water & town

Holiday Home in Sag Harbor

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is AU$9,307

AU$9,307

includes taxes & fees

23 Jan - 24 Jan

Spacious 5-bedroom house with water views and 2 houses from the bay.

Holiday Home in Saybrook Manor

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

9.6 out of 10, Exceptional, (134 reviews)

9.6/10

Exceptional

(134 reviews)

"We loved our stay!"

Deana L.

The price is AU$767

AU$767

includes taxes & fees

21 Jan - 22 Jan

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

On the beach, sun-loungers, beach towels

Holiday Home in Laurel

Beach cottage, private road, private beach, private mooring, private parking.

2.5 star property

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

The price is AU$1,166

AU$1,166

includes taxes & fees

19 Jan - 20 Jan

Beach cottage, private road, private beach, private mooring, private parking.

5 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Calverton

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property

8.6 out of 10, Excellent, (8 reviews)

8.6/10

Excellent

(8 reviews)

"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."

Nicole A.

The price is AU$979

AU$979

includes taxes & fees

18 Jan - 19 Jan

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Holiday Home in Greenport

Northfork Townhouse walk to all

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 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"

Beth R.

The price is AU$872

AU$872

includes taxes & fees

20 Jan - 21 Jan

Northfork Townhouse walk to all

Holiday Home in Sag Harbor

Newly Renovated Sag Harbor Beach House with Pool

2.0 star property

The price is AU$1,368

AU$1,368

includes taxes & fees

25 Jan - 26 Jan

Newly Renovated Sag Harbor Beach House with Pool

3 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Greenport

Renovated Townhouse walk to all

9.6 out of 10, Exceptional, (9 reviews)

9.6/10

Exceptional

(9 reviews)

"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "

Laura B.

The price is AU$827

AU$827

includes taxes & fees

20 Jan - 21 Jan

Renovated Townhouse walk to all

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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