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

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
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 vacation homes

Beach

1. 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 AED 716
AED 1,532 total
includes taxes & fees
7 Sep - 8 Sep
Beach Block Hideaway
Sun loungers, beach towels

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, (30 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AED 645
AED 1,542 total
includes taxes & fees
8 Sep - 9 Sep
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Sun loungers, beach towels

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (51 reviews)
"access"
United States
Timothy
The price is AED 645
AED 1,274 total
includes taxes & fees
10 Sep - 11 Sep
The SandPiper
Sun loungers, beach towels

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 AED 716
AED 1,410 total
includes taxes & fees
20 Sep - 21 Sep
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 AED 1,098
AED 1,603 total
includes taxes & fees
2 Sep - 3 Sep
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 AED 2,000
AED 3,439 total
includes taxes & fees
17 Sep - 18 Sep
Northfork Townhouse walk to all
Smart TV, fireplace

7. 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.
The price is AED 1,504
AED 2,797 total
includes taxes & fees
17 Sep - 18 Sep
Renovated Townhouse walk to all
Coffee/tea maker, fridge, microwave, oven

8. 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 AED 2,938
AED 5,208 total
includes taxes & fees
30 Sep - 1 Oct
Work and Play Special! Extended Stay Discount
Property grounds

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 AED 1,047
AED 2,144 total
includes taxes & fees
20 Sep - 21 Sep
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Beach nearby

10. 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 AED 489
AED 1,101 total
includes taxes & fees
29 Sep - 30 Sep
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Dining

11. 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 AED 731
AED 2,323 total
includes taxes & fees
9 Sep - 10 Sep
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Property grounds

12. 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 AED 1,208
AED 1,746 total
includes taxes & fees
14 Sep - 15 Sep
American Beech in Greenport - Deluxe King 6
Beach nearby

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 AED 525
AED 1,460 total
includes taxes & fees
29 Sep - 30 Sep
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Outdoor pool, a heated pool

14. 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 AED 1,653
AED 3,592 total
includes taxes & fees
8 Sep - 9 Sep
Elegant 5-Bedroom Hamptons Home with Private Pool
Outdoor pool, a heated pool

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 AED 3,081
AED 5,367 total
includes taxes & fees
2 Sep - 3 Sep
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Beach

16. 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 AED 1,018
AED 2,523 total
includes taxes & fees
2 Sep - 3 Sep
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior

17. 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 AED 1,058
AED 2,081 total
includes taxes & fees
21 Sep - 22 Sep
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Property grounds

18. 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 AED 1,183
AED 7,067 total
includes taxes & fees
7 Sep - 8 Sep
Villa Luz Family Home w/ heated pool & jacuzzi
Smart TV, fireplace, DVD player, books

19. Beautiful East Hampton Retreat

Beautiful East Hampton Retreat
East Hampton
9.6 out of 10, Exceptional, (5 reviews)
"The host was very easy to work with. He was attentive and responsive. The home was exactly as advertised and was clean and nice to stay in!"
United States
Jonathan S.
The price is AED 2,727
AED 5,092 total
includes taxes & fees
2 Sep - 3 Sep
Beautiful East Hampton Retreat
Beach nearby, sun loungers, beach towels

20. Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
The price is AED 1,502
AED 3,366 total
includes taxes & fees
20 Sep - 21 Sep
Heart of Hamptons Retreat/Southampton/Beaches/5 Star Restaurants
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Reasonable price, nice staff, clean rooms. Fills the need for a short stay!"
Julia 1-night trip
Posted 1 hour ago
Pier Blue Inn Old Saybrook - Essex