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

Southold Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Southold vacation rentals

Flat-screen TV

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is SAR 1,193
SAR 1,363 total
includes taxes & fees
16 Sep - 17 Sep
North Fork Resort
Condo | Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (284 reviews)
"Great place!"
United States
Christine
The price is SAR 1,151
SAR 1,649 total
includes taxes & fees
7 Sep - 8 Sep
Cliffside Resort Condominiums
Sun loungers, beach towels

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is SAR 732
SAR 1,411 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, (41 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is SAR 732
SAR 1,446 total
includes taxes & fees
8 Sep - 9 Sep
Aqua Vista
Beach

5. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (22 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is SAR 732
SAR 1,446 total
includes taxes & fees
13 Sep - 14 Sep
Harbor Heights
1 bedroom, desk, iron/ironing board, travel crib

6. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
The price is SAR 422
SAR 834 total
includes taxes & fees
15 Sep - 16 Sep
1-bedroom cottage with Grove Beach 🏖️ access.
Sun loungers, beach towels

7. 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, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is SAR 920
SAR 1,926 total
includes taxes & fees
7 Sep - 8 Sep
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Beach

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
The price is SAR 1,108
SAR 2,059 total
includes taxes & fees
8 Sep - 9 Sep
Beach Block Hideaway
Terrace/patio

9. 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 SAR 1,160
SAR 1,677 total
includes taxes & fees
7 Sep - 8 Sep
American Beech in Greenport - Petite King Room 7
Smart TV, offices

10. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is SAR 638
SAR 2,109 total
includes taxes & fees
19 Aug - 20 Aug
Seabreeze #3 Cozy Cottage steps to the beach
Property grounds

11. Safari Tent Glamping,S9-CedarPt, East Hampton, NY

Safari Tent Glamping,S9-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"It was relaxing and beautiful - a perfect and affordable getaway from the city! Also great proximity to so many fun things."
United States
Carolyn
The price is SAR 807
SAR 1,222 total
includes taxes & fees
23 Aug - 24 Aug
Safari Tent Glamping,S9-CedarPt, East Hampton, NY
1 bedroom, bed sheets

12. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is SAR 807
SAR 1,218 total
includes taxes & fees
20 Aug - 21 Aug
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Sun loungers, beach towels

13. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is SAR 591
SAR 1,374 total
includes taxes & fees
24 Aug - 25 Aug
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Dining

14. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is SAR 541
SAR 1,193 total
includes taxes & fees
18 Aug - 19 Aug
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Beach nearby

15. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is SAR 605
SAR 1,144 total
includes taxes & fees
18 Aug - 19 Aug
The Stern at Soundview · Beach+Ocean+Sunrise
Property grounds

16. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is SAR 3,565
SAR 5,613 total
includes taxes & fees
10 Sep - 11 Sep
Beachfront Greenport Villa
Beach nearby

17. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is SAR 629
SAR 1,443 total
includes taxes & fees
18 Aug - 19 Aug
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Terrace/patio

18. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
The price is SAR 726
SAR 1,113 total
includes taxes & fees
18 Aug - 19 Aug
Safari Tent Glamping,S7-CedarPt, East Hampton, NY
Property grounds

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 SAR 1,106
SAR 2,250 total
includes taxes & fees
13 Sep - 14 Sep
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Coffee/tea maker, fridge, microwave, oven

20. 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 SAR 3,143
SAR 5,456 total
includes taxes & fees
15 Sep - 16 Sep
Work and Play Special! Extended Stay Discount
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
"The Hampton Maid has beautiful rooms and landscape. The staff is always very friendly and helpful"
Elizabeth 2-night trip
Posted 4 hours ago
The Hampton Maid

Frequently asked questions

Can I find a vacation rental in Southold?

Yes, we offer vacation rentals in Southold close to Custer Institute and Observatory, or you can select a secluded option if you're looking for extra privacy while you relax. Southold is known for its wineries and beaches. Make sure you have time to check out the gardens and football games during your trip.

What are some of the best vacation home rentals that Southold has to offer?

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!: Visitors give good reviews to this Southold vacation home rental, which is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Southold?

With 118 Expedia vacation rentals, you're sure to find just the right place for your Southold stay.

What’s there to see and do in Southold?

McCabe's Beach and Horton Lane Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Sparkling Pointe and Mattebella Vineyards are other places worth a visit.

What’s a vacation rental in Southold like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Southold. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.