Southold Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Southold vacation rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
$269 nightly
The price is $307
Nov 30 - Dec 1
Total with taxes and fees
Cliffside Resort Condominiums
A two-story house with a white staircase, a covered patio with outdoor furniture, and a fenced yard.

2. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$202 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
Harbor Heights
A covered patio with outdoor furniture, a door, and a view of a residential area.

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
$202 nightly
The price is $230
Nov 10 - Nov 11
Total with taxes and fees
The SandPiper
A modern house with a deck, outdoor seating, and a fire pit.

4. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
$296 nightly
The price is $338
Nov 8 - Nov 9
Total with taxes and fees
North Fork Resort
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

5. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
$212 nightly
The price is $242
Nov 9 - Nov 10
Total with taxes and fees
Aqua Vista
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

6. 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, (35 reviews)
"We had a great stay!! "
United States
Callie E.
$305 nightly
The price is $348
Nov 5 - Nov 6
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

7. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
$375 nightly
The price is $428
Nov 11 - Nov 12
Total with taxes and fees
Beach Block Hideaway
A patio area with wicker chairs and a table, surrounded by gravel and plants.

8. 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.
$254 nightly
The price is $290
Nov 5 - Nov 6
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Room

9. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (332 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
$156 nightly
The price is $178
Nov 18 - Nov 19
Total with taxes and fees
Windward Shores Ocean Resort
A single-story house with a gabled roof, a front porch, and a well-maintained garden.

10. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.8 out of 10, Excellent, (9 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$453 nightly
The price is $481
Nov 30 - Dec 1
Total with taxes and fees
Walk to Beach | Seabreeze Cottage #4
A modern dining area with a wooden table, white chairs, and a chandelier.

11. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 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.
$479 nightly
The price is $547
Nov 10 - Nov 11
Total with taxes and fees
Northfork Townhouse walk to all
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

12. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
$414 nightly
The price is $473
Nov 9 - Nov 10
Total with taxes and fees
Charming Accommodations in the Hamptons
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

13. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
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.

14. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
$479 nightly
The price is $547
Nov 10 - Nov 11
Total with taxes and fees
Renovated Townhouse walk to all
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

15. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
$780 nightly
The price is $891
Nov 11 - Nov 12
Total with taxes and fees
Beachfront Greenport Villa
A dining area with a round table, six chairs, and a chandelier.

16. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
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.
$1,251 nightly
The price is $1,314
Nov 8 - Nov 9
Total with taxes and fees
Year round Jacuzzi - Blackberry East Hampton Home
A modern loft apartment with a dining area, kitchenette, and a cozy seating area.

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.
$264 nightly
The price is $300
Nov 5 - Nov 6
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A hot tub with a checkered roof structure and surrounding greenery.

18. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,645 nightly
The price is $1,733
Nov 5 - Nov 6
Total with taxes and fees
Jacuzzi year-round - Villa Luz Private Home
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

19. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
$198 nightly
The price is $227
Nov 10 - Nov 11
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
A spacious living area with a white sofa, a white armchair, and a dining table. There is a staircase leading to an upper level.

20. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
$453 nightly
The price is $481
Nov 30 - Dec 1
Total with taxes and fees
Steps to the beach | Seabreeze Cottage #3
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

A beachside outdoor seating area with white Adirondack chairs and a fire pit.
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport

10/10 Excellent

We had a lovely stay.
United States
Nicole
Reviewed June 22, 2024
Silver Sands Motel & Beach Bungalows

Find out more about Southold

Everything you need to know about Southold vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southold vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southold vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southold vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southold. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southold in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $177 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southold rentals

At Expedia, we put the best Southold vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southold rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southold vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southold. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: You might want to consider this vacation rental near Southold, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 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 Croteaux 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.

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