Southold Vacation Rentals from $194: Search Short-Term Rentals

A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

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Our top choices for Southold vacation rentals

A kitchen with a wooden countertop, a black sink, and a window with a view of trees.

1. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

Southold

Kelly V.

$414 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

2. Cliffside Resort Condominiums

Greenport

William

$289 nightly

Nov 26 - Nov 27

Total with taxes and fees

A modern house with a deck, outdoor seating, and a fire pit.

3. North Fork Resort

Greenport

Altynai

$311 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with people relaxing on chairs and sunbathing.

4. Harbor Heights

Pipes Cove

Steven R.

$196 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

5. The SandPiper

Pipes Cove

Manuela C.

$205 nightly

Nov 30 - Dec 1

Total with taxes and fees

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

6. Aqua Vista

Pipes Cove

Carey D.

$212 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

7. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

$305 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden pathway leading to a beach with scattered rocks and greenery.

8. Beach Block Hideaway

Pipes Cove

Teresa C.

$375 nightly

Nov 15 - Nov 16

Total with taxes and fees

An outdoor dining area with hanging lights, palm trees, and a bar.

9. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

$254 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with footprints leading to the water, a sunset in the background, and a clear sky.

10. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"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...

Lydia

$429 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern dining area with a wooden table, white chairs, and a chandelier.

11. Northfork Townhouse walk to all

Greenport

Beth R.

$493 nightly

Dec 1 - Dec 2

Total with taxes and fees

A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

12. Cozy Cottage by the beach - Seabreeze #1

Hampton Bays

$423 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

13. Renovated Townhouse walk to all

Greenport

Liz H.

$463 nightly

Nov 18 - Nov 19

Total with taxes and fees

A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.

14. Beachfront Greenport Villa

Greenport

Kate R.

$793 nightly

Dec 1 - Dec 2

Total with taxes and fees

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

15. Charming Accommodations in the Hamptons

Sag Harbor

$434 nightly

Nov 16 - Nov 17

Total with taxes and fees

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

16. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

Marcy C.

$222 nightly

Nov 19 - Nov 20

Total with taxes and fees

A modern building with large windows overlooking a beach.

17. Beachfront Jacuzzi All Year - Black Swan Home

Hampton Bays

John M.

$1,214 nightly

Nov 15 - Nov 16

Total with taxes and fees

18. Windward Shores Ocean Resort

Napeague

Banessa

$170 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern living room with a sofa, coffee table, and dining area.

19. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

$712 nightly

Dec 1 - Dec 2

Total with taxes and fees

A residential property with a covered patio, outdoor seating, and a hot tub.

20. Jacuzzi year-round - Villa Luz Private Home

Hampon Bays

Annie B.

$1,085 nightly

Nov 13 - Nov 14

Total with taxes and fees

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Top Southold Hotel Reviews

A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.

Silver Sands Motel & Beach Bungalows

Greenport

10/10 Excellent

Nicole

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

The Shoals Suites and Slips

Southold

10/10 Excellent

Andrew

A rooftop deck with outdoor seating, fire pits, and a view of a body of water.

The Menhaden

Greenport

10/10 Excellent

Anonymous traveler

A spacious room with wicker furniture, large windows, and a view of the sea.

Sound View Greenport

Greenport

10/10 Excellent

Marilyn

Cliffside Resort Condominiums

Greenport

10/10 Excellent

Jeannine

A two-story house with a balcony, outdoor seating area, and a variety of plants.

Zey Hotel

Greenport

10/10 Excellent

Jennifer

A waterfront property with a large house, multiple boats docked, and lush greenery.

Sag Harbor Inn

Sag Harbor

10/10 Excellent

Anonymous traveler

The Harbor Front Inn

Greenport

10/10 Excellent

Maureen

A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.

House on Chase Creek

The Heights

10/10 Excellent

Damon

An outdoor patio area with string lights, tables, chairs, and a fire pit.

The Chequit

The Heights

10/10 Excellent

Joseph

A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

The Bentley Hotel Southampton

Southampton

10/10 Excellent

Jennifer

A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

Canoe Place Inn and Cottages

Hampton Bays

10/10 Excellent

Quinne

A marina at sunset with boats docked, a fire feature on the deck, and a chair.

Saybrook Point Resort & Marina

Old Saybrook Center

10/10 Excellent

Robin

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

The Hampton Maid

Hampton Bays

10/10 Excellent

Such a beautiful property, lots of trees, lovely landscaping. They keep Crassula in pots on all of the porches as long as weather permits. The room I stayed in (double queen) was very spacious. Wood beamed ceiling with a ceiling fan, walk in shower. Loved the restaurant that was open for breakfast daily. Open for dinner Tuesday - Saturday while I was there. It's still family owned and run after 69 years. Great dining options all around, and lots to see and do on the island - although you...

ALIX

A dining area with a fireplace, bookshelves, and a view of the bar area.

Bridgehampton Inn

Bridgehampton

10/10 Excellent

The Speights

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 $194 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.

Southold Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Southold vacation rentals

1. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

2. Cliffside Resort Condominiums

3. North Fork Resort

4. Harbor Heights

5. The SandPiper

6. Aqua Vista

7. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

8. Beach Block Hideaway

9. American Beech in Greenport - Petite King Room 7

10. Steps to the beach | Seabreeze Cottage #3

11. Northfork Townhouse walk to all

12. Cozy Cottage by the beach - Seabreeze #1

13. Renovated Townhouse walk to all

14. Beachfront Greenport Villa

15. Charming Accommodations in the Hamptons

16. 1-bedroom cottage with Grove Beach 🏖️ access.

17. Beachfront Jacuzzi All Year - Black Swan Home

18. Windward Shores Ocean Resort

19. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

20. Jacuzzi year-round - Villa Luz Private Home

Find vacation rentals that suit your style

Top Southold Hotel Reviews

Silver Sands Motel & Beach Bungalows

10/10 Excellent

Find out more about Southold

Everything you need to know about Southold vacation rentals

Southold vacation rentals: An excellent choice for every season

How to find incredible deals on Southold rentals

Frequently Asked Questions

Can I find a vacation rental in Southold?

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

How many vacation rentals are there in Southold?

What’s there to see and do in Southold?

What’s a vacation rental in Southold like?

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