Southold Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Southold vacation rentals

Beach nearby, sun loungers, beach towels

Cottage in East Lyme

Beach Cottage, private beach and pass
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
$353 nightly
The price is $399
Mar 8 - Mar 9
Total with taxes and fees
Beach Cottage, private beach and pass
1 bedroom, desk, iron/ironing board, travel crib

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (38 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$159 nightly
The price is $180
Mar 10 - Mar 11
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Beach nearby

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$218 nightly
The price is $244
Mar 28 - Mar 29
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Individually decorated, individually furnished, iron/ironing board

Aparthotel in Napeague

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (309 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
$167 nightly
The price is $190
Mar 8 - Mar 9
Total with taxes and fees
Windward Shores Ocean Resort
Smart TV, books

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5 reviews)
"Communication was excellent. "
United States
Katy C.
$417 nightly
The price is $469
Mar 8 - Mar 9
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Dining

Vacation Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
$431 nightly
The price is $488
Mar 8 - Mar 9
Total with taxes and fees
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets

Cottage in Greenport

North Fork Cottages & RV Resort
3.0 star property
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
$259 nightly
The price is $296
Apr 5 - Apr 6
Total with taxes and fees
North Fork Cottages & RV Resort
Terrace/patio

Vacation Home in Hampton Bays

Black Swan Beachfront Home with Jacuzzi year round
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$802 nightly
The price is $885
Mar 8 - Mar 9
Total with taxes and fees
Black Swan Beachfront Home with Jacuzzi year round
Property grounds

Cabin in Killingworth

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (55 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
$726 nightly
The price is $821
Mar 8 - Mar 9
Total with taxes and fees
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
1 bedroom, free WiFi, bed sheets

Apartment in East Quogue

Hamptons apartment getaway
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
$252 nightly
The price is $288
Mar 8 - Mar 9
Total with taxes and fees
Hamptons apartment getaway
Exterior detail

Apartment in Clinton

Shoreline Oasis
9.2 out of 10, Wonderful, (7 reviews)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
$229 nightly
The price is $260
Mar 31 - Apr 1
Total with taxes and fees
Shoreline Oasis
Exterior detail

Vacation Home in Calverton

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
8.6 out of 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."
United States
Nicole A.
$736 nightly
The price is $841
Mar 8 - Mar 9
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Terrace/patio

Vacation Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$176 nightly
The price is $201
Mar 8 - Mar 9
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Dining

Vacation Home in East Hampton North

Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
$647 nightly
The price is $690
Mar 15 - Mar 16
Total with taxes and fees
Designer East Hampton Farmhouse Bike to Amagansett, Ocean Beaches, Seasonal Pool
Beach nearby

Apartment in Westbrook Center

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
$343 nightly
The price is $386
Mar 8 - Mar 9
Total with taxes and fees
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Condo | Terrace/patio

Aparthotel in Greenport

Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
$211 nightly
The price is $241
Mar 22 - Mar 23
Total with taxes and fees
Cliffside Resort Condominiums
Interior

Houseboat in Old Lyme

Floating Nest on Private River. Serene Views & Ultimate Relaxation
$332 nightly
The price is $376
Mar 21 - Mar 22
Total with taxes and fees
Floating Nest on Private River. Serene Views & Ultimate Relaxation
Smart TV, fireplace

Vacation Home in Greenport

Renovated Townhouse walk to all
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
$479 nightly
The price is $547
Mar 8 - Mar 9
Total with taxes and fees
Renovated Townhouse walk to all
Beach

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
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.
$471 nightly
The price is $533
Mar 11 - Mar 12
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Dining

Vacation Home in Greenport

Northfork Townhouse walk to all
10.0 out of 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"
United States
Beth R.
$541 nightly
The price is $618
Mar 8 - Mar 9
Total with taxes and fees
Northfork 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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Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"This was my first time at Water’s Edge and will definitely not be my last. Our stay was wonderful. Becky at the front desk was "
Jenifer 1-night trip
Posted 7 hours ago
Water's Edge Resort & Spa

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 $180 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.

Explore a world of travel with Expedia

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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: Visitors like this Southold vacation home rental. It 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 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Southold?

With 119 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?

Horton Lane Beach and McCabe's Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Croteaux Vineyards and Osprey's Dominion 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.