Photo by Benny Goh

Southold Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Jan 14 - Jan 15
Tomorrow
Jan 15 - Jan 16
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Our top choices for Southold vacation rentals

Exterior
Beautifully farmhouse

Vacation Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3 reviews)
"good experience"
United States
Anonymous traveler
$1,028 nightly
The price is $1,175
Jan 15 - Jan 16
Total with taxes and fees
Beautifully farmhouse
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1 review)
$395 nightly
The price is $451
Jan 15 - Jan 16
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
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
$172 nightly
The price is $194
Jan 20 - Jan 21
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV, books
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
$356 nightly
The price is $403
Jan 20 - Jan 21
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
1 bedroom, desk, iron/ironing board, travel crib
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
$157 nightly
The price is $178
Jan 21 - Jan 22
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Beach nearby, sun loungers, beach towels
Beach Cottage, private beach and pass

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
Jan 15 - Jan 16
Total with taxes and fees
Beach Cottage, private beach and pass
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

Blackberry: Private home with jacuzzi year-round
9.0 out of 10, Wonderful, (4 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.
$856 nightly
The price is $978
Feb 8 - Feb 9
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Smart TV, books
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Cottage in Greenport

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$536 nightly
The price is $612
Feb 5 - Feb 6
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Beach nearby
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
9.0 out of 10, Wonderful, (4 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.
$308 nightly
The price is $348
Jan 16 - Jan 17
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Beach
Seabreeze #4: Charming Cottage Footsteps to the Beach

Cottage in Hampton Bays

Seabreeze #4: Charming Cottage Footsteps to the Beach
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$389 nightly
The price is $444
Jan 20 - Jan 21
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the Beach
Outdoor dining
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
9.6 out of 10, Exceptional, (22 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,170 nightly
The price is $1,337
Jan 20 - Jan 21
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,110 nightly
The price is $1,268
Jan 15 - Jan 16
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
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.
$442 nightly
The price is $501
Jan 20 - Jan 21
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Interior
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Vacation Home in Saybrook Manor

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (134 reviews)
"We loved our stay!"
United States
Deana L.
$456 nightly
The price is $516
Jan 15 - Jan 16
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
On the beach
Freeboard at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.6 out of 10, Exceptional, (8 reviews)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
United States
Dana
$172 nightly
The price is $194
Jan 20 - Jan 21
Total with taxes and fees
Freeboard at Soundview · Beach+Ocean+Sunrise
Interior
Adorable Cottage, 5 min walk to water & town

Vacation Home in Westbrook Center

Adorable Cottage, 5 min walk to water & town
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$386 nightly
The price is $436
Jan 15 - Jan 16
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Dining
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Vacation Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
$479 nightly
The price is $543
Jan 19 - Jan 20
Total with taxes and fees
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Anchor at Soundview · Beach+Ocean+Sunrise
2.0 star property
8.0 out of 10, Very Good, (2 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
$172 nightly
The price is $194
Jan 18 - Jan 19
Total with taxes and fees
The Anchor at Soundview · Beach+Ocean+Sunrise
Property grounds
Stylish Modern Stay Steps from the Ocean

Vacation Home in Clinton

Stylish Modern Stay Steps from the Ocean
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
$298 nightly
The price is $337
Jan 15 - Jan 16
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
Terrace/patio
American Beech in Greenport - Petite King Room 7

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.
$198 nightly
The price is $226
Jan 15 - Jan 16
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

Spark by Hilton Guilford

Spark by Hilton Guilford

10/10 Excellent
"Clean room and building. Pleasant and efficient staff. Would stay there again."
Amber 1-night trip
Posted 2 days ago
Spark by Hilton Guilford

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 $850 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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr: You might want to consider this vacation home 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 116 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 Corey Creek Winery 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.