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Southold Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Southold vacation rentals

Exterior
Beautifully farmhouse

Beautifully farmhouse

Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
$1,028 nightly
The price is $1,175
Jan 12 - Jan 13
Total with taxes and fees
Beautifully farmhouse
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$173 nightly
The price is $196
Jan 19 - Jan 20
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
$381 nightly
The price is $435
Jan 12 - Jan 13
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach
Smart TV, books
Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5)
"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.
$357 nightly
The price is $403
Jan 12 - Jan 13
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.

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (34)
"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.
Smart TV, fireplace, table tennis, books
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,479 nightly
The price is $7,402
Jan 9 - Jan 10
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Beach nearby
The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
East Lyme
9.0 out of 10, Wonderful, (4)
"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 9 - Jan 10
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Outdoor dining
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
9.6 out of 10, Exceptional, (22)
"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
Beach nearby, sun loungers, beach towels
Beach Cottage, private beach and pass

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (9)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
$352 nightly
The price is $398
Jan 13 - Jan 14
Total with taxes and fees
Beach Cottage, private beach and pass
Dining
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
Clinton
10.0 out of 10, Exceptional, (3)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
$471 nightly
The price is $533
Jan 13 - Jan 14
Total with taxes and fees
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
On the beach
Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
9.6 out of 10, Exceptional, (8)
"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
$173 nightly
The price is $196
Jan 9 - Jan 10
Total with taxes and fees
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
8.0 out of 10, Very Good, (2)
"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.
$173 nightly
The price is $196
Jan 9 - Jan 10
Total with taxes and fees
The Anchor at Soundview · Beach+Ocean+Sunrise
Interior
Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$384 nightly
The price is $434
Jan 11 - Jan 12
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
Westbrook
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$447 nightly
The price is $508
Jan 21 - Jan 22
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Exterior
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (41)
"Great property, would stay here again."
United States
charles b.
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,114 nightly
The price is $1,273
Jan 14 - Jan 15
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Beach
Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$396 nightly
The price is $452
Jan 20 - Jan 21
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the Beach
On the beach
The Bridge at Soundview · Beach+OceanView+Sunrise

The Bridge at Soundview · Beach+OceanView+Sunrise

The Bridge at Soundview · Beach+OceanView+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (2)
"Great space, large dining area, fully stocked kitchen, large bedrooms, great mattresses, ocean view from deck and one block from the ocean "
United States
Scott F.
$433 nightly
The price is $489
Jan 9 - Jan 10
Total with taxes and fees
The Bridge at Soundview · Beach+OceanView+Sunrise
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$219 nightly
The price is $250
Jan 11 - Jan 12
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Smart TV, books
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

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

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$508 nightly
The price is $580
Feb 5 - Feb 6
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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 Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Everything was Great Immaculate hotel very good location sraff was great"
latoya 1-night trip
Posted 3 days ago
The Harbor Front Inn

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.