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Southold Vacation Rentals

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Check prices for these dates

Tonight
Dec 7 - Dec 8
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Dec 8 - Dec 9
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Vacation Rentals in Southold

On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
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
The price is ￥11,811
￥30,033 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

10.0 out of 10, Exceptional, (1)
The price is ￥8,543
￥70,454 total
includes taxes & fees
Dec 14 - Dec 15
Seabreeze #3: Cozy Cottage by the beach
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

10.0 out of 10, Exceptional, (4)
"Communication was excellent. "
United States
Katy C.
The price is ￥13,413
￥62,545 total
includes taxes & fees
Dec 8 - Dec 9
Rogers Lake House (87) · CT College+Beach+USCGA
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Vacation Home in 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.
The price is ￥634,119
￥1,127,503 total
includes taxes & fees
Dec 8 - Dec 9
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

2.0 star property
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.
The price is ￥18,216
￥56,396 total
includes taxes & fees
Dec 8 - Dec 9
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is ￥9,506
￥26,007 total
includes taxes & fees
Dec 9 - Dec 10
1-bedroom cottage with Grove Beach 🏖️ access.
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥20,333
￥77,477 total
includes taxes & fees
Dec 9 - Dec 10
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

9.0 out of 10, Wonderful, (4)
"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.
The price is ￥11,650
￥136,826 total
includes taxes & fees
Dec 15 - Dec 16
Blackberry: Private home with jacuzzi year-round
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in 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.
The price is ￥15,378
￥197,518 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
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.
The price is ￥11,811
￥30,033 total
includes taxes & fees
Dec 9 - Dec 10
The Anchor at Soundview · Beach+Ocean+Sunrise
Private kitchen
Stylish Modern Stay Steps from the Ocean

Vacation Home in Clinton

10.0 out of 10, Exceptional, (1)
"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.
The price is ￥27,959
￥56,074 total
includes taxes & fees
Dec 8 - Dec 9
Stylish Modern Stay Steps from the Ocean
Fridge, microwave, oven, stovetop
Adorable Cottage, 5 min walk to water & town

Vacation Home in Westbrook Center

9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥27,003
￥64,683 total
includes taxes & fees
Dec 8 - Dec 9
Adorable Cottage, 5 min walk to water & town
Fridge, microwave, stovetop, dishwasher
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Cottage in 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.
The price is ￥35,726
￥81,637 total
includes taxes & fees
Dec 9 - Dec 10
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Fridge, microwave, oven, stovetop
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Cottage in Old Saybrook Center

9.6 out of 10, Exceptional, (39)
"Great property, would stay here again."
United States
charles b.
The price is ￥38,199
￥79,111 total
includes taxes & fees
Dec 8 - Dec 9
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Exterior
Shoreline Oasis

Apartment in Clinton

9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is ￥27,804
￥40,479 total
includes taxes & fees
Dec 8 - Dec 9
Shoreline Oasis
On the beach
The Bridge at Soundview · Beach+OceanView+Sunrise

Apartment in Old Lyme

2.0 star property
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
United States
Emotional J.
The price is ￥19,819
￥75,746 total
includes taxes & fees
Dec 8 - Dec 9
The Bridge at Soundview · Beach+OceanView+Sunrise
Terrace/patio
American Beech in Greenport - Petite King Room 7

Vacation Home in Greenport

9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
The price is ￥27,804
￥42,949 total
includes taxes & fees
Dec 8 - Dec 9
American Beech in Greenport - Petite King Room 7
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Vacation Home in Saybrook Manor

9.6 out of 10, Exceptional, (133)
"Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back. "
United States
Rob C.
The price is ￥31,066
￥79,995 total
includes taxes & fees
Dec 22 - Dec 23
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
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 Sagaponack

The Sagaponack

10/10 Excellent
"Everything was amazing! Friendly service! "
Kim 3-night trip
Posted 3 days ago
The Sagaponack

Find out more about Southold

Search for holiday rentals in Southold on Expedia! You can easily find your home rentals, villas, holiday apartments in Southold using one of the methods below:

  • View our selection of featured holiday rentals in Southold
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Look no further and take a look at our great range of rental properties in Southold!

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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?

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub: You might want to consider this vacation home rental near Southold, which is located by the ocean and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 9 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 123 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, The Old Field Vineyards and Sparkling Pointe 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.