Southold Holiday Rentals

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Holiday Rentals in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
Anonymous traveller
The price is AU$1,798
includes taxes & fees
23 Oct - 24 Oct
Beautifully farmhouse
New Construction full of amenities
2.0 star property
The price is AU$1,201
includes taxes & fees
18 Oct - 19 Oct
New Construction full of amenities
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (243)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
dean
The price is AU$461
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
The Stern at Soundview · Beach+Ocean+Sunrise
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! "
Lylian
The price is AU$258
includes taxes & fees
19 Oct - 20 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (33)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
michelle
The price is AU$277
includes taxes & fees
21 Oct - 22 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (2)
"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!"
Hemie J.
The price is AU$627
includes taxes & fees
11 Nov - 12 Nov
Rogers Lake House (87) · CT College+Beach+USCGA
Hidden gem! Southampton beach cottage
10.0 out of 10, Exceptional, (1)
The price is AU$699
includes taxes & fees
26 Oct - 27 Oct
Hidden gem! Southampton beach cottage
The Mast at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
Nora M.
The price is AU$258
includes taxes & fees
22 Oct - 23 Oct
The Mast at Soundview · Beach+Ocean+Sunrise
Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.4 out of 10, Exceptional, (6)
"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. "
Dana
The price is AU$258
includes taxes & fees
19 Oct - 20 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise
Insta-worthy Couples Retreat: Perfect for romantic getaway!
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
Ellen C.
The price is AU$397
includes taxes & fees
29 Oct - 30 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Cozy quiet gem, private & fenced in backyard
9.4 out of 10, Exceptional, (3)
"good times"
Mary M.
The price is AU$1,413
includes taxes & fees
20 Oct - 21 Oct
Cozy quiet gem, private & fenced in backyard
The Anchor at Soundview · Beach+Ocean+Sunrise
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. "
October P.
The price is AU$256
includes taxes & fees
19 Oct - 20 Oct
The Anchor at Soundview · Beach+Ocean+Sunrise
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"Great job "
emilio
The price is AU$472
includes taxes & fees
27 Oct - 28 Oct
American Beech in Greenport - Petite King Room 7
The King 1BR Beachside Home | Tennis+Ocean+WiFiPKG
10.0 out of 10, Exceptional, (1)
The price is AU$1,005
includes taxes & fees
19 Oct - 20 Oct
The King 1BR Beachside Home | Tennis+Ocean+WiFiPKG
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
James S.
The price is AU$597
includes taxes & fees
27 Oct - 28 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
Jeannette M.
The price is AU$885
includes taxes & fees
20 Oct - 21 Oct
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Forecastle at Soundview · Beach+OceanView+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (1)
"The location is perfect, just a few houses from the beach. The unit has a great view, very clean and new. The owners/managers were very prompt and communicative. I was VERY hesitant to book a place without reviews- but this was an excellent choice. The beach is clean and private, people are friendly. I will happily stay again!"
megan g.
The price is AU$314
includes taxes & fees
19 Oct - 20 Oct
Forecastle at Soundview · Beach+OceanView+Sunrise
Southampton cozy cottage by the beach
10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
Weston B.
The price is AU$712
includes taxes & fees
20 Oct - 21 Oct
Southampton cozy cottage by the beach
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
Julie
The price is AU$404
includes taxes & fees
23 Oct - 24 Oct
Shoreline Oasis
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
2.0 star property
9.0 out of 10, Wonderful, (4)
"Very nice place and super responsive host. "
Angelo D.
The price is AU$915
includes taxes & fees
19 Oct - 20 Oct
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
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

Find out more about Southold

Everything you need to know about Southold holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southold holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southold holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southold holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southold holiday rentals we have selected for you start as low as AU$258 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southold rentals

At Expedia, we put the best Southold holiday 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 holiday.

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 holiday rental in Southold?

Yes, there are holiday rentals in Southold close to Custer Institute and Observatory, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Southold has to offer?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This holiday home rental outside of Southold is located near the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Southold?

With 125 Expedia holiday rentals, you're guaranteed 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 holiday rental in Southold like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Southold. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.