Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA

Southold Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Southold vacation rentals

1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (46 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
$220 nightly
The price is $249
Jun 26 - Jun 27
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, books

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (8 reviews)
"We had a very nice stay at Roger’s Lake! The house was so cool! It had all the amenities we needed and the location was charming and peaceful. In particular, the beds are really comfortable! They have this awesome exercise room where you can stretch out and enjoy the light. The host, Peter, was especially easy to work with and was very communicative. My family and I are hoping to come back soon for another stay."
United States
Andrea
$417 nightly
The price is $472
Jun 23 - Jun 24
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$463 nightly
The price is $495
Jun 28 - Jun 29
Total with taxes and fees
Seabreeze 4 Charming Cottage footsteps to beach
Living area

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Old Lyme
$186 nightly
The price is $210
Jun 21 - Jun 22
Total with taxes and fees
Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (23 reviews)
$352 nightly
The price is $402
Jun 23 - Jun 24
Total with taxes and fees
North Fork Resort
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
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
$243 nightly
The price is $275
Jun 21 - Jun 22
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Shower, hair dryer, towels, shampoo

Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (24 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$2,566 nightly
The price is $2,759
Jul 6 - Jul 7
Total with taxes and fees
Villa Luz Family Home w/ heated pool & jacuzzi
1 bedroom, bed sheets

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
$259 nightly
The price is $296
Jun 22 - Jun 23
Total with taxes and fees
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
$260 nightly
The price is $298
Jun 21 - Jun 22
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (258 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
$287 nightly
The price is $328
Jun 23 - Jun 24
Total with taxes and fees
Cliffside Resort Condominiums
Beach nearby

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"This is a must property for any vacationer traveling to Long Island. You will fall in love with quiet evenings after delightful beach walks. Don’t forget the therapeutic ocean air! Within very short walking distance, you are near The Pavilion and the famous Kokomo’s Restaurant. Kokomo’s is the best ocean restaurant in Old Lyme for a reason, with fantastic ocean views and an unmatched family dining experience. As Old Lyme begins its long-awaited restoration project, this beach apartment will...
United States
Jennivere
$260 nightly
The price is $293
Jun 21 - Jun 22
Total with taxes and fees
Keel at Soundview · Beach+OceanView+Sunrise
Beach nearby

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
$260 nightly
The price is $294
Jun 21 - Jun 22
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$301 nightly
The price is $344
Jun 23 - Jun 24
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
8.8 out of 10, Excellent, (6 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.
$432 nightly
The price is $487
Jun 23 - Jun 24
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
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.
$1,077 nightly
The price is $1,149
Jun 28 - Jun 29
Total with taxes and fees
BlackBerry Private home with jacuzzi yearlong
1 bedroom, bed sheets

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
$296 nightly
The price is $338
Jun 28 - Jun 29
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
Smart TV, offices

Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
$464 nightly
The price is $496
Jun 28 - Jun 29
Total with taxes and fees
Seabreeze #3 Cozy Cottage steps to the beach
Beach nearby, sun loungers, beach towels

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
$581 nightly
The price is $657
Jul 6 - Jul 7
Total with taxes and fees
Beach Cottage, private beach and pass
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (316 reviews)
"Nice homey room"
United States
Andrew
$313 nightly
The price is $358
Jun 25 - Jun 26
Total with taxes and fees
Windward Shores Ocean Resort
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (138 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
$629 nightly
The price is $712
Jun 22 - Jun 23
Total with taxes and fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Great hotel &staff. Perfect location to explore the east end of Long Island."
Michael 3-night trip
Posted 1 hour ago
Hyatt Place Long Island East End

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 $249 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?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: You might want to consider this vacation home rental near Southold, which is located in the city center and has an outdoor pool, a fireplace, 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 balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Southold?

With 118 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, Sparkling Pointe and The Old Field Vineyards 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.