Southold Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Southold holiday rentals

Beach nearby

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
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
The price is HK$745
HK$1,692 total
includes taxes & fees
1 Mar - 2 Mar
The Stern at Soundview · Beach+Ocean+Sunrise
Beach nearby, sun-loungers, beach towels

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.
The price is HK$1,331
HK$3,125 total
includes taxes & fees
3 Mar - 4 Mar
Beach Cottage, private beach and pass
1 bedroom, desk, iron/ironing board, travel cot

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is HK$739
HK$1,538 total
includes taxes & fees
1 Mar - 2 Mar
1-bedroom cottage with Grove Beach 🏖️ access.
Fridge, microwave, oven, stovetop

Cottage in Clinton

The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is HK$1,000
HK$2,044 total
includes taxes & fees
2 Mar - 3 Mar
The gardners Cottage 1 mile from long Island Sound - pet friendly
Terrace/patio

Cottage in Pipes Cove

Cottage on Beach front Estate with Dockage .Walk to Village
9.8 out of 10, Exceptional, (77 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
Cottage on Beach front Estate with Dockage .Walk to Village
Individually decorated, individually furnished, iron/ironing board

Aparthotel in Napeague

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (306 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is HK$1,117
HK$1,489 total
includes taxes & fees
1 Mar - 2 Mar
Windward Shores Ocean Resort
Smart TV, books

Holiday 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.
The price is HK$1,108
HK$3,692 total
includes taxes & fees
3 Mar - 4 Mar
Rogers Lake House (87) · CT College+Beach+USCGA
Exterior detail

Holiday Home in Calverton

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is HK$3,513
HK$6,579 total
includes taxes & fees
1 Mar - 2 Mar
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
1 bedroom, free WiFi, bed sheets

Apartment in East Quogue

Hamptons apartment getaway
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is HK$1,174
HK$2,252 total
includes taxes & fees
1 Mar - 2 Mar
Hamptons apartment getaway
Terrace/patio

Holiday 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.
The price is HK$931
HK$1,573 total
includes taxes & fees
1 Mar - 2 Mar
American Beech in Greenport - Petite King Room 7
Property grounds

Cabin in Killingworth

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (55 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is HK$3,520
HK$6,425 total
includes taxes & fees
1 Mar - 2 Mar
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Terrace/patio

Holiday Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Dining

Holiday Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is HK$845
HK$3,853 total
includes taxes & fees
4 Mar - 5 Mar
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Fridge, microwave, oven, stovetop

Holiday 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.
Blackberry: Private home with jacuzzi year-round
Exterior

Cottage in Old Saybrook Center

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
9.6 out of 10, Exceptional, (43 reviews)
"Great property, would stay here again."
United States
charles b.
The price is HK$1,790
HK$3,815 total
includes taxes & fees
3 Mar - 4 Mar
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Interior

Holiday Home in Southampton

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
9.2 out of 10, Wonderful, (11 reviews)
"Great location. Great host. Easy house, pool and private back yard. It's modest but has it all."
United States
Harry V.
The price is HK$1,373
HK$4,760 total
includes taxes & fees
1 Mar - 2 Mar
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Interior

Houseboat in Old Lyme

Floating Nest on Private River. Serene Views & Ultimate Relaxation
The price is HK$1,760
HK$2,938 total
includes taxes & fees
21 Mar - 22 Mar
Floating Nest on Private River. Serene Views & Ultimate Relaxation
1 bedroom, desk, iron/ironing board, travel cot

Apartment in Westbrook Center

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
The price is HK$785
HK$2,264 total
includes taxes & fees
1 Mar - 2 Mar
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Property grounds

Holiday 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.
The price is HK$1,408
HK$2,824 total
includes taxes & fees
10 Mar - 11 Mar
Stylish Modern Stay Steps from the Ocean
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
"Enjoyed our stay. Clean room , temperature in room was cozy, bed was comfortable and snack bar in main house was a nice touch."
Susan 1-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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  • Enter your travel dates to view the best deals on holiday rentals in Southold while they last

Look no further and take a look at our great range of rental properties in Southold!

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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This holiday home rental outside of Southold is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Southold?

With 120 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?

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 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.