Southold Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Southold vacation rentals

Exterior

Vacation Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3 reviews)
"good experience"
United States
Anonymous traveler
The price is ￥94,914
￥185,794 total
includes taxes & fees
Jan 22 - Jan 23
Beautifully farmhouse
Smart TV, fireplace, table tennis, books

Vacation Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is ￥663,164
￥1,170,278 total
includes taxes & fees
Jan 22 - Jan 23
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Smart TV

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1 review)
The price is ￥8,700
￥71,751 total
includes taxes & fees
Jan 29 - Jan 30
Seabreeze #3: Cozy Cottage by the beach
On the beach

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
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 ￥14,243
￥33,275 total
includes taxes & fees
Jan 22 - Jan 23
The Stern at Soundview · Beach+Ocean+Sunrise
Smart TV, books

Vacation 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 ￥15,874
￥66,227 total
includes taxes & fees
Jan 26 - Jan 27
Rogers Lake House (87) · CT College+Beach+USCGA
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 ￥26,908
￥63,192 total
includes taxes & fees
Jan 23 - Jan 24
Beach Cottage, private beach and pass
1 bedroom, desk, iron/ironing board, travel crib

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.6 out of 10, Exceptional, (34 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥13,763
￥29,724 total
includes taxes & fees
Jan 23 - Jan 24
1-bedroom cottage with Grove Beach 🏖️ access.
Interior

Vacation Home in Bay Point

Sag Harbor Water View w Dock 1.5ml from town
The price is ￥711,855
￥1,007,403 total
includes taxes & fees
Jan 24 - Jan 25
Sag Harbor Water View w Dock 1.5ml from town
Beach nearby

Vacation Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
9.0 out of 10, Wonderful, (4 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.
The price is ￥18,728
￥57,632 total
includes taxes & fees
Jan 22 - Jan 23
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Private kitchen

Condo in Hampton Bays

Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is ￥189,726
￥229,767 total
includes taxes & fees
Jan 22 - Jan 23
Canoe Place Waterfront Residences
Dining

Vacation Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is ￥21,197
￥81,997 total
includes taxes & fees
Feb 10 - Feb 11
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Outdoor dining

Vacation Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥15,661
￥211,458 total
includes taxes & fees
Jan 22 - Jan 23
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Beach

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥23,665
￥82,463 total
includes taxes & fees
Jan 27 - Jan 28
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop

Vacation 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.
The price is ￥15,661
￥154,708 total
includes taxes & fees
Feb 8 - Feb 9
Blackberry: Private home with jacuzzi year-round
Terrace/patio

Vacation Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ￥23,729
￥201,338 total
includes taxes & fees
Jan 25 - Jan 26
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Smart TV, fireplace

Vacation Home in Sag Harbor

Spacious 5-bedroom house with water views and 2 houses from the bay.
The price is ￥632,760
￥1,001,438 total
includes taxes & fees
Jan 26 - Jan 27
Spacious 5-bedroom house with water views and 2 houses from the bay.
Property grounds

Vacation 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 ￥28,474
￥57,106 total
includes taxes & fees
Jan 22 - Jan 23
Stylish Modern Stay Steps from the Ocean
Property grounds

Cabin in Killingworth

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (54 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is ￥71,186
￥129,914 total
includes taxes & fees
Jan 22 - Jan 23
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Private kitchen

Apartment in Essex

Quintessential Essex. Steps from the Steam Train!
2.0 star property
The price is ￥25,184
￥48,735 total
includes taxes & fees
Jan 23 - Jan 24
Quintessential Essex. Steps from the Steam Train!
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 Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Nice"
Valerie 1-night trip
Posted 23 hours ago
The Bentley Hotel Southampton

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:

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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?

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 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, 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.