Photo by gavvykins

Town of Southold Town Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Town of Southold Town holiday rentals

9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$451
includes taxes & fees
1 Jan - 2 Jan 2026
American Beech in Greenport - Petite King Room 7
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 AU$783
includes taxes & fees
7 Jan - 8 Jan 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is AU$995
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Northfork Townhouse- walk to all

Holiday Home in Greenport

Beachfront Greenport Villa
9.6 out of 10, Exceptional, (10)
"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"
United States
Melissa F.
Beachfront Greenport Villa

Holiday Home in Southold

Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveller
The price is AU$1,773
includes taxes & fees
6 Jan - 7 Jan 2026
Beautifully farmhouse
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
Northfork Townhouse- walk to all/ newly renovated
2.0 out of 10, (1)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is AU$578
includes taxes & fees
12 Jan - 13 Jan 2026
American Beech in Greenport - Deluxe King 6

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1276)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is AU$266
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor
2.0 star property
10.0 out of 10, Exceptional, (2)
"Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! "
United States
jeff
The price is AU$196
includes taxes & fees
1 Jan - 2 Jan 2026
The Tiny Cottage at Clem & Clyde's
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 AU$292
includes taxes & fees
3 Jan - 4 Jan 2026
The Stern at Soundview · Beach+Ocean+Sunrise
9.8 out of 10, Exceptional, (192)
"There were stunning views, it was very relaxing, and we had excellent communication with the host. We couldn’t be happier, it was perfect! Kayaking was the best part. Plenty to see and do in the area as well."
United States
Heather S.
The price is AU$407
includes taxes & fees
4 Jan - 5 Jan 2026
Lakeside cottage ON the water with beautiful views up the lake!
10.0 out of 10, Exceptional, (27)
"Everything was perfect! Great location, easy check in/out, great amenities in room, and super comfy bed. "
United States
Paul S.
The price is AU$299
includes taxes & fees
13 Jan - 14 Jan 2026
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
10.0 out of 10, Exceptional, (10)
"Nice location, easy access to downtown Mystic. Nice compliment of amenities. "
United States
Karen B.
The price is AU$294
includes taxes & fees
25 Jan - 26 Jan 2026
Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium
9.8 out of 10, Exceptional, (220)
"Very comfortable, easy to get to and had everything you could need in a house rental! "
United States
Anna K.
The price is AU$393
includes taxes & fees
5 Jan - 6 Jan 2026
Lakeside cottage overhanging the water, beautiful window views across the lake
9.6 out of 10, Exceptional, (82)
"Beautiful, cozy, little apartment walking distance from downtown Mystic! Well kept and perfect for a quick 2 night trip!Thank you - would definitely stay here again! "
United States
Clayton H.
The price is AU$259
includes taxes & fees
5 Jan - 6 Jan 2026
Super Cute & Cozy Apartment in Downtown Mystic!

Holiday Home in Old Mystic

A Mystic Stay as Sweet as Apple Pie!
2.0 star property
10.0 out of 10, Exceptional, (7)
"Loved the personal touches!"
United States
Jenny
The price is AU$325
includes taxes & fees
13 Jan - 14 Jan 2026
A Mystic Stay as Sweet as Apple Pie!
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is AU$277
includes taxes & fees
10 Jan - 11 Jan 2026
1-bedroom cottage with Grove Beach 🏖️ access.
9.8 out of 10, Exceptional, (16)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is AU$382
includes taxes & fees
4 Jan - 5 Jan 2026
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
10.0 out of 10, Exceptional, (7)
"We had a good experience staying with host, William. Going in and out of our unit was easy with the codes provided. The croissants provided for breakfast were large and delicious. We would stay there again."
United States
Ronald H.
The price is AU$184
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is AU$557
includes taxes & fees
5 Jan - 6 Jan 2026
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Town of Southold Town Hotel Reviews

Find out more about Town of Southold Town

Everything you need to know about Town of Southold Town 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 Town of Southold Town 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 Town of Southold Town holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Town of Southold Town holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Southold Town. 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 Town of Southold Town 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 Town of Southold Town holiday rentals we have chosen for you start as low as AU$451 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Town of Southold Town rentals

At Expedia, we put the best Town of Southold Town 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 Town of Southold Town 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 Town of Southold Town 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 Town of Southold Town. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.