Southold Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
22 Aug - 24 Aug
Next weekend
29 Aug - 31 Aug

Holiday Rentals in Southold

Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (238)
"Great location, great views. Walls are a little thin."
The price is HK$2,586
HK$3,294 total
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (291)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is HK$1,303
HK$1,658 total
includes taxes & fees
14 Sept - 15 Sept
Windward Shores Ocean Resort
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Great place! Great communication with property owner!"
The price is HK$2,316
HK$4,402 total
includes taxes & fees
21 Aug - 22 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Terrace/patio

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

The price is HK$1,754
HK$2,280 total
includes taxes & fees
1 Sept - 2 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (93)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

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! "
The price is HK$603
HK$1,535 total
includes taxes & fees
2 Sept - 3 Sept
The Stern at Soundview · Beach+Ocean+Sunrise
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is HK$1,950
HK$3,131 total
includes taxes & fees
25 Aug - 26 Aug
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Sag Harbor Suite by the Beach
1 bedroom, WiFi, bed sheets

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (29)
"Amazing property! Had all the things we needed "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Shoreline Oasis
Exterior

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!"
The price is HK$1,396
HK$2,032 total
includes taxes & fees
26 Aug - 27 Aug
Shoreline Oasis
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is HK$2,332
HK$5,587 total
includes taxes & fees
21 Aug - 22 Aug
Southampton cozy cottage by the beach
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
On the beach

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

10 Bedroom Hampton House with a regulation size Pickleball court

9.8 out of 10, Exceptional, (30)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball court
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (71)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (40)
"My wife and I loved our weekend stay at this cabin!"
The price is HK$2,632
HK$5,164 total
includes taxes & fees
26 Aug - 27 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
Exterior

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.0 out of 10, Wonderful, (4)
"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. "
The price is HK$563
HK$1,473 total
includes taxes & fees
26 Aug - 27 Aug
Freeboard at Soundview · Beach+Ocean+Sunrise
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
Sign in
Sign up, it's free

Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Spacious, super clean, and functional suites. The staff is super diligent and friendly. The property is kept very well, there is an ample back yard with tables and benches, dog potty supplies. This area is super cozy and lit up at night. The bed and linens were SUPER nice and comfortable. There is very good lighting in the room all over and the A/C worked perfectly. We are so happy we decided to stay here."
Teresa 1-night trip
Posted 1 day ago
Pier Blue Inn Old Saybrook - Essex

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Southold offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Southold?

With 124 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.