We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

House holiday rentals in Southold

Find and book unique houses on Airbnb

Top-rated house rentals in Southold

Guests agree: These houses are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Home in Greenport

4.83 out of 5 average rating, 190 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

3 – 10 Apr

$5,779 AUD total

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

29 May – 5 June

$9,532 AUD total

Guest favourite

Home in Southold

5.0 out of 5 average rating, 17 reviews

Le Petit Cottage Southold NY

Experience the charm of a two-bedroom cottage in Southold, New York. Enjoy easy access to nearby South Harbor Park Beach, where you can swim and soak up the sun. Immerse yourself in the local wine scene with wineries just a short distance away. Explore nearby farms to savor fresh produce and artisanal goods. Unwind on the outdoor deck in the fresh North Fork air after a day of swimming, wine tasting and farm visits. Greenport and Shelter Island Ferry are a short ten minute drive away.

17 – 24 Apr

$2,677 AUD total

Guest favourite

Home in Southold

5.0 out of 5 average rating, 31 reviews

Salt & Sea House - Near wineries, farms, & beaches

Close to beaches, wineries, farms, and restaurants--the Salt and Sea House is a relaxing North Fork getaway for vacations and working from home. Uncork a bottle of wine, start up the barbecue, and settle into the beautiful scenery filled with trees and sounds of the sea. Highlights: * 3 min drive to Goose Creek Beach * 4 min drive to Croteaux Vineyards * 7 min drive to Country View farm * Master bath with tub and rain shower * Large fenced in yard * Pack & Play and toys

8 – 15 June

$5,015 AUD total

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

26 Feb – 5 Mar

$1,109 AUD total

Guest favourite

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

Built in 1928, this gorgeous home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The local wineries are all within short drives of this lovely retreat. Enjoy the new heated gunnite pool with plenty of poolside seating. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

10 – 17 Mar

$5,376 AUD total

Guest favourite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

9 – 16 Nov

$3,408 AUD total

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

24 Feb – 3 Mar

$9,663 AUD total

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 221 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

11 – 18 Aug

$6,352 AUD total

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 144 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

10 – 17 May

$8,606 AUD total

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 165 reviews

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.

4 – 11 Sept

$6,366 AUD total

Home in Westbrook

4.86 out of 5 average rating, 136 reviews

Family-Friendly Cottage by The Shore

Whether you’re simply traveling to the area or planning your next vacation, you’ve found the right place. Leave your worries behind and come enjoy our freshly updated home by the shore. With a clean, comfortable and convenient spot to stay you are free to explore & relax.

14 – 21 Oct

$2,409 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Southold house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

7 – 14 Aug

$9,401 AUD total

Guest favourite

Home in Manorville

4.99 out of 5 average rating, 200 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

13 – 20 Oct

$6,921 AUD total

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

30 Dec – 6 Jan

$10,218 AUD total

Guest favourite

Home in Southampton

4.87 out of 5 average rating, 237 reviews

Secluded Southampton Luxury Estate with tennis 288

24 – 31 Dec

$11,360 AUD total

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

2 – 9 Dec

$2,850 AUD total

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

23 – 30 Oct

$7,864 AUD total

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

24 Sept – 1 Oct

$12,690 AUD total

Guest favourite

Home in Watermill

4.88 out of 5 average rating, 128 reviews

Modern House close to the beach

19 – 26 Dec

$12,136 AUD total

Weekly house rentals

Guest favourite

Home in Cutchogue

4.97 out of 5 average rating, 31 reviews

Cozy Cottage with Views

6 – 13 Nov

$3,684 AUD total

Guest favourite

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

11 – 18 June

$7,443 AUD total

Guest favourite

Home in Southold

4.96 out of 5 average rating, 28 reviews

Bright Oasis in Beautiful North Fork Wine Country

1 – 8 Jan

$7,840 AUD total

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

8 – 15 Dec

$4,842 AUD total

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

9 – 16 Dec

$6,108 AUD total

Guest favourite

Home in Southold

4.89 out of 5 average rating, 19 reviews

Dockside Getaway in Southold NY

20 – 27 Feb

$6,573 AUD total

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 36 reviews

Beachfront Greenport Villa

12 – 19 Apr

$10,492 AUD total

Guest favourite

Home in Southold

5.0 out of 5 average rating, 32 reviews

Southold Comfort - North Fork Getaway

10 – 17 May

$8,563 AUD total

Private house rentals

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

24 Sept – 1 Oct

$6,646 AUD total

Guest favourite

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

23 – 30 Dec

$5,216 AUD total

Home in Greenport

4.91 out of 5 average rating, 54 reviews

Greenport Village Relaxation

12 – 19 May

$2,348 AUD total

Guest favourite

Home in Peconic

5.0 out of 5 average rating, 11 reviews

Coastal Cottage on the Water

4 – 11 Oct

$6,661 AUD total

Guest favourite

Home in Southold

4.97 out of 5 average rating, 78 reviews

Southold Beach house.

13 – 20 May

$5,103 AUD total

Home in Greenport

5.0 out of 5 average rating, 3 reviews

Waterfront Greenport Boathouse

6 – 13 Jan

$6,831 AUD total

Guest favourite

Home in Mattituck

4.92 out of 5 average rating, 61 reviews

Walk to Breakwater Beach in Heart of Wine Country

21 – 28 Oct

$5,776 AUD total

Guest favourite

Home in Greenport

4.99 out of 5 average rating, 71 reviews

Beach House in L.I. Wine Country

24 – 31 Oct

$5,477 AUD total

Quick stats about house rentals in Southold

Total rentals
170 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
160 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
$153 AUD before taxes and fees

Destinations to explore