Southold vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Southold
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold vacation rentals
Stay near Southold's top sights
Other great vacation rentals in Southold
Cottage in Southold
4.89 out of 5 average rating, 19 reviewsQuaint Cottage Close to LI Sound
Nov 15 – 22
Home in Cutchogue
4.96 out of 5 average rating, 74 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Jan 19 – 26
Home in Southold
4.96 out of 5 average rating, 26 reviewsBright Oasis in Beautiful North Fork Wine Country
May 2 – 9
Guest suite in Cutchogue
4.9 out of 5 average rating, 83 reviewsEnjoy a relaxing getaway to the North Fork
Sep 1 – 8
Cottage in Southold
4.95 out of 5 average rating, 21 reviewsAdorable Cottage
May 6 – 13
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
Jun 11 – 18
Cottage in Southold
4.94 out of 5 average rating, 32 reviewsBordeaux meets Côte d’Azur—1763 Historic Farmhouse
Sep 26 – Oct 3
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
May 29 – Jun 5
Other great vacation rentals in Southold
Home in Southold
5.0 out of 5 average rating, 25 reviewsGreenport walk to beach & vineyard! Brand new home
Feb 20 – 27
Home in Greenport
5.0 out of 5 average rating, 29 reviewsHistoric Stunner in Heart of Village
Jun 14 – 21
Home in East Marion
4.83 out of 5 average rating, 6 reviewsPrivate North Fork Cottage- Walk to Beach!
Sep 7 – 14
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Oct 20 – 27
Home in Southold
5.0 out of 5 average rating, 19 reviewsHorton House
Nov 23 – 30
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Feb 1 – 8
Home in Southold
5.0 out of 5 average rating, 32 reviewsSouthold Comfort - North Fork Getaway
Jul 9 – 16
Home in Southold
4.89 out of 5 average rating, 19 reviewsDockside Getaway in Southold NY
Oct 28 – Nov 4
Quick stats about vacation rentals in Southold
Total rentals
220 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
€ 94 before taxes and fees
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Southold?
Yes! Work meets play with ease at over 120 vacation rentals in Southold featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Southold?
Four-legged friends are welcome in Southold. Choose from more than 80 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Southold?
Experience the best of Southold with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Southold house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 house rentals with pools in Southold, available on Airbnb. Make a splash and soak up the sun in style!
Do cottage rentals in Southold have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have self check-in?
Absolutely! We offer over 50 house rentals with self check-in in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have wifi?
Absolutely! We offer over 170 house rentals with wifi in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have a gym?
Absolutely! We offer over 30 house rentals with a gym in Southold. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Southold?
Southold has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cottage Rentals in Southold?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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