Southold Vacation Homes

A calm lake with a forest in the background during sunset.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Southold holiday homes

1. Aqua Vista

Pipes Cove

Kerri L.

HK$2,490 total

includes taxes & fees

7 Oct - 8 Oct

2. The SandPiper

Pipes Cove

Timothy

HK$2,826 total

includes taxes & fees

10 Sept - 11 Sept

3. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

HK$3,336 total

includes taxes & fees

10 Sept - 11 Sept

4. Beach Block Hideaway

Pipes Cove

Teresa C.

HK$3,278 total

includes taxes & fees

14 Sept - 15 Sept

5. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

HK$2,705 total

includes taxes & fees

9 Sept - 10 Sept

6. Northfork Townhouse walk to all

Greenport

Beth R.

HK$6,171 total

includes taxes & fees

9 Sept - 10 Sept

7. Black Swan Beachfront Home with Jacuzzi year round

Hampton Bays

Donald J.

HK$9,393 total

includes taxes & fees

9 Sept - 10 Sept

8. Renovated Townhouse walk to all

Greenport

Melissa A.

HK$5,208 total

includes taxes & fees

9 Sept - 10 Sept

9. Adorable Cottage, 5 min walk to water & town

Westbrook Center

Donovan V.

HK$3,795 total

includes taxes & fees

9 Sept - 10 Sept

10. Beachfront Greenport Villa

Greenport

Kate R.

HK$10,851 total

includes taxes & fees

10 Sept - 11 Sept

11. BlackBerry Private home with jacuzzi yearlong

East Hampton

Suzanne R.

HK$10,361 total

includes taxes & fees

9 Sept - 10 Sept

12. Villa Luz Family Home w/ heated pool & jacuzzi

Hampon Bays

Carola C.

HK$13,159 total

includes taxes & fees

9 Sept - 10 Sept

13. Work and Play Special! Extended Stay Discount

Shelter Island

Kathleen Andrews K.

HK$10,435 total

includes taxes & fees

22 Sept - 23 Sept

14. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

maria m.

HK$8,733 total

includes taxes & fees

9 Sept - 10 Sept

15. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton

Robert R.

HK$4,604 total

includes taxes & fees

22 Sept - 23 Sept

16. Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

Shannon G.

HK$4,531 total

includes taxes & fees

9 Sept - 10 Sept

17. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme

Emily M.

HK$2,300 total

includes taxes & fees

6 Oct - 7 Oct

18. American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

HK$3,422 total

includes taxes & fees

17 Sept - 18 Sept

19. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Sag Harbor

Nadja B.

HK$11,259 total

includes taxes & fees

13 Sept - 14 Sept

20. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Sag Harbor

HK$15,003 total

includes taxes & fees

9 Sept - 10 Sept

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Southold Hotel Reviews

Zey Hotel

10/10 Excellent

"AMAZING SPOT"

The Hampton Maid

10/10 Excellent

"Our stay at The Hampton Maid was such a great choice. The entire hotel is absolutely charming—you can tell that every corner and every detail has been thoughtfully designed. The front desk staff was wonderful: so friendly, welcoming, and very clear with all the information. We loved the bungalow-style rooms, each with its own deck and parking, which gives you wonderful privacy between rooms. But what truly stole our hearts was the gorgeous, beautifully kept garden—a true green oasis that brings complete peace and lets you fully disconnect from city stress. The room was spotless, and the restaurant was phenomenal—we had breakfast there, and it was spectacular. On top of that, getting a pass to 7 local beaches for just $5 is an incredible perk. You really couldn't ask for more! It’s one of those places where you haven't even left yet, and you're already planning your return. Can't wait to go back!"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, no-frills property! I look forward to staying here once again!"

Saybrook Point Resort & Marina

10/10 Excellent

"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."

Sound View Greenport

10/10 Excellent

"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city and enjoy some quiet time by the water. Greenport is also nearby, making it convenient to explore the local restaurants, shops, vineyards, and other attractions. If you’re planning a trip to Greenport or the North Fork, Sound View is definitely a place worth considering. I would happily stay here again! 🌅🌊❤️"

Find out more about Southold