Town of Southold Town Vacation Rentals from ￥57,239: Search Short-Term Rentals

A white colonial-style house with a green roof and a lighthouse tower.

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Our top choices for Town of Southold Town vacation rentals

1. North Fork Resort

Greenport

Lisa

￥57,239 total

includes taxes & fees

Sep 14 - Sep 15

2. Cliffside Resort Condominiums

Greenport

Christine

￥70,058 total

includes taxes & fees

Sep 9 - Sep 10

3. The SandPiper

Pipes Cove

Marie H.

￥59,945 total

includes taxes & fees

Sep 10 - Sep 11

4. Aqua Vista

Pipes Cove

Molly G.

￥59,945 total

includes taxes & fees

Sep 8 - Sep 9

5. Harbor Heights

Pipes Cove

Nigel

￥61,219 total

includes taxes & fees

Sep 13 - Sep 14

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

Pipes Cove

Callie E.

￥82,352 total

includes taxes & fees

Sep 7 - Sep 8

7. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

￥71,603 total

includes taxes & fees

Sep 8 - Sep 9

8. Beach Block Hideaway

Pipes Cove

maureen f.

￥87,413 total

includes taxes & fees

Sep 8 - Sep 9

9. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

￥187,298 total

includes taxes & fees

Sep 14 - Sep 15

10. Beachfront Greenport Villa

Greenport

patricia m.

￥242,048 total

includes taxes & fees

Sep 10 - Sep 11

11. American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

￥81,947 total

includes taxes & fees

Sep 7 - Sep 8

1 bedroom, desk, iron/ironing board, travel crib

12. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

￥35,916 total

includes taxes & fees

Sep 8 - Sep 9

Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

13. Driftwood Resort

Montauk

William

￥47,865 total

includes taxes & fees

Sep 13 - Sep 14

14. Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Norwich

Aura

￥45,633 total

includes taxes & fees

Sep 8 - Sep 9

15. Montauk Manor

Montauk

Amelia

￥57,234 total

includes taxes & fees

Sep 7 - Sep 8

16. The Tiny Cottage & Mini Farm

Oakdale,

Jeffrey H.

￥25,473 total

includes taxes & fees

Aug 17 - Aug 18

17. Cozy Studio: Indoor Hot Tub & Inground Pool Access

Montville

Eduardo

￥68,495 total

includes taxes & fees

Aug 26 - Aug 27

18. Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

New London

Vicente B.

￥22,984 total

includes taxes & fees

Aug 24 - Aug 25

19. Cozy Corner, by the Spa

Norwich

Troy

￥52,707 total

includes taxes & fees

Sep 8 - Sep 9

20. A Mystic Stay as Sweet as Apple Pie!

Old Mystic

Logan

￥39,934 total

includes taxes & fees

Aug 16 - Aug 17

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Top Town of Southold Town Hotel Reviews

The Shoals Suites and Slips

10/10 Excellent

"The hotel was very clean with a lovely environment. The staff (especially at the front desk) were helpful, friendly, polite and very knowledgeable about recommendations for the area. The property was well maintained and the views were beautiful and very accessible to many activities in the area. Looking forward to return in the near future."

North Fork Resort

10/10 Excellent

"The property was so clean, charming, and exceeded all expectations. The whole staff was so lovely and helped solve every issue above and beyond! We got locked out of our room and the front desk was closed but there was an after hours number that we were able to call and they virtually unlocked our door. So make sure you ask for that! And when our firewood took too long to be delivered, Vanessa generously offered to extend our stay an hour and refunded us for the logs. Melissa and Christine also were great and helpful at answering our questions! So special and we would stay again!"

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

8/10 Good

"Pat is a wonderful owner with a lovely property that sits at the end of the road. The backyard is what he refers to as a creek. There are a few canoes that you could use for recreation or to get to the local public beach. There are many bicycles available. When we were there in early August, there were several gnats/bugs and it was very humid. I wish there would’ve been a pool or at least some lounge chairs with shade. His beach umbrella was broken. Overall, he was a pleasure to work with and there are many vineyards to choose from."

The Menhaden

10/10 Excellent

"Definitely stay here! A perfect location, walkable to so many cute restaurants and shops. Beautiful water view from the rooftop. Most comfortable bed and gorgeous, clean room. And the icing on the cake (almost literally!) is the snack room on each floor with fresh baked cookies, fresh juices, chips, candies and more. They make a wonderful espresso martini at the bar too. We hope to be back!"

Beach, Pool, Wine, Shopping!

10/10 Excellent

"Property was in a perfect spot for getting around the North Shore and over to the Hampton as well. Plenty of room and the back cottage can accommodate another couple/small family. Lived the outdoor space and the surrounding area. Definitely would come back here again - AND the owners were super easy to work with and very quick to respond to our questions!"

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Vacation Apartments in Town of Southold Town

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Change your mind

Treat yourself

Be picky

Our top choices for Town of Southold Town vacation rentals

1. North Fork Resort

2. Cliffside Resort Condominiums

3. The SandPiper

4. Aqua Vista

5. Harbor Heights

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

7. American Beech in Greenport - Petite King Room 7

8. Beach Block Hideaway

9. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

10. Beachfront Greenport Villa

11. American Beech in Greenport - Deluxe King 6

12. 1-bedroom cottage with Grove Beach 🏖️ access.

13. Driftwood Resort

14. Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

15. Montauk Manor

16. The Tiny Cottage & Mini Farm

17. Cozy Studio: Indoor Hot Tub & Inground Pool Access

18. Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

19. Cozy Corner, by the Spa

20. A Mystic Stay as Sweet as Apple Pie!

Find vacation rentals that suit your style

Top Town of Southold Town Hotel Reviews

The Shoals Suites and Slips

North Fork Resort

Aqua Vista

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Charming Mattituck Retreat Near the Bay with Modern Updates

The Harbor Front Inn

The Menhaden

Beach, Pool, Wine, Shopping!

Cliffside Resort Condominiums

Find out more about Town of Southold Town

Vacation Apartments in Town of Southold Town

Go further with the Expedia app

Vacation Rentals in Town of Southold Town

Change your mind

Treat yourself

Be picky

Our top choices for Town of Southold Town vacation rentals

1. North Fork Resort

2. Cliffside Resort Condominiums

3. The SandPiper

4. Aqua Vista

5. Harbor Heights

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

7. American Beech in Greenport - Petite King Room 7

8. Beach Block Hideaway

9. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

10. Beachfront Greenport Villa

11. American Beech in Greenport - Deluxe King 6

12. 1-bedroom cottage with Grove Beach 🏖️ access.

13. Driftwood Resort

14. Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

15. Montauk Manor

16. The Tiny Cottage & Mini Farm

17. Cozy Studio: Indoor Hot Tub & Inground Pool Access

18. Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

19. Cozy Corner, by the Spa

20. A Mystic Stay as Sweet as Apple Pie!

Find vacation rentals that suit your style

Top Town of Southold Town Hotel Reviews

The Shoals Suites and Slips

Find out more about Town of Southold Town

Vacation Apartments in Town of Southold Town

Go further with the Expedia app