Town of Southold Town Holiday Rentals from NZ$436: 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 holiday rentals

1. Cliffside Resort Condominiums

Greenport

William

includes taxes & fees

12 Nov - 13 Nov

A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

Greenport

Altynai

includes taxes & fees

25 Oct - 26 Oct

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

3. Aqua Vista

Pipes Cove

Kerri L.

includes taxes & fees

9 Nov - 10 Nov

A beach with people relaxing on chairs and sunbathing.

4. Harbor Heights

Pipes Cove

Steven R.

includes taxes & fees

2 Nov - 3 Nov

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

5. The SandPiper

Pipes Cove

Manuela C.

includes taxes & fees

10 Nov - 11 Nov

A beach with people relaxing, a pier extending into the water, and a clear sky.

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

Pipes Cove

"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"

Nino

includes taxes & fees

2 Nov - 3 Nov

A wooden pathway leading to a beach with scattered rocks and greenery.

7. Beach Block Hideaway

Pipes Cove

Teresa C.

includes taxes & fees

4 Nov - 5 Nov

An outdoor dining area with hanging lights, palm trees, and a bar.

8. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

includes taxes & fees

25 Oct - 26 Oct

A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

9. Beachfront Greenport Villa

Greenport

Kate R.

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a sofa, coffee table, and dining area.

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

Greenport

Jeannette M.

includes taxes & fees

16 Nov - 17 Nov

A rocky beach with clear water and a forested hillside in the background.

11. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

Mattituck

Glenn F.

includes taxes & fees

24 Oct - 25 Oct

A wooden interior with a staircase, a blue sofa, and a fireplace.

12. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

Mattituck

william p.

includes taxes & fees

17 Nov - 18 Nov

A modern dining area with a wooden table, white chairs, and a chandelier.

13. Northfork Townhouse walk to all

Greenport

Beth R.

includes taxes & fees

27 Oct - 28 Oct

A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

14. Renovated Townhouse walk to all

Greenport

Liz H.

includes taxes & fees

17 Nov - 18 Nov

An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

15. American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

includes taxes & fees

29 Oct - 30 Oct

A spacious hallway with high ceilings, arched columns, and chandeliers.

16. Montauk Manor

Montauk

Maria

includes taxes & fees

17 Nov - 18 Nov

17. Windward Shores Ocean Resort

Napeague

Banessa

includes taxes & fees

3 Nov - 4 Nov

18. Driftwood Resort

Montauk

Julian

includes taxes & fees

25 Oct - 26 Oct

19. Montauk Oceanside Suites

Downtown Montauk

Jadana

includes taxes & fees

25 Oct - 26 Oct

A wooden counter with a Dove beauty bar, Tommy Hilfiger towels, and a black hair dryer bag.

20. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

includes taxes & fees

26 Oct - 27 Oct

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Top Town of Southold Town Hotel Reviews

Zey Hotel

10/10 Excellent

"The hotel had a good vibe and energy! Lots of artwork and was very charming. It has a bed and breakfast feel to it. The parking is behind the hotel and free and convenient. It’s right on Main Street and walking distance to all restaurants and bars. The staff especially James was warm and friendly and accommodating. We had a great time checking out all the cool lounge areas in the hotel. The room was clean and charming as well. Would definitely stay here again the next time we visit Greenport"

The Harbor Front Inn

8/10 Good

"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue we will continue to stay here because it is a very nice hotel"

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

10/10 Excellent

"The house sells itself, but Robert greeting us as we walked the dogs to the beach was very nice. We chatted a bit and he made sure we understood the rules of the rental and the rest of our stay was great. We drove from DC to attend my nephew’s wedding at nearby Sound View, so the location was excellent.The house had everything we needed: quiet, comfort and simple. We will gladly stay here again and may look into renting the larger house on the property if our group contains more than four people.So great that Robert welcomes dogs. Our dogs and humans loved the beach. The rooms were clean with great views. Washer and Dryer are fairly new and worked great. We loved the bagels and sandwiches at Goldberg’s Bagels.Maybe next time we will have time to share a beer or coffee with Robert on the patio."

Find out more about Town of Southold Town

Everything you need to know about Town of Southold Town holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Southold Town holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Southold Town holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Town of Southold Town holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Southold Town. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Southold Town holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Town of Southold Town holiday rentals we have selected for you start as low as NZ$436 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Southold Town rentals

At Expedia, we put the best Town of Southold Town holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Town of Southold Town rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Southold Town holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Southold Town. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Town of Southold Town holiday rentals

1. Cliffside Resort Condominiums

2. North Fork Resort

3. Aqua Vista

4. Harbor Heights

5. The SandPiper

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

7. Beach Block Hideaway

8. American Beech in Greenport - Petite King Room 7

9. Beachfront Greenport Villa

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

11. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

12. Breakwater Estate: Heated Saltwater Pool, Sleeps 12

13. Northfork Townhouse walk to all

14. Renovated Townhouse walk to all

15. American Beech in Greenport - Deluxe King 6

16. Montauk Manor

17. Windward Shores Ocean Resort

18. Driftwood Resort

19. Montauk Oceanside Suites

20. 1-bedroom cottage with Grove Beach 🏖️ access.

Find holiday rentals that suit your style

Top Town of Southold Town Hotel Reviews

Zey Hotel

North Fork Resort

The Harbor Front Inn

The SandPiper

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

The Menhaden

Cliffside Resort Condominiums

Aqua Vista

Beach Block Hideaway

Find out more about Town of Southold Town