Town of Southold Town Vacation Rentals

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An aerial view of a harbor with boats, a ship, and a dock extending into the water.
Vacation RentalsVacation Rentals
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Greenport

Greenport
A calm lake with a forest in the background during sunset.
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Vacation RentalsVacation Rentals

Southold

Southold

Town of Southold Town Vacation Rentals

North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
$470 nightly
The price is $537 total per night
$537 total
Aug 4 - Aug 5
Total with taxes and fees
North Fork Resort features free WiFi in public areas, a seasonal outdoor pool, and laundry facilities. If you decide to drive, there's free parking. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include barbecue grills, a gift shop, and a picnic area.
Pool
Pet friendly
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
$452 nightly
The price is $516 total per night
$516 total
Aug 5 - Aug 6
Total with taxes and fees
Guests of Cliffside Resort Condominiums enjoy features like a private beach, free WiFi in public areas, and a seasonal outdoor pool. If you plan to drive, free parking is available. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this beach aparthotel include a terrace, laundry facilities, and a vending machine.
Pool
Kitchen
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

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

greenport NY
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

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

Southold NY
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Aqua Vista

Aqua Vista

Greenport, NY
$566 nightly
The price is $647 total per night
$647 total
Aug 30 - Aug 31
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Spacious 5 Bedroom Family Beach Getaway in Charming East Marion/Greenport

Spacious 5 Bedroom Family Beach Getaway in Charming East Marion/Greenport

East Marion NY
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
Renovated Townhouse walk to all

Renovated Townhouse walk to all

Greenport NY
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Peconic NY
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Gorgeous Historical 6 bdrm House close to vineyards and breweries,

Gorgeous Historical 6 bdrm House close to vineyards and breweries,

Peconic NY
Guests staying at this vacation home have access to barbecue grills and a garden.
Kitchen
Free WiFi
Beach, Pool, Wine, Shopping!

Beach, Pool, Wine, Shopping!

Mattituck NY
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
Pool
Kitchen
Northfork Townhouse walk to all

Northfork Townhouse walk to all

Greenport NY
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The SandPiper

The SandPiper

Greenport, NY
$566 nightly
The price is $647 total per night
$647 total
Aug 16 - Aug 17
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

Orient NY
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Greenport NY
$1,679 nightly
The price is $1,918 total per night
$1,918 total
Aug 9 - Aug 10
Total with taxes and fees
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport NY
$450 nightly
The price is $514 total per night
$514 total
Aug 2 - Aug 3
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Harbor Heights

Harbor Heights

Greenport NY
$521 nightly
The price is $595 total per night
$595 total
Aug 12 - Aug 13
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Washer
Dryer
Historic House Getaway

Historic House Getaway

Peconic NY
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden.
Elevated North Fork Escape with Chic Interiors and Private Poolside Oasis -...

Elevated North Fork Escape with Chic Interiors and Private Poolside Oasis -...

Cutchogue NY
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Town of Southold Town

    North Fork Resort

    North Fork Resort

    690 Queen St Greenport NY
    $470 nightly
    The price is $537 total per night from Aug 4 to Aug 5
    $537 total
    Aug 4 - Aug 5
    Total with taxes and fees
    9.4/10 Exceptional! (41 reviews)
    Zey Hotel

    Zey Hotel

    439 Main Street Greenport NY
    $243 nightly
    The price is $278 total per night from Aug 17 to Aug 18
    $278 total
    Aug 17 - Aug 18
    Total with taxes and fees
    9.2/10 Wonderful! (364 reviews)
    Sound View Greenport

    Sound View Greenport

    58775 County Rd 48 Greenport NY
    $387 nightly
    The price is $442 total per night from Aug 18 to Aug 19
    $442 total
    Aug 18 - Aug 19
    Total with taxes and fees
    8.4/10 Very Good! (672 reviews)

Orbitz makes it easy to find vacation rentals in Town of Southold Town 

🏠 What is the best price for a Town of Southold Town vacation rental?


Town of Southold Town rentals range between $278 and $1,918 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Town of Southold Town can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Town of Southold Town getaway. Orbitz filters your search results so you can find the best Town of Southold Town vacation rental for you. We have tons of options.


🏠 Are cancellations free on Town of Southold Town vacation rentals with Orbitz?


You may be able to cancel or amend your Town of Southold Town vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Town of Southold Town?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Town of Southold Town by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Town of Southold Town?


When you book a Town of Southold Town vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Town of Southold Town?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Town of Southold Town—with plenty of hidden gems. We also have plenty of inventory in Town of Southold Town main cities and near popular attraction spots.


🏠 Why should I book my Town of Southold Town vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Town of Southold Town vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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