Town of Southold Town Vacation Rentals

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Top cities in Town of Southold Town

Beautiful spot on the #longisland sound surfing
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Greenport

Greenport
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Southold

Southold

Town of Southold Town Vacation Rentals

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3 out of 5
690 Queen St Greenport NY
North Fork Cottages & RV 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 a gift shop, a picnic area, and barbecue grills.
Pool
Pet friendly
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
At Cliffside Resort Condominiums, guests have access to free WiFi in public areas, a seasonal outdoor pool, and a terrace. 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 laundry facilities, a picnic area, and barbecue grills.
Pool
Kitchen
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Peconic NY
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills. This family-friendly cottage also has a garden.
Kitchen
Washer
Aqua Vista

Aqua Vista

Greenport, NY
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

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

Greenport, NY
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Hot Tub
Kitchen
The SandPiper

The SandPiper

Greenport, NY
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Surrounded by nature, come stay in this 1 bedroom private, serene location

Surrounded by nature, come stay in this 1 bedroom private, serene location

Southold NY
At this vacation home, guests have access to features like laundry facilities.
Washer
Dryer
Newly Constructed 3-bedroom Modern Farmhouse - walk to Greenport Village!

Newly Constructed 3-bedroom Modern Farmhouse - walk to Greenport Village!

Greenport NY
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Washer
Dryer
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport NY
$217 nightly
The price is $248 total per night
$248 total
Dec 22 - Dec 23
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Breakfast included
Dryer
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport NY
This condo offers a water park, an outdoor pool, and laundry facilities. Other amenities at this beach condo building include barbecue grills and a garden.
Pool
Kitchen
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

Southold NY
Guests staying at this vacation home enjoy a water park, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Hot Tub
Kitchen
New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Greenport NY
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
NEW VICTORIAN GEM IN GREENPORT

NEW VICTORIAN GEM IN GREENPORT

Greenport NY
At this vacation home, guests have access to an outdoor pool and a garden.
Pool
Kitchen
Beautifully farmhouse

Beautifully farmhouse

Southold NY
$1,028 nightly
The price is $1,175 total per night
$1,175 total
Dec 22 - Dec 23
Total with taxes and fees
Guests of this vacation home enjoy access to a water park, laundry facilities, and a garden.
Kitchen
Washer
“Paradise Found” - Walk to Private Beach & In-Ground Pool!

“Paradise Found” - Walk to Private Beach & In-Ground Pool!

2 out of 5
Southold NY
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds,...

Peconic NY
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Pool
Kitchen
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families

Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families

Greenport NY
Guests of this vacation home enjoy features like a gym, a hot tub, and laundry facilities. This smoke-free vacation home also has barbecue grills.
Pool
Hot Tub
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!

Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!

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

    The Shoals Suites and Slips

    The Shoals Suites and Slips

    61600 Main Rd Southold NY
    $169 nightly
    The price is $194 total per night from Dec 29 to Dec 30
    $194 total
    Dec 29 - Dec 30
    Total with taxes and fees
    9.4/10 Exceptional! (228 reviews)
    The Harbor Front Inn

    The Harbor Front Inn

    209 Front St Greenport NY
    $178 nightly
    The price is $203 total per night from Jan 19 to Jan 20
    $203 total
    Jan 19 - Jan 20, 2026
    Total with taxes and fees
    8.8/10 Excellent! (547 reviews)
    Sound View Greenport

    Sound View Greenport

    58775 County Rd 48 Greenport NY
    $202 nightly
    The price is $231 total per night from Dec 22 to Dec 23
    $231 total
    Dec 22 - Dec 23
    Total with taxes and fees
    8.4/10 Very Good! (598 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 $194 and $1,175 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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