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Southold Rentals

Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
3.13 mi from city center
$287 nightly
The price is $328 total per night
$328 total
Jul 9 - Jul 10
Total includes taxes and fees
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, barbecue grills, and a picnic area.
Pool
Kitchen
Escape to Sag Harbor

Escape to Sag Harbor

7.92 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a gym, and laundry facilities. Additional amenities include a garden and barbecue grills.
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Lovely North Fork Beach Cottage (2 BR/2 bath)!

9.73 mi from city center
Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. Transportation is made easy with limo/town car service. This family-friendly cottage also has barbecue grills.
Fairy Tale Guest Cottage in Magic Garden by Pool

Fairy Tale Guest Cottage in Magic Garden by Pool

10.88 mi from city center
At this cottage, guests have access to an outdoor pool and a garden.
Pool
Kitchen
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

4 out of 5
239 E Montauk Hwy, Hampton Bays, NY
12.91 mi from city center
At Canoe Place Waterfront Residences, guests access to a full-service spa, a seasonal outdoor pool, and a garden. Free parking is included with your stay. The 24-hour front desk has staff always at the ready. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls.
Pool
Kitchen
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

13.35 mi from city center
At this vacation home, guests have access to a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
adorable ranch in beach community

adorable ranch in beach community

14.19 mi from city center
$571 nightly
The price is $646 total per night
$646 total
Jul 9 - Jul 10
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Hamptons Retreat

Hamptons Retreat

13.68 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a gym, and laundry facilities. Additional amenities include a garden and barbecue grills.
Pool
Kitchen
Perfect Mid-Century Private Waterfront East Hampton Retreat!

Perfect Mid-Century Private Waterfront East Hampton Retreat!

13.64 mi from city center
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden. This beach vacation home also has barbecue grills.
Shoreline Oasis

Shoreline Oasis

15.61 mi from city center
$230 nightly
The price is $261 total per night
$261 total
Jul 9 - Jul 10
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise

2 out of 5
17.16 mi from city center
$173 nightly
The price is $195 total per night
$195 total
Jul 10 - Jul 11
Total includes taxes and fees
This apartment is a smoke-free apartment building.
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
20.6 mi from city center
$354 nightly
The price is $404 total per night
$404 total
Jul 9 - Jul 10
Total includes taxes and fees
Guests of Windward Shores Ocean Resort enjoy outdoor tennis courts, free WiFi in public areas, and a seasonal outdoor pool. Free parking is included with your stay. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Other amenities at this beach aparthotel include free newspapers, a terrace, and laundry facilities.
Pool
Kitchen
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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.

Southold Large Group Rentals

How to Book Vacation Rentals in Southold



🏠 What is the best price for Southold vacation rentals?

Southold vacation rentals range in price, starting at $195 per night.


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

Orbitz offers a wide range of Southold rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Southold condo rentals.


🏠 Is it free to cancel my Southold vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Southold vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Southold. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


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

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Southold apartments and enjoy an extended stay.


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

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Southold package deals will get you even more savings.

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