Compare Southold Vacation Rentals

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Southold Rentals

Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

2.53 mi from city center
Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. This family-friendly cottage also has barbecue grills.
Kitchen
Washer
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
3.13 mi from city center
$326 nightly
The price is $372 total per night
$372 total
Oct 26 - Oct 27
Total with 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, a picnic area, and a vending machine.
Pool
Kitchen
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

6.92 mi from city center
Guests staying at this vacation home enjoy a gym, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Pool
Kitchen
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 out of 5
9.88 mi from city center
$356 nightly
The price is $406 total per night
$406 total
Oct 1 - Oct 2
Total with taxes and fees
Guests staying at this vacation home enjoy an outdoor pool, a hot tub, and barbecue grills. Additional amenities include a garden and a water dispenser.
Pool
Hot Tub
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
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.61 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Hot Tub
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

13.06 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 beach vacation home include barbecue grills and a garden.
Hot Tub
Kitchen
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2 out of 5
15.02 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Washer
Dryer
Shoreline Oasis

Shoreline Oasis

15.61 mi from city center
$232 nightly
The price is $263 total per night
$263 total
Oct 5 - Oct 6
Total with 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
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

18.94 mi from city center
$266 nightly
The price is $301 total per night
$301 total
Oct 1 - Oct 2
Total with taxes and fees
At this houseboat, guests have access to barbecue grills.
Kitchen
Free WiFi
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

19.8 mi from city center
$615 nightly
The price is $696 total per night
$696 total
Oct 6 - Oct 7
Total with taxes and fees
At this cabin, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly cabin also has a garden.
Kitchen
Washer
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
$151 nightly
The price is $172 total per night
$172 total
Oct 19 - Oct 20
Total with 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 $172 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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