Vacation Homes in Southold, NY
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Top Vacation Homes in Southold

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Stunning Hampton Holiday Family Fantasy for your Team

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

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

Exquisite New Hampton Home in a Perfect Location

Brand New Beach House In Amagansett

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Another rental season is coming up.
Top hotels in Southold

The Shoals Suites and Slips
Find the Best Vacation Homes in Southold
Why book a vacation home in Southold?
Vacation homes in Southold make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Southold?
Private Southold rental homes range between $114 - $590 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Southold vacation home rentals. You might look for Southold rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Southold offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Southold?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Southold. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Southold hotels and vacation homes that best suit your stay. We also have deals for flights, and Southold car rentals. You’ll save even more when you bundle your items into a Southold vacation package!
How many vacation homes are available to book in Southold?
There are 1926 rental homes in Southold. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Southold?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Southold Vacation Homes essential information
Accommodation | 1926 Vacation Homes |
---|---|
Lowest Price | $114 |
Highest Price | $590 |
Popular accommodation | Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor , Stunning Hampton Holiday Family Fantasy for your Team , Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!, Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!, Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen, Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living, Exquisite New Hampton Home in a Perfect Location, Brand New Beach House In Amagansett, The Cooper-Burke House, Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, Another rental season is coming up., Charming beach home, complete with pool & cozy guest house! |
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