What are the top rated Short Term Stays in Southold?

There are a lot of options in Southold. If you plan on staying in the Southold area, consider making a reservation for a few nights at one of these properties as these have been rated the top Short Term Stays in Southold: <a href="/property/southold-waterfront-with-boat-dock-boat-ramp-hot-tub-beaches/HA-321356134" class="class="static-page-link"">Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub &amp; Beaches</a> <a href="/property/private-coastal-two-bedroom-cottage-on-the-water/HA-3212535605" class="class="static-page-link"">Private Coastal Two Bedroom Cottage on the Water</a> <a href="/property/located-in-the-heart-of-wine-country-beaches-shops/HA-1214465665" class="class="static-page-link"">Located in the heart of wine country/BEACHES/shops.</a> <a href="/property/family-and-dog-friendly-getaway-near-amazing-wineries-beaches-and-restaurants/HA-3211551109" class="class="static-page-link"">Family and dog-friendly getaway near amazing wineries, beaches and restaurants!</a> <a href="/property/newly-renovated-gem-on-the-cedar-beach-peninsula/HA-3212243500" class="class="static-page-link"">Newly Renovated Gem on the Cedar Beach Peninsula!</a> <a href="/property/perfect-waterfront-family-vacation-home-next-to-the-best-vineyards-in-ny/HA-321356226" class="class="static-page-link"">Perfect Waterfront Family Vacation Home next to the best vineyards in NY!</a> <a href="/property/great-location-walk-to-town-train/HA-321759289" class="class="static-page-link"">Great Location! Walk to Town &amp; Train!</a> <a href="/property/charming-cottage/HA-3213126341" class="class="static-page-link"">Charming Cottage</a> <a href="/property/beachfront-endless-sunsets-sandy-beach-cozy-sunroom-open-concept-kitchen/HA-321896250" class="class="static-page-link"">Beachfront - endless sunsets, sandy beach, cozy sunroom &amp; open concept kitchen</a> <a href="/property/renovated-american-farmhouse-in-the-heart-of-southold-with-heated-saltwater-pool/HA-3212359920" class="class="static-page-link"">Renovated American Farmhouse in the heart of Southold with heated saltwater pool</a>

How much is rent for a furnished short-term stay in Southold?

At Corollavacationrentals short-term furnished accommodation in or near Southold ranges from $185 to $2,257 per night.

How many holiday rentals near Southold are available?

We have 5 places to stay near Southold. Check out the complete list of holiday rentals in Southold to find what works for your next trip.

Can we get a self-catering short-term stay in Southold?

Yes, there are 5 self-catering short-term rental homes in Southold that have hot tubs & other amenities The most popular self-catering top-rated rental homes are: Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay! Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable Serene bay front home with a private beach, deck, board games, & washer/dryer Lake House Located Near North Fork Wineries Happiness Comes in Waves The Shoals Suites and Slips Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

What are the best luxury short-term stays for families near Southold?

There are more than 5 luxury temporary places to stay near Southold, with other amenities available according to 2025 data from Corollavacationrentals.

Southold Short-Term Rentals

Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!

From US $543

10.0 (3 Reviews)

House

Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!

Air Conditioner
Parking
Pet Friendly

Southold Short-Term Vacation Rentals

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