Compare Southold Cottage Rentals

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Featured Cottages in Southold

North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
$222 nightly
The price is $254 total per night
$254 total
Oct 4 - Oct 5
Total with taxes and fees
North Fork Resort features free WiFi in public areas, a seasonal outdoor pool, and laundry facilities. If you decide to drive, there's free parking. Additional amenities include barbecue grills, a gift shop, and a picnic area.
Pool
Pet friendly
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
$202 nightly
The price is $229 total per night
$229 total
Oct 26 - Oct 27
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Air conditioning
Cottage on Beach front Estate Walk to Village

Cottage on Beach front Estate Walk to Village

greenport NY
At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.
Kitchen
Washer
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue NY
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

greenport NY
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Peconic NY
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton CT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Direct waterfront renovated cottage.

Direct waterfront renovated cottage.

Madison CT
At this cottage, guests have access to features like laundry facilities. This beach cottage also has a garden.
Kitchen
Washer
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

3 out of 5
Madison CT
This cottage features free WiFi in public areas and barbecue grills. If you decide to drive, there's free parking.
Kitchen
Parking included
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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 Southold

    The Shoals Suites and Slips

    The Shoals Suites and Slips

    61600 Main Rd Southold NY
    $227 nightly
    The price is $256 total per night from Nov 1 to Nov 2
    $256 total
    Nov 1 - Nov 2
    Total with taxes and fees
    9.4/10 Exceptional! (344 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $78 nightly
    The price is $90 total per night from Oct 7 to Oct 8
    $90 total
    Oct 7 - Oct 8
    Total with taxes and fees
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road Westbrook CT
    $193 nightly
    The price is $222 total per night from Nov 1 to Nov 2
    $222 total
    Nov 1 - Nov 2
    Total with taxes and fees
    8.8/10 Excellent! (1,013 reviews)

Cottages

Book a cottage in Southold
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Southold. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Southold better.

Cottage apartments in Southold range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Southold
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Southold and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Southold cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Southold. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Southold Cottages essential information

Accommodation
197 Cottages
Lowest Price
$90
Highest Price
$256
Popular accommodation
North Fork Resort, 1-bedroom cottage with Grove Beach 🏖️ access., Cottage on Beach front Estate Walk to Village, Totally Renovated Cottage on the North Fork 7 min. walk to the Beach, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Fabulous Waterfront Property in the Heart of Wine Country, Cozy cottage near downtown Clinton, Marina & Hammonasset Park, Direct waterfront renovated cottage. , 2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

More to Explore