Compare Southold Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Southold Cottages

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3 out of 5
690 Queen St Greenport NY
North Fork Cottages & RV Resort features free WiFi in public areas, a seasonal outdoor pool, and laundry facilities. If you decide to drive, there's free parking. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include a picnic area, barbecue grills, and a gift shop.
Pool
Pet friendly
'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 of this cottage enjoy access to a water park, laundry facilities, and a garden. This beach cottage also has barbecue grills.
Kitchen
Washer
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

Westbrook CT
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This family-friendly cottage also has barbecue grills.
Pool
Hot Tub
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
Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach

Hampton Bays NY
$390 nightly
The price is $446 total per night
$446 total
Jan 12 - Jan 13
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Dryer
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
Lovely Cottage in the Heart of Long Island Wine country

Lovely Cottage in the Heart of Long Island Wine country

Southold NY
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Free WiFi
Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town

Westbrook CT
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
Don't see what you're looking for?
See all available properties in Southold
View all properties
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
    $165 nightly
    The price is $189 total per night from Feb 1 to Feb 2
    $189 total
    Feb 1 - Feb 2
    Total with taxes and fees
    9.4/10 Exceptional! (232 reviews)
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road Westbrook CT
    $244 nightly
    The price is $281 total per night from Jan 4 to Jan 5
    $281 total
    Jan 4 - Jan 5
    Total with taxes and fees
    8.8/10 Excellent! (1,001 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $75 nightly
    The price is $86 total per night from Jan 4 to Jan 5
    $86 total
    Jan 4 - Jan 5
    Total with taxes and fees
    7.8/10 Good! (1,001 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
193 Cottages
Lowest Price
$86
Highest Price
$446
Popular accommodation
North Fork Cottages & RV Resort, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston., Direct waterfront renovated cottage. , Seabreeze #3: Cozy Cottage by the beach, The gardners Cottage 1 mile from long Island Sound - pet friendly, Totally Renovated Cottage on the North Fork 7 min. walk to the Beach, Lovely Cottage in the Heart of Long Island Wine country, Adorable Cottage with Cottage porch, walk to water & town

Explore More Ways to Travel with Travelocity