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
$257 nightly
The price is $293 total per night
$293 total
May 28 - May 29
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. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include a gift shop, barbecue grills, and a picnic area.
Pool
Pet friendly
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
$165 nightly
The price is $187 total per night
$187 total
May 28 - May 29
Total with taxes and fees
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Air conditioning
'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, barbecue grills, and a garden.
Kitchen
Washer
Fairy Tale Guest Cottage in Magic Garden by Pool

Fairy Tale Guest Cottage in Magic Garden by Pool

Bridgehampton NY
At this cottage, guests have access to an outdoor pool and a garden.
Pool
Free WiFi
Cozy & Warm Getaway Cottage in Beach Community

Cozy & Warm Getaway Cottage in Beach Community

Niantic CT
At this cottage, guests have access to a gym, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

Water Mill NY
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
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
NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access

Clinton CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Washer
Dryer
Beach Cottage, private beach and pass

Beach Cottage, private beach and pass

East Lyme CT
$615 nightly
The price is $696 total per night
$696 total
Jun 3 - Jun 4
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
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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
    $267 nightly
    The price is $302 total per night from May 31 to Jun 1
    $302 total
    May 31 - Jun 1
    Total with taxes and fees
    9.4/10 Exceptional! (271 reviews)
    Vine & Sand

    Vine & Sand

    47100 New York 25 Southold NY
    $415 nightly
    The price is $474 total per night from May 28 to May 29
    $474 total
    May 28 - May 29
    Total with taxes and fees
    9.8/10 Exceptional! (16 reviews)
    The Bentley Hotel Southampton

    The Bentley Hotel Southampton

    161 Hills Station Rd Southampton NY
    $227 nightly
    The price is $259 total per night from May 28 to May 29
    $259 total
    May 28 - May 29
    Total with taxes and fees
    9.6/10 Exceptional! (505 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
213 Cottages
Lowest Price
$187
Highest Price
$696
Popular accommodation
North Fork Resort, 1-bedroom cottage with Grove Beach 🏖️ access., 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Fairy Tale Guest Cottage in Magic Garden by Pool, Cozy & Warm Getaway Cottage in Beach Community, 1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum. , The gardners Cottage 1 mile from long Island Sound - pet friendly, NEW Coastal Cottage 2 Miles to Beach + Lake Access, Beach Cottage, private beach and pass

More to Explore