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
$275 nightly
The price is $314 total per night
$314 total
Sep 15 - Sep 16
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, a picnic area, and barbecue grills.
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
$197 nightly
The price is $222 total per night
$222 total
Sep 15 - Sep 16
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

Westbrook CT
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
'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.
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.
Enchanted Waterfront Cottage

Enchanted Waterfront Cottage

Old Lyme CT
Guests staying at this cottage have access to barbecue grills and a garden.
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.
Charming 1920's no frills cottage in peaceful Old Saybrook

Charming 1920's no frills cottage in peaceful Old Saybrook

Old Saybrook CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Waterfront! Brand New Cozy Cottage in Old Lyme, CT

Waterfront! Brand New Cozy Cottage in Old Lyme, CT

Old Lyme CT
At this cottage, guests have access to features like laundry facilities.
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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
    $345 nightly
    The price is $391 total per night from Sep 8 to Sep 9
    $391 total
    Sep 8 - Sep 9
    Total with taxes and fees
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $83 nightly
    The price is $95 total per night from Aug 27 to Aug 28
    $95 total
    Aug 27 - Aug 28
    Total with taxes and fees
    8/10 Very Good! (1,001 reviews)
    Sound View Greenport

    Sound View Greenport

    58775 County Rd 48 Greenport NY
    $322 nightly
    The price is $368 total per night from Sep 15 to Sep 16
    $368 total
    Sep 15 - Sep 16
    Total with taxes and fees
    8.4/10 Very Good! (705 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
$95
Highest Price
$391
Popular accommodation
North Fork Resort, 1-bedroom cottage with Grove Beach 🏖️ access., 2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Fairy Tale Guest Cottage in Magic Garden by Pool, Enchanted Waterfront Cottage, Cozy cottage near downtown Clinton, Marina & Hammonasset Park, Charming 1920's no frills cottage in peaceful Old Saybrook, Waterfront! Brand New Cozy Cottage in Old Lyme, CT

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