
Vacation rentals in Southold
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Top-rated vacation rentals in Southold
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Popular amenities for Southold vacation rentals
Other great vacation rentals in Southold
Top guest favourite

Home in North Fork
4.99 out of 5 average rating, 99 reviewsBeach House in L.I. Wine Country
Guest favourite

Home in North Fork
4.97 out of 5 average rating, 34 reviewsCorwin House
Superhost

Home in North Fork
4.81 out of 5 average rating, 94 reviewsSummer Retreat at the beach , enjoy Wine Country
Guest favourite

Home in North Fork
4.88 out of 5 average rating, 17 reviewsCharming Farmhouse with Pool, Yard, and Walkable
Top guest favourite

Home in North Fork
5 out of 5 average rating, 20 reviewsOak Street Cottage
Guest favourite

Apartment in North Fork
4.96 out of 5 average rating, 97 reviewsLovely 2-bedroom apartment in a historic home
Guest favourite

Home in North Fork
4.93 out of 5 average rating, 54 reviewsLe Petit Cottage, Southold, NY
Superhost

Home in North Fork
4.81 out of 5 average rating, 42 reviewsSouthold Sea'renity
Quick stats about vacation rentals in Southold
Total rentals
260 properties
Nightly prices starting at
$123 CAD before taxes and fees
Total number of reviews
5.4K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
90 properties have a pool
Destinations to explore
- The Hamptons Vacation rentals
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- Rentals with pools Southold
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- Beach
- Charlestown Beach
- Fairfield Beach
- Yale University
- Southampton Beach
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Ocean Beach Park
- Napeague Beach
- TPC River Highlands
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Blue Shutters Beach
- Sunken Meadow State Park
- Amagansett Beach
- Ninigret Beach
- Silver Sands Beach
- Sandy Beach
- Brownstone Adventure Sports Park
- Groton Long Point Main Beach
- Cedar Beach
- Seaside Beach