Southold Luxury Vacation Rentals
Bright Oasis In Beautiful North Fork Wine Country
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
Bright Oasis In Beautiful North Fork Wine Country
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
Bright Oasis In Beautiful North Fork Wine Country
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Beach access
Southold Cottage W/ Patio & Grill - Walk To Beach!
- Cookware/ Kitchen utensils
- Free parking
- Terrace
- Patio
Southold Cottage W/ Patio & Grill - Walk To Beach!
- Cookware/ Kitchen utensils
- Free parking
- Terrace
- Patio
Southold Cottage W/ Patio & Grill - Walk To Beach!
Nf Wine Country Retreat With Dock
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Garden area
Nf Wine Country Retreat With Dock
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Garden area
Nf Wine Country Retreat With Dock
Cheap Southold Vacation Rentals
-
Top location
-
Beach access
Waterfront Home On Goose Creek Dock & Kayaks
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
Waterfront Home On Goose Creek Dock & Kayaks
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
Waterfront Home On Goose Creek Dock & Kayaks
-
Great deal
-
Beach access
Cedar-Shake Cottage, Heated Pool And Gardens
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Outdoor swimming pool
Cedar-Shake Cottage, Heated Pool And Gardens
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Outdoor swimming pool
Cedar-Shake Cottage, Heated Pool And Gardens
Family & Dog-Friendly Getaway!
- Free parking
- Air conditioning
- Flat-screen TV
- Terrace
Family & Dog-Friendly Getaway!
- Free parking
- Air conditioning
- Flat-screen TV
- Terrace
Family & Dog-Friendly Getaway!
Pet Friendly Vacation Rentals Southold
-
Best-rated
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic
- Shared kitchen
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tea and coffee facilities
- Heating
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic
- Shared kitchen
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tea and coffee facilities
- Heating
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic
Fancy Studio Private Entrance
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
Fancy Studio Private Entrance
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
Fancy Studio Private Entrance
Riverside Retreat-Waterfront Walkout Apartment
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Riverside Retreat-Waterfront Walkout Apartment
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Riverside Retreat-Waterfront Walkout Apartment
Southold Vacation Rentals Oceanfront
Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sauna
- Saltwater pool
Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sauna
- Saltwater pool
Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools
Downtown New Haven, Spacious Stay By Yale - Ao Destinations
-
Car park
Charges may apply
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
Downtown New Haven, Spacious Stay By Yale - Ao Destinations
-
Car park
Charges may apply
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
Downtown New Haven, Spacious Stay By Yale - Ao Destinations
-
Beach access
The Pines Men-Only Stay
- VIP check-in/ -out
- Air conditioning
- Fitness centre
- Saltwater pool
- Heated swimming pool
- Outdoor swimming pool
The Pines Men-Only Stay
- VIP check-in/ -out
- Air conditioning
- Fitness centre
- Saltwater pool
- Heated swimming pool
- Outdoor swimming pool
The Pines Men-Only Stay
Southold Vacation Rentals with Private Pool
Villa Signor
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Steam room
- Outdoor swimming pool
Villa Signor
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Steam room
- Outdoor swimming pool
Villa Signor
-
Guest favorite
-
Private beach
The Cliffside Resort Condominiums
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Laundry
- Outdoor swimming pool
The Cliffside Resort Condominiums
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Laundry
- Outdoor swimming pool
The Cliffside Resort Condominiums
Private Apt King Suite, L.I, Ny-Hamptons To Nyc
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
Private Apt King Suite, L.I, Ny-Hamptons To Nyc
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
Private Apt King Suite, L.I, Ny-Hamptons To Nyc
Historic Peaceful Apartment
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Skiing
- Garden area
Historic Peaceful Apartment
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Skiing
- Garden area
Historic Peaceful Apartment
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Private beach
Cozy Garden Apartment Along The Shoreline
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun loungers
Cozy Garden Apartment Along The Shoreline
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun loungers
Cozy Garden Apartment Along The Shoreline
Private Apartment In Southbury 101
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Private Apartment In Southbury 101
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Private Apartment In Southbury 101
Are you in a hurry?
Here is a quick list of Vacation Rentals in Southold, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Bright Oasis In Beautiful North Fork Wine Country |
10.0 / 10 (1 Reviews) |
From 1235$ | |
| King-Bed Room With Private Bath -Free Wifi-- New London-Mystic |
9.6 / 10 (115 Reviews) |
From 140$ | |
| Fancy Studio Private Entrance |
9.3 / 10 (72 Reviews) |
From 105$ | |
| Riverside Retreat-Waterfront Walkout Apartment |
9.5 / 10 (82 Reviews) |
From 286$ | |
| Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools |
9.4 / 10 (63 Reviews) |
From 138$ |
Frequently Asked Questions
What Southold vacation rentals have balconies and great views?
The Riverside Retreat and the Waterfront Home on Goose Creek offer stunning water views and balconies perfect for relaxation. These spaces enhance your stay with beautiful scenery.
Book rooms at Riverside Retreat for sunset views, especially in the summer, to enjoy vibrant colors in the sky.
Which vacation rentals in Southold are dog-friendly?
Family & Dog-Friendly Getaway and Cozy Garden Apartment welcome pets. These rentals provide a comfortable environment for you and your furry friend.
Check their pet policy before booking, and plan to walk your dog along nearby beaches for a fun outing.
What vacation rentals in Southold are suitable for families?
The Southold Cottage and Cedar-Shake Cottage have family-friendly spaces with amenities to accommodate children. They offer plenty of outdoor space for activities.
Opt for rentals with outdoor grills for family barbecues, especially in warmer months when you can enjoy meals outside.
Are there vacation rentals in Southold with swimming pools?
The Cedar-Shake Cottage features a heated pool, providing a perfect spot for family fun. Enjoy swimming any time during your stay.
Visit the pool area early in the morning for a more peaceful swim before other guests arrive.
Which vacation rentals have a jacuzzi or hot tub in Southold?
Luxury Villa: Mohegan Retreat offers a jacuzzi for a relaxing experience after a day of exploring. It's a great way to unwind.
Plan your jacuzzi time for evenings; it's a wonderful way to end your day under the stars.
Where can I find vacation rentals in Southold near the beach?
The Southold Cottage and Riverside Retreat are close to several beaches, making them perfect for beach days. They provide easy access for sand and sun.
Pack beach gear the night before so you can get an early start, especially on weekends when beaches fill up quickly.
Which Southold vacation rentals are best for a romantic getaway?
Villa Signor and the Riverside Retreat provide quiet and cozy spaces ideal for couples. Enjoy private patios and beautiful surroundings.
Consider booking during the off-peak season in fall to enjoy a quieter stay and more intimate ambiance.
How can I plan a perfect vacation in Southold?
Research the local wineries and beaches as Southold is part of Long Island's Wine Country. Make a list of must-see places like the Southold Historical Society and nearby parks.
It's best to visit during late spring or early fall for mild weather and fewer crowds, allowing you to enjoy local events comfortably.
What unique events happen in Southold throughout the year?
During the summer, the Southold Fishers and Farmers Market offers local produce and crafts. In fall, join the Harvest Festival at nearby wineries for food and wine tasting.
Plan to arrive early for market events to secure the freshest produce and avoid long lines.
What are the best dining options in Southold?
Explore local options like The Frisky Oyster and Southold Fish Market for fresh seafood and local flavors. These spots are popular for both dining in and takeout.
Visit these restaurants on weekdays for a more relaxed experience and to avoid weekend rushes, especially during peak seasons.