Southold vacation rentals
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Top-rated vacation rentals in Southold
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Cottage in Riverhead
4.98 out of 5 average rating, 126 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.
Mar 24 – 31
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat
May 12 – 19
Apartment in Southold
4.96 out of 5 average rating, 100 reviewsBright, Southold Studio Apt near beach & town
Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!
Sep 21 – 28
Vacation rentals for every style
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Popular amenities for Southold vacation rentals
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Other great vacation rentals in Southold
Home in Southold
5.0 out of 5 average rating, 14 reviewsLe Petit Cottage Southold NY
Dec 8 – 15
Guesthouse in Southold
4.95 out of 5 average rating, 39 reviewsSouthold- Adorable 1 Bedroom Cottage
Apr 6 – 13
Home in Southold
5.0 out of 5 average rating, 17 reviewsHorton House
Nov 17 – 24
Cottage in Southold
4.94 out of 5 average rating, 32 reviewsBordeaux meets Côte d’Azur—1763 Historic Farmhouse
Sep 5 – 12
Cottage in Southold
4.95 out of 5 average rating, 21 reviewsAdorable Cottage
Dec 11 – 18
Home in Cutchogue
4.96 out of 5 average rating, 72 reviewsSecluded Farmhouse - Studio Apartment Style Unit
Aug 30 – Sep 6
Guest suite in Cutchogue
4.9 out of 5 average rating, 83 reviewsEnjoy a relaxing getaway to the North Fork
Sep 18 – 25
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
Apr 25 – May 2
Home in Southold
4.94 out of 5 average rating, 18 reviewsNEW LISTING: COMPLETELY RENOVATED 4-BED, 3-BATH
Apr 2 – 9
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house ~ Fireplace ~ North Fork Wineries
May 28 – Jun 4
Home in Greenport
5.0 out of 5 average rating, 32 reviewsBeachfront Greenport Villa
Jan 21 – 28
Home in Southold
4.96 out of 5 average rating, 26 reviewsBright Oasis in Beautiful North Fork Wine Country
Mar 11 – 18
Other great vacation rentals in Southold
Cottage in Southold
4.89 out of 5 average rating, 18 reviewsQuaint Cottage Close to LI Sound
Sep 19 – 26
Home in Southold
5.0 out of 5 average rating, 32 reviewsSouthold Comfort - North Fork Getaway
Jul 9 – 16
Loft in Southold
5.0 out of 5 average rating, 11 reviewsEntire Loft-Walk to Town, Beach, Train, Wine Trail
Mar 12 – 19
Home in Southold
4.89 out of 5 average rating, 19 reviewsDockside Getaway in Southold NY
Dec 2 – 9
Home in Cutchogue
4.96 out of 5 average rating, 24 reviewsNorth Fork Estate in Midst of Vinyard
May 1 – 8
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
Nov 11 – 18
Home in Southold
4.97 out of 5 average rating, 35 reviewsWater & Vineyard views, 4 bedrooms
Nov 9 – 16
Home in Peconic
5.0 out of 5 average rating, 11 reviewsCoastal Cottage on the Water
Apr 19 – 26
Apartment in Greenport
4.78 out of 5 average rating, 46 reviews2 Bedroom Greenport Waterfront Coastal Cottage
Dec 23 – 30
Home in Greenport
4.96 out of 5 average rating, 24 reviewsWater front 3 bedrooms 2 bathrooms beach house
Oct 19 – 26
Home in Greenport
5.0 out of 5 average rating, 29 reviewsHistoric Stunner in Heart of Village
May 13 – 20
Home in Cutchogue
5.0 out of 5 average rating, 17 reviewsNorth Fork Escape Heated Pool Beach & Wineries
Apr 7 – 14
Quick stats about vacation rentals in Southold
Total rentals | 210 properties |
---|---|
Rentals with a pool | 60 properties have a pool |
Pet-friendly rentals | 80 properties allow pets |
Family-friendly rentals | 180 properties are a good fit for families |
Total number of reviews | 2.7K reviews |
Nightly prices starting at | $90 before taxes and fees |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Southold?
Four-legged friends are welcome in Southold. Choose from more than 80 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Southold?
Experience the best of Southold with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Southold house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Southold, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Southold have a bbq area?
Absolutely! We offer over 90 house rentals with a bbq area in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have self check-in?
Absolutely! We offer over 50 house rentals with self check-in in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have wifi?
Absolutely! We offer over 160 house rentals with wifi in Southold. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southold have a gym?
Absolutely! We offer over 20 house rentals with a gym in Southold. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Southold?
Southold has more than 160 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Southold?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with self check-in, over 160 homes with wifi, over 90 homes with a bbq area, over 20 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Southold?
Yes! Work meets play with ease at over 110 vacation rentals in Southold featuring dedicated workspaces. Stay connected and productive in your home away from home.
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