Vacation rentals in Southold

4.9 out of 5 average rating, 21 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

4.79 out of 5 average rating, 43 reviews

Home in West Haven

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

4.9 out of 5 average rating, 99 reviews

Guest suite in Branford

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

4.94 out of 5 average rating, 108 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

4.88 out of 5 average rating, 102 reviews

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

5 out of 5 average rating, 11 reviews

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.82 out of 5 average rating, 67 reviews

Home in Hampton Bays

Spacious Hamptons Oasis | Perfect for Families

Escape to our stunning year-round retreat in Hampton Bays' Red Creek area. With over an acre of lush land, our charming residence offers unparalleled serenity and tranquility just minutes from local bay, beaches, and wineries. Ideal for family fun, friend retreats, and exquisite dining in the Hamptons. For off-season activities, explore wineries, animal feeding farms, apple and pumpkin picking, breweries, and more. Book now for your dream getaway!

Guesthouse in Westhampton Beach

5 out of 5 average rating, 3 reviews

Summer retreat cottage in WHB

Lovely guesthouse with private patio. Steps to Main Street and houses of worship. Enjoy walking or biking to the farmer's market, restaurants, marina, and beach. Bright kitchen and comfortable living room with wifi and smart tv. BBQ and outdoor shower for your use (located on the patio of the main house). Beach pass available for stays of 30+days; access to private village beaches before 10am and after 5pm as per village policy.

4.9 out of 5 average rating, 115 reviews

Home in Shelter Island

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Top guest favorite

4.98 out of 5 average rating, 179 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

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What guests are saying

Westshore Luxury

4.92 out of 5 average rating, 25 reviews1 week ago

We loved our few days here. the house and amenities great and exactly as described. We were a family of four travelling from the UK and wanted a few days out of NYC (our main destination) for a change of pace. The property is in a very quiet residential area a minute away from the beautiful beach. It was very quiet in a chilly April but I guess may be quite different in the summer! We house was walkable (about 10/15 mins) from the main strip of shops and restaurants and a quick drive (10-15 mins) to New Haven for lots of other dining options. We enjoyed trips to New haven and Mystic during our visit. Would recommend!

Home in West Haven

What guests are saying

Direct Shoreline Long Island Sound Waterfront

4.95 out of 5 average rating, 80 reviews7 months ago

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

Cottage in Guilford

What guests are saying

Stylish Beach Getaway: pool & walking location

5 out of 5 average rating, 9 reviews6 months ago

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Home in North Fork

What guests are saying

Hop Skip and a Jump to the Beach

4.97 out of 5 average rating, 35 reviews8 months ago

Our first ever stay at 'Hop Skip and Jump' really met all of our expectations and needs for the week of 8/10-8/17/24! I have never in my 70+ years of spending a summer week in Old Lyme been so enveloped with 5 star luxury while at the Beach! I would recommend this rental to any small family or a group of girlfriends! Hop

Cottage in Old Lyme

What guests are saying

Captains Quarters | July avail!

5 out of 5 average rating, 16 reviews1 month ago

This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.

Home in East Hampton

What guests are saying

Private Beach access along the Wine Trail

4.92 out of 5 average rating, 12 reviews1 month ago

I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

Home in North Fork

What guests are saying

East Hampton Luxury Beach House!

4.98 out of 5 average rating, 114 reviews9 months ago

Donald was an excellent host - he was super responsive, checked us into the house himself, and offered tons of recommendations of things to do for the weekend. The house was incredible and our group had so much fun - the pool, hot tub, outside deck and overall space was great. 10/10 stay!

Home in East Hampton

What guests are saying

2 Bedroom Hamptons Waterfront Cottage Rental

5 out of 5 average rating, 21 reviews9 months ago

A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.

Guesthouse in Hampton Bays

What guests are saying

Sunny apt in the treetops of Greenport village

4.7 out of 5 average rating, 10 reviews32 months ago

We loved our stay at Meg’s The house is an older home that is beautifully renovated. Nice older touches on a completely new space. The space was immaculately clean. We loved being close to the hub of town, but not on the Main Street We basically parked our car and didn’t need to drive to get a cup of coffee or for dinner. Check in and out was super easy. Didn’t need to communicate with Meg because everything was in order. She even gave us later check out. Would definitely stay again

Apartment in North Fork

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Popular amenities for Southold vacation rentals

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Gym

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Laptop-friendly workspace

Wifi

Stay near Southold's top sights

North Fork Table & Inn86 locals recommend

Croteaux Vineyards70 locals recommend

Sparkling Pointe Vineyards & Winery64 locals recommend

Bedell Cellars62 locals recommend

Southold Fish Market54 locals recommend

Greenport Harbor Brewery and Restaurant54 locals recommend

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