Plum Island is a small island in the town of Southold in New York. At it’s widest point, Plum Island is only 3 miles long and 1 mile wide, and it serves as home to the Plum Island Animal Disease Center. Access to the island is controlled solely by the Department of Homeland Security, as it is owned by the United States Government. Since Plum Island is located near Long island, there are a variety of beautiful Plum Island vacation rentals for those looking for sandy beaches and peace and quiet.

1. Southold

blue ocean water
Source: Flickr / djmetzger

Located on the north Fork of Long Island, Southold is a small town in Suffolk County. It is home to the Horton Point Lighthouse and Nautical Museum and a variety of wineries and vineyards. Stay at a vacation rental within the town and visit the Southold Historical Society to learn about the history of the region. You can also spend an evening at the Custer institute and Observatory and study the stars and their formations. If you would rather be outdoors, go kayaking and canoeing in the bay or try your skill at stand-up paddleboarding.

2. Cutchogue

wet beach sand
Source: Flickr / HeatherLWilliams

A small hamlet in Southold, Cutchogue offers a variety of wineries and vineyards for touring, such as the Pugliese Vineyards, and several art galleries, including the Alex Ferrone Gallery. Visit the Coffee Pot Cellars tasting room and take a bottle of vino back to your vacation rental. Stop by one of the gift shops in downtown to purchase souvenirs for family and friends. Visit Wickham’s fruit farm and pick your own fresh produce, or hop on a boat to take a dinner cruise.

3. Shelter Island Heights

clouds over the sailboats
Source: Flickr / NilsPix

Developed in 1871, Shelter Island Heights is a national historic district in the town of Shelter Island. Vacation rentals offer excellent views of the Dering Harbor, and there are plenty of restaurants and cafes for fresh fish and New England cuisine. Visit the Mashomack Preserve and watch birds and other wildlife in their natural habitat, or rent a kayak to spend time on the open waters. There’s also a brewery to tour and the Shelter Island Historical Society Haven’s House Museum.

4. Sag Harbor

parked boats at the dock
Source: Flickr / Gail Frederick

Sag Harbor is a small village in Suffolk County to the south-west of Plum Island. Vacation rentals vary from beachfront properties to those in close proximity. Take in a show at the Bay Street Theater, or visit the Sag Harbor Whaling and Historical Museum. You can also sign up for a boat tour of Sag Harbor, or spend time at Havens Beach swimming and seashell collecting.

5. Napeague

Source: Flickr / Vetatur Fumare

Located in East Hampton, Napeague is a small hamlet with plenty of white sand and crystal waters to enjoy. Rent a bike for your vacation rental to spend your days pedaling away on the soft sand. Visit one of the several bars and clubs at night for a glass of wine, or stroll through Amagansett Square, where you can find a selection of gift and specialty stores.

6. Montauk

sunset view at the bay
Source: Flickr / Jordan Confino

Montauk is a charming Long Island hamlet located on the eastern end of the South Shore. There are many summer homes blended in with the vacation rentals in the area, where you can mix in with the locals. Climb to the top of the Montauk Point Lighthouse, or take a leisurely stroll through the Hitler Hills State Park. You can also rent a horse to ride on the beach.

7. Hampton

waves approaching the seashore
Source: Flickr / julianomarp

The Hamptons is an extremely popular summer destination along eastern Long Island’s South Fork. Often known as the playground of the affluent, the Hamptons boasts 18th Century architecture, high-end restaurants, and a variety of boutiques. When choosing a vacation rental in the Hamptons, you can find many different attractions to enjoy. Visit the Long island Aquarium, or stop by the Palmer Vineyards for a tour and wine tasting.

8. Peconic

swimming geese at the river
Source: Flickr / Russ

Peconic is a small Hamlet just south of Southold. Take a vintage tour of the region, then make a stop at the Sannino Bella Vita Vineyard, where you can sample some of the finest blends of the region. Be sure to take a bottle back to your vacation rental with you so you can enjoy the sunset on the water with a glass. Ice cream lovers relish the thought of the Catapano Dairy Farm, where you can watch milk being gathered and learn how they make a variety of products.

9. Orient

lighthouse on an island
Source: Flickr / Harvey Barrison

Orient, New York, is a quiet location for vacation rentals near Plum Island. Take a ride on the Cross Sound ferry, or spend the day in the sun on the Orient South Beach. For the outdoorsman, boat charters take you out in the Atlantic for fishing, or you can stop by one of the local golf clubs for 18 holes before turning in for the night.

10. Greensport

parked boats near the port
Source: longislandhotspot.com

Greenport is a historic fishing port on the North Fork of Long Island. It is well known for its fine restaurants and shopping. Take the kids to ride on the antique carousel located right by the water, or go on a boat tour of the surrounding region. Spend a few hours at the Railroad museum, or stroll through the local farmers market for fresh produce to cook when you return to your vacation rental.