10 Best May Vacations

The best thing about the month of May is that the weather is nice almost anywhere in the Northern Hemisphere! With that in mind, here is a list of the 10 best May vacations you can take if your vacation plans have you taking off in spring. Vacation rentals are abundant in each one, so you'll have plenty of options to choose from.


Spring hits southern New England in a special way – unlike anywhere else in the world. The area’s harsh winters give way suddenly to a lively green season whose beauty is matched only by the area’s famously stunning autumn. A drive up Interstate 95 will take you past the big, beautiful, century-old houses owned by the well-to-do of Greenwich, up to the urban pulse of New Haven, home of Yale University and some of the best pizza on Earth.

los angeles may vacationLos Angeles

Los Angeles is a must on anyone's list of the 10 best May vacations. There are so many places to go and things to see in Los Angeles, you would need all of May just to dent it. Though L.A.'s beautiful climate and people get most of the publicity, most folks don't realize it has one of the country's best beaches ( Hermosa Beach ), one of its accoustically-best music venues ( Walt Disney Concert Hall ), and one its best museums ( the Getty Center , where you will also find arguably the best view from a museum in the world). And with one of the planet's most ethnically diverse populations, the diversity and excellence of the cuisine is unmatched. For sports fans, nothing beats a gorgeous afternoon at Dodger Stadium or an evening rubbing shoulders with Jack Nicholson at a Laker game.


One of the very first truly great American cities and the “cradle of American liberty,” Boston is incredibly rich in history. Like much of New England, spring is one of the best times of year to visit. After a day full of American history, you can spend the evening in a living monument to baseball history watching a Red Sox game in Fenway Park . While you're in town, be sure to enjoy some lobster from just up the coast in Maine as well as some of Boston's famous clam chowder.


No list of the 10 best May vacations would be complete without a Florida metropolis. Miami is simply the biggest, most diverse, most exciting city in the American Southeast. The beaches are beautiful, the population is gorgeous and the nightlife is hopping.


London's cold winters absolutely erupt into an explosion of green and color in spring. Hyde Park buzzes with people as everyone wants to be outside. The weather is perfect for  walking neighborhoods like Notting Hill , taking a boat ride on the Thames, or visiting the iconic landmarks of one of the world's most historical cities.

Hollywood, California

If you’re a film buff, Hollywood is a must. You’ll want to check out the Walk of Fame on Hollywood Boulevard or stop by Mann's Chinese Theater .  If you’re in town long enough, take in a concert at the Hollywood Bowl, a legendary amphitheater. When travelers list their favorite places to visit, Hollywood is always one of the 10 best. May vacations always be this easy to plan!


Continuing the theme of getaways that beat early summer May heat, there is Chicago. Though during winter Chicago is one of the coldest places in the continental US, in springtime it's one of the coolest. Walk along Lake Michigan , or visit the Sears Tower, the tallest building in the United States. Don't leave town without having an Italian beef sandwich and some of Chicago's famous pizza.

San Francisco

If the idea of going somewhere cool in May appeals to you, you should consider San Francisco. Mark Twain supposedly once said, “The coldest winter I ever spent was a summer in San Francisco.” That means the weather in May is just right. Get some great dim sum in Chinatown , walk around Fisherman's Wharf , or take a tour of Alcatraz .

Tampa, Florida

The Tampa Bay area includes Clearwater and St. Petersburg, and it’s a great place for a baseball fan—in the early spring, before the season starts, the Yankees train there, and by May you can catch a Tampa Bay Rays' home game.

New York City

The lyrics to the old jazz standard “How About You” say, “I like New York in June…,” but May is wonderful. Summertime weather in New York City can be humid, but in May the weather is perfect. It just begs you to stroll through Central Park . Since many kids are still in school in May, New York's renowned museums are less crowded. If you're a sports fan, be sure to visit Yankee Stadium or Madison Square Garden – or both.


Share This


Connecticut Rentals Near the Ocean

Close to Shoreline, Town Green. MidWeek Specials Available. Pets ok, credit card

If this home is reserved, Please call me, I do have other houses. 'We had a wonderful time at this lovely home in Guilford. We found the home to be cozy, comfortable and beautifully decorated. We will definitely stay here again in the future. We ...

AUG 2-9, Spectacular Waterfront Home,Sandy Beach,Hot Tub, Panoramic views

Spectacular Panoramic ocean views from every room in the house; Summer living at it's finest. This Waterfront home is a piece of paradise, located in the Prestigious area of Pawson Park Branford on a Private Road. The perfect beach home for your f...

Sunny 6 BR 1910 Beach House, Dogs OK, Casinos, Private Beach, Fenced Backyard

Sunny and Charming 6 bedroom 1910 colonial is 4 houses away from Private Beach with newer kitchen, 2.5 baths , hardwood floors, stone fireplace, 1st floor washer and dryer, oil heat, new windows on 1st two floors, and private beach right on Long I...

'Captain's Cottage'- Premium Beach House in Crescent Beach

Captain's Cottage was built along with rest of the neighborhood in the 1890's by the Crescent Beach Land Company as a summer get away. Since then the cottage has been extensively remodeled and winterized as a year round residence. It now features ...

Private Waterfront House Located On Connecticut's Premier Beach Resort

Marvel at the beautiful vistas offered by The Beach House at Water's Edge Resort and Spa. Along with these fantastic views, comes spacious accommodations for up to 8 people.There are 3 Bedrooms, 4 Bathrooms, a Bonus Room with Sleeper Sofa, Sun Roo...

Vacation Home Search

Find the perfect rental for your vacation

Join Our Newsletter

Get the latest updates in your email