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Insider Secret: Travel in May for Great Values

May is shoulder season in many popular destinations – the weather is pleasant, the crowds are slim, and rates are lower. Here are some great-value getaways to consider.

Florida Keys: Parrot Key Resort, Florida Keys

Opened in 2008, Parrot Key Resort is one of Key West’s newest properties. Each of the spacious waterfront rooms has a patio, porch, or balcony. There are four pools, tropical gardens, and if you like watersports, you can kayak, paddleboard, and Jet Ski during your stay. The resort is near Mallory Square and other attractions of Old Town. Doubles from $179/night in May (versus from $239/night in April).

Related: Best Affordable Beach Resorts

New England: Ocean Edge Resort, Brewster, Cape Cod

Originally built for one of Brewster’s wealthiest residents, this seaside property has 337 guestrooms. Families can also choose to stay in stand-alone villas on the waterfront or around the Jack Nicklaus golf course. The resort has two year-round indoor pools, three outdoor pools, tennis courts, and access to the Cape Cod Bike Trail. Head to the town of Chatham for shopping or drive 40 minutes to Provincetown at the tip of the Cape. Although May temperatures not quite warm enough for a dip in the ocean, you can enjoy walks on the quiet beach and build sandcastles. Doubles from $119/night at The Villages, and from $175/night at The Mansion in May (versus from $250/night in July).

Caribbean: Hermitage Plantation Inn, Nevis

The airy, pastel gingerbread cottages of this inn are in a tropical garden of a former sugar plantation. Full tea service is served on the Great House veranda every day at 4 p.m.—a nod to the isle’s British heritage. Try the inn’s rum punch; they have their own 350-year-old recipe that’s a closely guarded secret. Doubles from $150/night starting April 15 (versus from $255 in high season).

Colorado Rockies: Sky Hotel, Aspen, CO

At the bottom of Aspen Mountain, Sky Hotel has 90 guest rooms that were recently renovated. The lobby is a cozy gathering place, with log-beam ceilings, high-back upholstered chairs, and a complimentary wine hour from 5 to 6 p.m. every evening. The property has more than one building and some rooms open to the outdoors. Doubles from $129/night in May (versus from $299/night in June/July and from $450/night in winter ski season).

Pacific Northwest: Rosario Resort, Orcas Island, WA

Orcas Island is an ideal Northwest escape for those who love nature, outdoor activities, and cultural attractions. Rosario Resort surrounds guests with the beauty of the San Juan Islands, offering views of East Sound and Cascade Bay. The Bayside Rooms are a short walk from the Moran Mansion and Rosario Marina and feature sliding-glass doors that open onto a patio or balcony with dramatic island views. Activities include kayaking and whale watching on Puget Sound, visiting the local Farmer’s Market, and touring artisans’ studios. Doubles from $119/night April through June (versus from $149/night in July/August).

More From Travel + Leisure:

Best Caribbean Islands for Foodies

America’s Best All-Inclusive Resorts

World’s Coolest Ferris Wheels

America’s Best Places to Eat Like a Local

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