Find Vacation Rentals in Wellfleet

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Wellfleet Information

Wellfleet is a small town just below the tip of the Cape Cod peninsula in Massachusetts. Bordered by the Atlantic Ocean to the east and the Cape Cod Bay to the west, the picturesque town is filled with seaside charm. Fewer than 3,000 people reside in Wellfleet year-round, but in summer, the Cape Cod town comes to life as a popular vacation destination. Much of Wellfleet’s land is preserved and protected. The Cape Cod National Seashore, instated by President Kennedy, covers more than 60 percent of the land area. Freshwater ponds flourish in Wellfleet, in addition to wildlife sanctuaries and peaceful beaches.

If you happen to visit Wellfleet during October, don’t miss the annual OysterFest. Dine on some of the nation’s best seafood, then walk it off and get to know your surroundings on a Wellfleet walking tour. Enjoy oyster cooking demonstrations as well as a shuck-off competition to get into the spirit of the season! For a healthy dose of small-town charm, visit the Wellfleet Drive-In Theater, the only drive-in on Cape Cod. The Payomet Performing Arts Center features live music and theater as well as a circus, providing entertainment for all ages. Visit the art galleries in town, including the Wellfleet Artisan Market, and take home a piece of art to commemorate your Cape Cod experience. To explore the town’s natural beauty, visit the Wellfleet Bay Wildlife Sanctuary for trails, shoreline views and a wide array of woodlands and wildlife.

Visit neighboring town Chatham, MA to visit a lighthouse, explore the beaches and enjoy natural wildlife at the Monomoy National Wildlife Refuge. You can get to Chatham in about an hour and a half by bus, or drive south on U.S. Route 6 for about 30 minutes to reach the town. Take the Flex bus north to Provincetown (or take a 20-minute drive along Route 6) for a day trip to Provincetown, MA. Provincetown is filled with successful theaters, cabarets and nightclubs, making it a popular spot for Cape Cod’s artist community. The New World monument and other Pilgrim era artifacts are popular with Provincetown tourists. For a longer trip, take the whole family and visit Boston – a two-hour trip from Wellfleet by car. Visit the city’s famous parks, like the Public Garden and Boston Common, or walk along the Freedom Trail for a bit of exercise in the city. Baseball fans will head straight to Fenway Park to catch a game, while those interested in history and science can visit the city’s many public institutions and museums.

Tripping.com offers nearly 5,000 rentals in Wellfleet. Bringing a pet? Check out one of over 800 pet-friendly rental spaces! Wi-Fi is available in about 4,100 of Tripping.com’s rentals in Wellfleet. If you’re looking for a cozier getaway, search Tripping.com’s 1,500 rentals with a fireplace to help make Wellfleet feel just like home. Take an oceanside vacation along Wellfleet Harbor, pick a spot near Sunken Meadow park or rent a cabin on the east side of Wellfleet along the Atlantic Ocean for gorgeous sunrise views. Wherever you choose to stay, rentals can start as low as $30 per night. Keep an eye out for properties marked “Instabook,” which can be booked immediately.

The most popular way to get around Wellfleet is by car, and the busiest road – passing from the north end of town to the southern tip – is U.S. Route 6. Biking is popular throughout Cape Cod, and several trails run through Wellfleet. One of the largest is the Cape Cod Rail Trail, named after the old railways which were razed many years ago. The trail runs 25 miles from Dennis to South Welfleet. The Cape Cod National Seashore features another popular biking trail running alongside the ocean. Helmets are recommended for all bikers and required for those ages 16 and under. There are no airports in Wellfleet. The nearest air service can be found 15 miles north in Provincetown at the tip of Cape Cod. Another small airport in Chatham is a 40-minute drive south of Wellfleet. Busses travel to Hyannis, where you can catch another bus line to Boston’s Logan International Airport.