4 Cape Cod Vacation Spots

Cape Cod is a very popular summer destination offering world-class beaches, seafood restaurants, and outdoor living. Stretching 65 miles from the Sagamore Bridge to the tip of Provincetown, there are a variety of areas to consider when booking a vacation rental. I have narrowed it down to four towns you will want to consider when planning a trip to Cape Cod. I choose these because they offer amazing vacation rentals and services or amenities within proximity that can create a true Cape experience.

New Seabury/Mashpee

Conveniently located about 20 minutes from the Bourne Bridge in the village of Mashpee is New Seabury. Enjoy unforgettable ecotours with

Rideaway Adventures around Popponesset Bay & nearby Sandy Neck in Sandwich. Shop, dine or even get some work done at Mashpee Commons & Popponesset Marketplace. New Seabury is also located about 14 miles from Woods Hole for walking tours of the world-renowned Oceanographic Institute, as well as day trips to Martha Vineyard. The Upper Cape is also home to a number of popular breweries and even a small vineyard! I typically recommend this affluent area for generational trips (grandparents, parents, grandkids) because it's relatively quiet with great golf courses and has a ton of outdoor activities for kids. There are approximately 365 rentals with weekly rental rates averaging around $7,400*. New Seabury is also a popular destination for corporate retreats due to the high-end amenities nearby and the proximity to the Bridges.

Dennis Port

This Mid Cape village is the most affordable and family-friendly destination on this list. Dennis Port is very walkable with many bars and restaurants scattered throughout the neighborhood. Cleat and Anchor is a year-round favorite with live entertainment and one of the most eclectic beer lists on the Cape. You also have to endure the line for ice cream at Sundae School, it's the BEST on the Cape. The Freedom Ferry, a 10 minutes drive down Route 28, offers boat service to Nantucket with FREE PARKING for same-day trips. You could spend the day on the island and be back in time for dinner reservations at the highly recommended Ocean House Restaurant on Old Wharf Road. Attractions include Mini Golf courses, Cape Cod Inflatable Park, Red Wilson Field (Home of the Y-D Red Sox), even an interactive Pirate Museum! Drive to the Northside of Dennis to spend the day at Mayflower Beach. The Northside beach experience is much different than the south side due to the calm water and very low tides, making it an ideal location for young kids. Make sure to grab lobster rolls at the Instagram-famous Sesuit Harbor Cafe, a bucket list Cape Cod experience.

"Dport" has around 675 rental units in the area with the average weekly summer rental fee around $5,400* but you can find 1 or 2 bedroom cottages not too far from the ocean starting around $1,800/week.


The Lower Cape, in general, is a perfect location to choose if you have never been to Cape Cod and want to explore. Chatham is at the elbow of the Cape about an hour (with no traffic) to Provincetown and an hour fifteen minutes to Falmouth. I design many day trips that start in Chatham and follow along either Route 6A to the north or Route 6 in the Outer Cape. People travel to Chatham because of the beaches and amazing outdoor life. Take a Friday night Oyster Farm Tour with Chatham Shellfish Co, a SUP Sunset Glow Tour, or wake up early and catch the sunrise at Lighthouse Beach. Main Street Chatham is a popular high-end shopping district featuring White Marlie, Fisherman's Daughter, and the 100-year-old Puritan Clothing. Chatham also has a thriving restaurant scene with Chatham Wine Bar, Del Mar Bistro, and The Squire and many more. This small area is also home to TWO world-famous resorts, Chatham Bars Inn and Wequassett. Both offer five-star restaurants, Spa services, and awesome waterfront bars.

Chatham is home to around 465 rental units with an average weekly rental fee of $9,400. By far the most expensive vacation destination in the area for very good reason.


This shellfisherman community is about an hour from the Sagamore bridge on the forearm of the Cape between Chatham and Provincetown. Guests that stay on the Outer Cape are usually yearly guests that specifically avoid the hustle & bustle of Route 28 and opt for a serene coastal beach environment. Wellfleet is probably best known for its biggest export, The Wellfleet Oyster. Downtown Wellfleet has fantastic restaurants like The Bookstore, Mac's Shack, and Winslow's Tavern. Day Trips north to Truro or Provincetown offer wine and Distillery tours, unique whale watch excursions, Dune Tours, and eclectic shopping. Check out our blog from last year describing additional itinerary options around Wellfleet.

There are around 500 rentals in Wellfleet with an average weekly rate of $6,800*. There are older cottages available as a more affordable option but they are hard to find and are usually booked directly through the owner.

*Info from airdna.com

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