For the 50+ Traveler
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Soft ocean breezes, brilliantly warm sunshine, white sandy beaches, and a zen vacation vibe that will leave you completely relaxed and rejuvenated: Cape Cod and the Islands have gorgeous vacation rental options on the water, in town, or tucked away in a quiet corner. No matter what your vacation budget restraints are, you are sure to find the perfect beachy vacation rental property to satisfy your toes-in-the-sand adventure cravings.

The writer eating at Sesuit Harbor Cafe.
Sandi Barrett

Bargain

Bargain rental properties may find you more than a few steps from the beach; however, what you save in fees can enhance your discretionary spending. This is a good way to leave some extra coin to search out the best monster lobster roll -- and there are plenty of options to taste test. Your first stop should be the Sesuit Harbor Cafe. Their lobster rolls are amazing. You can munch happily on perfectly cooked lobster while seated at one of their many picnic tables enjoying a relaxed waterfront meal. With that advice in mind, here are my favorite budget rental options.

Oak Bluffs Gingerbread House

Price per night: Starting at $150

Accommodations: Sleeps 4 in 2 bedrooms

Finding a budget-friendly stay on Martha’s Vineyard that is this cute and close to everything is nearly impossible. The Oak Bluffs Gingerbread House operated by a Vrbo Premier Host gives you the security of knowing you’re settling into a well-managed property. Sporting a classic white Cape-style interior punctuated by ocean blues and wooden accents, the house is all about charm and that rustic vacation feel. The cottage is a short walk to the beach, dining, and shopping. This adorable gingerbread house is ideal for a sweet couple’s getaway adventure.

Autocamp Cape Cod

Price per night: Starting at $135

Accommodations: Sleeps 2 adults and 2 children (or 3 adults)

Always wanted to give camping a try, but not ready to hitch a tag-a-long up to your truck? Autocamp Cape Cod has filled the camper rental void by packing their lot full of Airstream Suites (trailers), Luxury Tents (glamping), and Vista X Suites (modern cabins). Camping never felt so good. All this outdoor packed fun is just a five-minute drive to the local beaches. Autocamp offers complimentary mountain bikes to explore the area. This getaway stay is a great way to give camping life a try and is an affordable family vacation.

An exterior view of Cranberry Cottage.
Sandi Barrett

Cranberry Cottages

Price per night: Starting at $128

Accommodations: Studio to three-bedroom options

As soon as you enter the property’s circular drive, you feel a wave of summertime nostalgia wash over you. These perfect, pristine little Cape Cod cottages with gorgeous landscaping, weathered shingles, and bright white trim takes you back to a simpler time. Renting one of these darling houses, the original “tiny house” accommodation, provides a peaceful, relaxing old-time Cape stay. Cranberry Cottages is a collective of individual owners. You can find several of these charming cottages on Vrbo, including this Comfy Cottage that sleeps four. Be sure to visit Premier Host owner Amy’s favorite beach, First Encounter Beach.

Mid-Range

Many mid-range stays can be found on and off the shoreline. From large reunion-style homes to small cozy getaway cottages, the Cape and Islands have your dream beach vacation options covered. For a fun and tasty dining experience, visit Cisco Brewers on Nantucket Island. While tasting one of their classic brews, grab a unique nosh at one of the ubiquitous food trucks offering excellent local eats, and after a night out, rest your head at one of these mid-range Cape Cod (and beyond) stays.

Balcony view of the beach from Panoramic Views.
Sandi Barrett

Panoramic Views

Price per night: Starting at $299

Accommodations: Sleeps 4 in 2 bedrooms

Grab your bike and hop on the ferry from Boston to Provincetown, P-town to the locals. This adorable Panoramic Views on-the-beach apartment is steps from all the fun, crazy vacation getaway activities P-town has to offer. Stop by the neighboring Harbor Lounge or enjoy a cocktail on the deck overlooking the beach; you will love this sweet little apartment. The decor has clean lines and an uncluttered style that lets the views shine through. The panoramic water views from the bedrooms are so spectacular you won’t want to get out of bed. Owned by a Vrbo Premier Host, you can be assured of a quality getaway experience. Note: There is no parking with this stay.

Martha’s Vineyard Oceanview Retreat

Price per night: Starting at $415

Accommodations: Sleeps 5 in 3 bedrooms

Airbnb Superhosts James and Susan are the landlords of Martha’s Vineyard Oceanview Retreat in Aquinnah. Walk to the island’s beautiful beaches and return to your own modern, island-inspired oasis. Sip your favorite cocktail in the living room as you marvel at the panoramic view of the vineyard. The pristine white interior canvas of the property allows the gorgeous views to capture and hold your attention. Feel the workaday cares slip away as you make this classically inspired stay your home away from home.

Dining area at Amazing Family Friendly In-Town.
Sandi Barrett

Amazing Family-Friendly House In Town

Price per night: Starting at $731

Accommodations: Sleeps 12 in 5 bedrooms

This stay is in the perfect location, just steps from all the downtown Chatham action but situated on a byway that feels secluded and quiet. The seats-10 dining room table has enough space for everyone and offers views of the private yard. This charming rental is perfect for a family reunion week. Everyone has access to all the fun without having to pile the gang in a car. As an Airbnb Plus rental offered by a Superhost, you know you are going to love this stay at this cozy Family Friendly In-Town accommodation.

Splurge

There is no shortage of exquisite stays on the Cape and Islands. When money is no object, you can relax with style and a location to suit your needs. Fine dining goes hand in hand with a splurge stay, so make a reservation at Chillingsworth, one of the best restaurants on Cape Cod. Their Dennis and Brewster Oysters on the Halfshell are legendary. If you are in the mood for a lazy type lobster, try the Angel Hair Pasta with Lobster smothered in Lobster Basil Cognac Cream. Yum!

Beautiful Chatham Mansion.
Sandi Barrett

Stunning Chatham Mansion (Walk To Town, Beach, Chatham Bars Inn)

Price per night: Starting at $1,100

Accommodations: Sleeps 12 in 7 bedrooms

A gorgeous Chatham mansion situated in a quiet, central neighborhood within walking distance of downtown Chatham, Chatham Bars Inn, and three beautiful beaches. Take your pick of Lighthouse Beach, Claflin Landing Beach, or Andrew Hardings Beach, they are all a half-mile or less on foot. This cozy property has space for everyone, relax in an Adirondack chair while enjoying the wide sun-soaked deck or curl up with a beachy read on the cozy backyard patio. Grab a towel and head down to the beach to watch the sun set.

Bill is the best Superhost and notes his house “really lends itself nicely for families who love the convenience of being close to the beaches and downtown.” This property has room for the whole family. It is a special multi-generational getaway and is the “perfect escape for a week in the summer or an extended weekend in the fall.”

Where The Sky Meets The Sea

Price per night: Starting at $1,429

Accommodations: Sleeps 10 in 5 bedrooms

Your own private oasis steps from the beach with two wrap-around porches, gorgeous landscaping, an outdoor patio, and room for the entire family. Grab the kids and grandkids for an exceptional beachfront vacation. Step out onto your own section of the beautiful beach and stroll down the shoreline to Mayflower Beach, one of the Cape’s most loved beaches. The casual and well-appointed interior is perfect for an oceanside vacation family reunion. Where The Sky Meets The Sea is a Vrbo Premier Host property ideal for your Cape Cod getaway.

Hilltop Estate

Price per night: Starting at $4,000

Accommodations: Sleeps 8 in 6 bedrooms

This is Island luxury at its finest. Hilltop Estate boasts a saltwater infinity pool, private back yard, and relaxed luxury interior that exudes Cape Cod’s beachy vibe. The accommodations include the main house, a guest house, and a cottage, each with two bedrooms providing ample privacy for large family reunions or group getaways. Centrally located, this property is within a few miles of everything Nantucket Island has to offer. Few of us live in this kind of luxury every day, but you can experience luxe living on your island vacation.

Pro Tips

Visiting Cape Cod and the Islands for a classic beach getaway is the ultimate in a decompression-style vacation. Options for in-town, toes-in-the-sand, and country-style estates are at your fingertips. Visit on the shoulder seasons for the best rates and lovely cool days. Check out The Best 11 Beaches on Cape Cod to help with your beach day selection. For the lighthouse seeker, Cape Cod has some great finds, and 7 Beautiful Lighthouses To Visit On Cape Cod will get you started on the right path.

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