Wellfleet Vacation Rentals - House & Cottage

Stunning Water Views from ''Windward'' on the Bay

4 BR | 2 BA | Sleeps 8 | Quick View

Key Amenities

Oceanfront
Pet friendly
Rentals by owner

About this property

With amazing water views (some of best on Cape) this wonderfully comfortable house is lovingly furnished (Persian rugs, antiques, authentic cottage furniture, custom made coaches, chairs, day bed,and stuffed rocking chairs) and as such has a unique ambiance. Unlike the typically constructed house, Windward ...

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Property Type

Wellfleet House

"Another Outstanding Stay at Windward"

This is our third consecutive year renting Windward for our extended family. Elisabeth and Doug are extremely thoughtful hosts, ensuring that their guests have everything they need in a beautifully maintained ...

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Waterfront Cape Cod Cottage with private beach 5 bedrooms

5 BR | 2.5 BA | Sleeps 16 | Quick View

Distance to beach: 10 feet to Mayo

$571

avg/night

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Key Amenities

Beachfront
Kid friendly
Oceanfront
Pet friendly
Rentals by owner

About this property

Enjoy one of the Chequessett Inn's original bluff cottage's built in the early 1900's on Mayo Beach by Captain L.D. Baker. This beautiful large waterfront cottage has panoramic views of Wellfleet Harbor stretching all the way across to the Cape Cod National Seashore's Great Island. ...

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Property Type

Wellfleet Cottage

"Quintessential Old Time Cape Home"

One of our daughters was getting married a the Chequessett Club right down the road from this cottage. Stepping into the cottage was like going back to an earlier time period. The knotty pine walls and ...

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Wellfleet - Gull Pond Area!! (MM-871)

4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to Gull Pond

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Key Amenities

Kid friendly

About this property

This beautiful contemporary Cape has all the right ingredients to make your stay a memorable experience. Located just steps away from the Wellfleet woods, there are plenty of trails to walk and Gull Pond is just about 1 mile away. Inside we have a first floor master with full bath. Laundry on the first ...

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Property Type

Wellfleet House

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Summer/Fall/ Winter/Spring Getaway for up to 2 Families.

4 BR | 3 BA | Sleeps 10 | Quick View

$600

avg/night

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About this property

This 3,000 sq ft. plus rental is equipped like a home with quality furniture, appliances, finishes and every amenity you could think of to make your vacation complete. Our home boasts an open floor plan, with 4 bedrooms - one downstairs (queen bed), two upstairs (one with two twin beds and another with ...

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Property Type

Wellfleet House

"We found the house that accomodated our 3 generation family!!!!"

This beautiful home is spacious, wonderfully cared for, conveniently located and private. The layout allowed for 10 of us -3 family units-to have privacy and quiet. Up and downstairs living areas were ...

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Wellfleet Cottage, Central Heat/AC, Enclosed Porch, Wooded View near Duck Pond

2 BR | 1 BA | Sleeps 5 | Quick View

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Key Amenities

Kid friendly
Rentals by owner

About this property

Private end unit in a small cottage community. Two bedrooms (1 double bed, 3 twin beds); pleasant sitting room; kitchen area; porch with table for dining and wooded view. Heating/air conditioning units. Charcoal grill. Comfortable and fully equipped, including dishes, utensils, coffee maker, microwave, ...

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Property Type

Wellfleet Cottage

"Love this place"

I love the homey feel of the cottage, the woods out back, the Wellfleet C of C guide covers hanging on the walls. I'll be staying a week in both June and Sept. this year as I can't get enough of Wellfleet ...

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Lieutenant Island Treehouse Getaway

4 BR | 3 BA | Sleeps 8 | Quick View

$500

avg/night

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Key Amenities

Beachfront
Kid friendly
Oceanfront
Pet friendly

About this property

Set within the trees and surrounded by the neighborhood wildlife, this charming 4 bedroom, 3.5 bath home has everything one would need for the perfect Cape Cod vacation, including stunning sunset views across the Wellfleet Bay and a gorgeous stretch of private beach that is just a minute walk from the ...

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Property Type

Wellfleet House

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Contemporary 3BR Saltbox Nestled in Woods

3 BR | 2 BA | Sleeps 6 | Quick View

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Key Amenities

Rentals by owner

About this property

Chequesette Neck area in private woodland setting. Large wrap-around deck with beautiful sunset views. Near lovely bay beach suitable for families with small children. Convenient to library and town center. Bright, airy, open design with cathedral ceiling. Accented with soothing colors of sand and sea. ...

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Property Type

Wellfleet House

"Sweet, lovely situated saltbox cottage"

This cottage satisfied all our needs. About a mile from the center of Wellfleet. Quick drive to the bay, kettle ponds, and the rail trail for biking. A few other rentals nearby, but felt private and ...

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Walk to Wellfleet Pristine Bay Beaches!

3 BR | 3 BA | Sleeps 10 | Quick View

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Key Amenities

Kid friendly
Rentals by owner

About this property

This upscale home is located in a quiet child-friendly neighborhood and is great for evening strolls to private beaches near Indian Neck and Wellfleet Harbor. End your day watching amazing sunsets or reading a book on the private back deck as you enjoy the warm ocean breeze.You will instantly feel ...

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Property Type

Wellfleet House

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Map

Find a Wellfleet vacation rental for a unique trip

Wellfleet's uniqueness is easy to appreciate in so many ways. It's a quaint town that blends together an eclectic collection of artists, a surprisingly diverse set of dining options, a cute little downtown area, and almost too many outdoor attractions and activities. The fact is, you have to experience it to appreciate it. So, if you're considering booking a Wellfleet vacation rental, don't hesitate. If you're staying somewhere else on the Cape, make sure a day trip (or two) to Wellfleet is on your list.

The town is one of the world's best oyster beds and has had that reputation and industry for decades. Its devotion to shellfishing permeates so many aspects of vacationing in Wellfleet. The restaurants have extremely fresh seafood options, and there are events and community gatherings celebrating the the connection and reliance on ocean fare. Travelers come from all of the world and all over New England to enjoy the Main Street in Wellfleet so don't miss it.

Our vacation rental options range from romantic cottages for a couple to houses for an entire family. Where your rental is located in Wellfleet depends on what you want proximity to, but ultimately most of the town and attractions are quite walkable and/or bikeable. Regardless of location, you'll enjoy the space, comfort and privacy of home, often for less than the cost of booking a hotel room.

Wellfleet, MA travel advice

Many people have heard of Wellfleet oysters and maybe have preconceived notions about the Outer Cape. Here's the deal:

Wellfleet will surprise you. It has diehard, annual visitors who flock to book their Wellfleet rentals from Memorial Day to Labor Day months and months in advance. If you're considering booking something around OysterFest, then you better get going, like now! If you don't end up staying in town, you still should 100% prioritize visiting one or some of its famous summer spots. If forced to choose, we'd recommend a day trip that includes a walk around the galleries on its picturesque Main Street before heading over for some live music and food at the Beachcomber so you can bask in the glory of Cahoon Hollow Beach.

If you're lucky enough to find and book a vacation rental in Wellfleet, be sure to hit at least a handful of the great restaurants, cafes, and outdoor spots that we mention below. But first thing is first, start perusing our great collection of rentals now.

Popular attractions and activities

We don't say this lightly considering just how diverse and beautiful virtually every place on Cape Cod is, but: this Outer Cape town has an amazing array outdoor attractions. It's almost impossible to define all of them so we'll list some starting points here, but feel free to ask us for more advice:

- Marconi Beach: You know that image of a beach with a natural looking panels of wood loosely strung together dancing in the wind and sun over a golden sand beach? Yeah, you're gonna love this beach.
- The Massachusetts Audubon Wellfleet Bay Wildlife Sanctuary: This is a great day trip for families and singles alike featuring a narrow boardwalk and five miles of trails spanning woodlands, beach, and salt marshes. Don't miss the aquarium and educational content if you go.
- Atlantic White Cedar Swamp Trail - Another spot on the CC National Seashore that spirals around through the wods near the Marconi Wireless Station. A can't skip for hikers and naturing loving vacationers.
- Jeremy's Point: If you book a vacation rental here, be sure to rent a boat or hire one to take you out to this remote beach located at the very end of Great Island. Its wildlife and truly remote and pristine shores will wow you.
- White Crest Beach: sand dunes abound this amazing Wellfleet beach on the north side of Marconi Beach. It's less populated than most of the National Seashore beaches -- good for you introverts.
- Uncle Tim's Bridge: if you're staying in a Wellfleet cottage or house near Main Street/town center and want to be in nature in short order, then you can walk over to this boarded walking bridge that jets out over Duck Creek. It's a low-lying bridge built in 1783, originally.

What's the bottom line?

Nature and the outdoors have been a big, big draw for this community and annual summer visitors so you really can't go wrong.

In addition to its natural beauty, there are cultural and historical attractions that travelers staying in a vacation rental in Wellfleet (or nearby) won't want to miss. Its town center and surrounding areas have many art galleries featuring local artists (many of whom are year-round residents). We like the Frying Pan Gallery with paintings and mixed material arts inside and the beach and ice cream across the way. But there are many gallery options walkable from town. Wellfleet Preservation Hall is a beautiful building and will surprise you that it's in such a quaint town. It has open mic every Wednesday and is a popular event spot, too. Keep an eye on the calendar if your cottage rental is in town.

Annual events

The annual Wellfleet OysterFest is put on by Wellfleet SPAT. It's a great celebration and family-oriented festival in the town center. OysterFest is always on a weekend and it celebrates the town's renowned oysters, shell fisherman, culture and traditions. You can buy oysters, look at art, or participate in the silent auction. In our opinion, the most unique and can't-miss part of OysterFest is the "shuck off" where, you guessed it, oysters are shucked in a fun competition. It has been going on for 20 years so add this to your list, for sure.

Perhaps super niche and with not quite so much fanfare, there is an annual Wellfleet Road Race for your runners out there. It usually starts near Mayo Beach and is known to be a gorgeous trek along Wellfleet Harbor.

Ok, maybe this isn't quite an annual event, but big shout to The Beachcomber which has been an institution for 42 years and running! Plus the view atop Cahoon Hollow Beach is regularly cited in national publications and magazines as a country-wide landmark. More below...check it out.

Great restaurants and food in Wellfleet

There are only a few towns on the Cape that can claim to have restaurants and a food scene that is on-par with the some of the best cities and areas in the country. Wellfleet is one of them.

If you're in the mood for a classic and unique beach-side dining and entertainment, check out the Beachcomber. Chances are, you've seen the Beachcomber's bumperstickers on cars and sweatshirts around the Cape. It won't take long for you to see why when you approach the venue which sits on a beach bluff high atop Cahoon Hollow Beach. There's music, a lively bar, and great fried seafood options to go with the view. Singles and partygoers take over around dinner time so be mindful of when you arrive.

The beachcomber isn't the only restaurant on the water that merits mentioning. The west side of the town is where many Wellfleet vacation rental options are and that's also where you'll find Mac's Shack and Mac's On The Pier -- both offer amazing seafood options but with very different dining experiences. Mac's Shack has a bar with a decent social scene (by Cape Cod standards!) so you can get some wild cocktails and even sushi. While Mac's On The Pier in Wellfleet is a super casual "clam shack" directly on Wellfleet Harbor.

To be honest, there are just too many worthy food options in Wellfleet and not enough space! We'd be remiss if we didn't recommend trying Pearl Restaurant for some family-friendly classic seafood, PB Boulangerie Bistro for a fine French dinner and bakery (you can't miss with their bakery!), and the sneaky good, best-kept-secret Flying Fish Cafe, which has some outdoor seating for a great breakfast and brunch experience. We could go on but we're out of space!

Unique Wellfleet vacation rentals on Cape Cod Vacation Rentals

Perhaps like no other place, when you find that perfect, unique rental in the right part of Wellfleet on CapeCodVacationRenals.com, the stars align! We have outstanding options for a one-of-a-kind stay in this haven. Our team can answer any questions you have about your Wellfleet vacation. Find your vacation rental and inquire today!