Holiday rentals in Wellfleet Harbor

4.96 out of 5 average rating, 190 reviews

Flat in Wellfleet

Beautiful Creekside Apartment in Wellfleet Center

Unique romantic apartment overlooking Duck Creek. One large living space which includes kitchen, work area, dining and air conditioned living room with a spectacular view. Queen bedroom and full bath. Small outdoor sitting area with table and chairs to watch the tide role in and out. See the sky change color at sunset and if lucky, catch the moon rise. Access to this private apartment is up a spiral staircase. Close to all of Wellfleet's restaurants, art galleries, town center and the pier.

Superhost

Home in Wellfleet

4.9 out of 5 average rating, 162 reviews

Wellfleet Woods Escape

Open kitchen + living + dining, w/ a wooden pitched ceiling and two sliders overlooking the deck, backyard +marsh. Functional kitchen with Farm sink, DW, cooking and pantry essentials. Two comfortable bedrooms with window AC's, new mattresses, and blackout curtains. Bathroom w/ tub/shower + plenty of towels for beach or house use. Outdoor shower is great in warmer months! Enjoy this quiet, tucked away Wellfleet spot with lots of walking trails and beautiful sunset views just down the road.

Place to stay in Wellfleet

4.97 out of 5 average rating, 237 reviews

Romantic Cape Cod Tiny House + Hot Tub

Welcome to the Romantic Hideaway, our magical, secluded tiny house nestled between lush gardens and the woods alongside our property. Just a short drive to ocean beaches and freshwater ponds, and a pleasant walk to the quaint center of Wellfleet. Wake to birdsong and enjoy fresh muffins on your sunny, private deck. Your stay includes access to our Magnolia Spa with hot tub and sauna (June+); massage is available in July at special guest rates. A sweet, quiet escape on the Outer Cape.

4.9 out of 5 average rating, 165 reviews

Cape Cod Spectacular Waterfront Cottage

Welcome to our internationally acclaimed and regionally featured cottage located on Lieutenant Island in Wellfleet, MA. It's in a private location with panoramic views and a western exposure featuring beautiful sunsets nightly (weather permitting)! TripAdvisor internationally featured property in July, 2015: Bostondotcom in July, 2016: Business Week in July, 2020. Please contact us for nightly, weekly or long term quotes or discounts. Pricing and lengths of stay are subject to change.

4.99 out of 5 average rating, 172 reviews

Home in Wellfleet

Rum Runner’s Shack @ Historic Downtown Wellfleet

Located in Wellfleet Center, enjoy this sublime 528 sq. foot cottage - only 10 minutes from beaches and ponds in any direction. Near Winslow's Tavern, Wellfleet Marketplace, Hatch's, Uncle Tim’s Bridge, Mac's Shack and Wicked Oyster. This 1925 bungalow is the perfect site for a couple or a small family 2 adults/2 children - NOT 4 adults. Linens, ac, cable provided. Parking for ONE vehicle. June - Sept =7 day minimum with Sunday check-in. No pets or 3rd party booking.

4.93 out of 5 average rating, 107 reviews

Tiny home in Wellfleet

Tiny House Living in Wellfleet

Sunny post and beam cottage in the woods of Wellfleet. Easy access to Bay, Ocean and Ponds. Great for a single or couple. Sleeping in loft (steepish stairs and limited head room in loft) full kitchen and bathroom with clawfoot tub and shower and living space downstairs, side door opens to outdoor shower. French doors open to a deck looking out to the woods with a gas grill for cooking out. AVAILABLE WEEKLY- SATURDAY to SATURDAY Massage studio on site

4.99 out of 5 average rating, 169 reviews

Tiny home in Wellfleet

The Huddle Hut—a sweet, neat esCAPE to Wellfleet

The pristine Huddle Hut is nestled in a peaceful, wooded area only a short drive from beaches, restaurants, biking trails and Wellfleet's historic, charming town center. The Huddle Hut is perfect for couples and solo adventurers, only intended for one or two people at anytime: + nestled among trees in a quiet space + standalone building, private deck, outdoor shower + thoughtful, eclectic design + year-round getaway destination

4.92 out of 5 average rating, 184 reviews

Guest suite in Orleans

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

4.99 out of 5 average rating, 213 reviews

Cottage in Eastham

The Salt Pond Cottage

This is a free-standing private cottage that sleeps 2 comfortably. A spiral staircase leads up to a sleeping loft with a NEW QUEEN size Nectar bed! There is a full futon couch on the main level. The kitchen has everything you may need. The most spectacular thing about this home is its close proximity to the National Seashore. The salt pond, bike path, and freshwater ponds are also moments away!

Superhost

Guest suite in Wellfleet

4.71 out of 5 average rating, 24 reviews

Honeybee Haven - 1 bedroom suite w/ private bath

Relax in this cozy ground floor suite in our home on a Cul de sac close to all Wellfleet has to offer. Host Julia, and her friendly pup Doobie, are right upstairs to ensure you have a great experience. Enjoy your own patio, a comfy living room with sofa bed with a new mattress, dining table, kitchenette, private bath with shower, and captive bedroom with queen bed. Sorry no pets.

Superhost

4.88 out of 5 average rating, 105 reviews

Classic Summer Cottage

Stay at a classic summer cottage, in the Wellfleet woods, yet conveniently located a 5 minute drive from downtown Wellfleet. Built in 1938 by 4 women, it still has much of it's original charm. The great room has wood paneling and a cathedral ceiling. This common area has natural wood floors and a fireplace. 2 cozy bedrooms and a small kitchen and bathroom complete the scene.

4.98 out of 5 average rating, 212 reviews

Guest suite in Wellfleet

Charming, private, studio near Gull Pond Wellfleet

Quietly situated 3/4 mile from Gull Pond, 2 miles from ocean beaches, and 1.3 mile from the center of Wellfleet. This is an ideal spot if you are looking for a comfortable base from which to enjoy all that Wellfleet has to offer! Studio apt with microwave, wifi, but PLEASE NOTE: there is no stove and no television.

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Other great holiday rentals in Wellfleet Harbor

Home in Wellfleet

4.91 out of 5 average rating, 22 reviews

2 Bedroom, 5 min walk to bay beach!

PaulaRating, 5 stars3 weeks ago

Stayed here for two nights with an infant and a dog. Appreciates the dog friendliness. Great location, peaceful, near Provincetown. Recommend for two adults and a dog! Big deck outside as well. Easy parking and instructions provided by host. Good for a short term weekend getaway.

Cottage in Truro

5 out of 5 average rating, 3 reviews

Tiny Truro Treehouse

LucindaRating, 5 stars3 days ago

The most charming place! I would definitely come back next time I visit cape cod! Ps, you must go to Salty Market around the corner, thanks to Jennifer’s recommendation!

4.79 out of 5 average rating, 14 reviews

Waterfront Cape Cottage by Wellfleet’s TOP Beaches

BrettRating, 5 stars4 weeks ago

Raquel's place is charming and cozy with lovely views. It's in a community of eight or more other small Cape Cod-style cottages on a small property, though it is the last one in this group, closest to the shore, so significantly more private than others, and the neighbors we met were all very friendly. It's a big walk down a steep hill to use the kayaks, and they can only be used at high tide, so definitely be aware of that if you're planning to go boating. The beds were comfortable and the cottage was tidy. Over all, we had a lovely stay and Raquel was an extremely accommodating host when our dates shifted. All of this made for a nice, affordable, and pleasant location for an off-season trip to the Cape.

5 out of 5 average rating, 6 reviews

Cabin in Wellfleet

Cozy Wellfleet Cabin w/ Lofted Ceilings

JannaRating, 5 stars10 months ago

The Deck2 location is peaceful with a boardwalk around the cottages and the pond. You're right off the highway, but set down in a hollow so with the windows closed (and excellent "split" AC), it's quiet for activities during the day and for sleep at night. It's "tiny house" living in concept, but all the essentials are there--just enough pans and pots and utensils, but if you're a real cook, bring your fave implements and a small saucepan. Nella supplies lots of spices and a little bottle of olive oil. The bath towels were soft and lush. Lots of cleaning supplies and shampoo/cond/shower gel available She also provides a beach umbrella (worked well!) and beach chairs and beach towels (we didn't use those as we bring our own). The deck is nice for sitting in the sun; grill works well. When we asked for a more coffee mugs, she brought some by. There's a nutribullet blender and a large pot for boiling lobster. Toaster works for bagels. Beds are comfy and there are 2 Roku TVs.

5 out of 5 average rating, 14 reviews

“The North Star”- sweet cottage near bayside beach

MaylisRating, 5 stars2 days ago

We had a wonderful stay as a family of 3 with our 4 year old. Though small, we had everything we needed and everything was very clean and comfortable. A 5 min drive to the beach as well as town made everything very easy and enjoyable. Highly recommend and would love to come back.

4.98 out of 5 average rating, 51 reviews

Tiny home in Brewster

Whitecap Cottage-Tiny Luxury! PETok-Fireplace/pit

Ryan & SandraRating, 5 stars1 week ago

Everything was perfect and just as described. We had a wonderful stay and highly recommend! It was very peaceful, near lovely beaches, and well equipped for a romantic getaway. Great communication and loved the electric fireplace!