Holiday houses in Wellfleet

4.96 out of 5 average rating, 190 reviews

Apartment 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.

4.97 out of 5 average rating, 190 reviews

Guesthouse in Wellfleet

Abundant Blessings Cottage – Wellfleet

Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.

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

Guest suite in East Orleans

4.92 out of 5 average rating, 184 reviews

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, 212 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

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.

4.89 out of 5 average rating, 183 reviews

Guest suite in Wellfleet

★Exceptional deal in Wellfleet!

Enjoy peace and quiet in our two bedroom suite with private bath and patio. Separate entrance and off street parking in a quiet neighborhood with easy access to restaurants and activities. Walk to popular restaurants and bike rental. Golf, beach walking, bird watching, hiking and more are close by. Walk to town and private kettle pond.

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.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Wellfleet holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Wellfleet's top sights

Marconi Beach25 locals recommend

Cape Cod National Seashore18 locals recommend

Cahoon Hollow Beach14 locals recommend

Other great holiday rentals in Wellfleet

Cottage in North 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!

4.95 out of 5 average rating, 22 reviews

Guesthouse in Wellfleet

1-Bedroom seasonal cottage near National Seashore

PhilippRating, 5 stars1 week ago

we had a great stay in leslies lovely cottage. everything as described; beautiful and calm area, spacious terrace, cozy interior. would come back!

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.

4.99 out of 5 average rating, 69 reviews

Bungalow in Wellfleet

Beach Bungalow - Cape Cod Classic #2

RobinRating, 5 stars1 week ago

We enjoyed every minute of our stay! The bungalow is perfect - well maintained, plenty of space, a well stocked kitchen and comfortable beds. It felt like a true home away from home. Rosemary was incredible - gracious, helpful and very communicative with us. Thank you Rosemary! We hope to be back!

4.98 out of 5 average rating, 45 reviews

Home in Wellfleet

Wellfleet home tucked in 1.5 acres of lush gardens

AlexRating, 5 stars3 weeks ago

Absolutely Wonderful Stay! This place was perfect , the house had everything we needed and more. My 2.5-year-old daughter especially loved the backyard and the abundance of toys. We truly didn’t want to leave and are already looking forward to coming back! Rebecca is an incredible host - warm, responsive, and so helpful. Her local recommendations were better than TripAdvisor, Yelp, and Google combined! We also loved the proximity to Wellfleet and the delicious PB Boulangerie bakery nearby. Highly recommend this stay to anyone visiting the area

4.82 out of 5 average rating, 22 reviews

Apartment in Wellfleet

Peaceful Wellfleet

DianeRating, 5 stars3 weeks ago

What a peaceful and beautiful location! After 4 days of staying in downtown Boston, Tracy's place was just what we needed to decompress. Wellfleet is situated where it was easy to enjoy parts of the Cape Cod National Seashore as well as Provincetown all in one day. Plus due to our 16-day New England trip, we needed to do laundry. Thankfully Tracy's place had a washer, dryer, and laundry detergent! Tracy recommended the Flying Fish for coffee and pastries. She also suggested PJ's for scrumptious clam chowder. Both places were "wins"! We highly recommend a stay at Tracy's!

4.94 out of 5 average rating, 33 reviews

Wellfleet Cottage on the Bay- Waterfront Home 🏖

RebeccaRating, 5 stars10 months ago

I can’t say enough about this amazing cottage beautifully situated on a peaceful beach. The perfect weeklong family getaway and the ultimate place to stay for families with little kids. Definitely plan to make a yearly trip!

Superhost