Holiday houses in Wellfleet

4.89 out of 5 average rating, 149 reviews

In the Heart of Wellfleet and Walk to Mayo Beach

Beautifully renovated 1850 Greek revival house. Private apartment is on the second floor with private wide accessible outside stairway. It is a 3-4 room apartment and is perfect for a couple and at most a total of 4 adults. PLEASE NOTE if you are not a couple and do not want to share a bed , you will need to rent the second bedroom at $45 per night per each additional person.The location is perfect in the center of quaint picturesque downtown Wellfleet. Private parking. No children under 8.

Apartment in North Eastham

4.91 out of 5 average rating, 269 reviews

Eastham Escape

Private cozy clean 3 room en suite with private entrance. Entry room has small fridge, stocked coffee bar, microwave, water bubbler, and closet with beach chairs, towels, cooler, and dog water bowl. No full kitchen. Middle room has couch and smart t.v. Bedroom with comfortable queen and full bath. 5 min to 2 National Seashore pet friendly beaches. 5 min to Wiley park with pond and dog walk. 3 min to sunsets at the bay. Walk to bus, bike trail, restaurants. 23 miles to Ptown. Sleeps 1 o2 adults

4.96 out of 5 average rating, 190 reviews

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.

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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, 239 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.

4.95 out of 5 average rating, 240 reviews

Cottage in Eastham

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

4.99 out of 5 average rating, 173 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.

4.98 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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Popular amenities for Wellfleet holiday rentals

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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

4.96 out of 5 average rating, 23 reviews

Guesthouse in Wellfleet

1-Bedroom seasonal cottage near National Seashore

KarlRating, 5 stars5 days ago

My wife and I had a lovely time at Leslie's cabin; great vibes, wonderful outdoor shower, fresh air, and great access to all of the charms of Wellfleet, Truro, and Provincetown.

Cottage in Wellfleet

5 out of 5 average rating, 18 reviews

Walking distance to the Ocean! Cottage Number 1

WhitneyRating, 5 stars9 months ago

Beautiful, quite location on Cape Cod right by the beach. On a private road, with a very short walk and stairs down to the beach. Cottage has everything for a comfortable stay. Wifi was inconsistent and was not suitable for remote work.

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

4.89 out of 5 average rating, 75 reviews

Cottage in Wellfleet

Pine Lodge - spacious and dog friendly!

Taboucher12@Gmail.ComRating, 5 stars5 days ago

What a great place! Super conveniently located, beautiful pond, an incredibly relaxing atmosphere! Will certainly return!

Cottage in Wellfleet

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!

Tiny home in Truro

4.79 out of 5 average rating, 90 reviews

Studio Cottage ~ Queen Bed

LizRating, 5 stars3 weeks ago

The cottage at Prince of Whales was perfect for a weekend getaway. While small, it was beautifully appointed. We weren’t there long enough to utilize the kitchen much, but I was so impressed with how well stocked it was. The bed was comfortable and the heating/cooling unit kept the space nice for the unseasonably cool weather we had. The location was great for a short drive to Provincetown for a daytime adventure, and to Wellfleet. A lovely spot well worth the money!

4.96 out of 5 average rating, 78 reviews

Modern and Bright Wellfleet Studio - Walk to Ponds

JessicaRating, 5 stars9 months ago

Perfect peaceful stay as always, Mary was very helpful and provided extra care with us as my husband had an ankle injury and on crutches. Mary was kind enough to help with my bags and provide accommodations to make the trip easier for us. Clean and bright studio with easy access to all surrounding beaches and ponds.

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