Vacation rentals in Wellfleet

4.89 out of 5 average rating, 149 reviews

A charming exterior view of a Greek Revival house is presented, featuring a welcoming entrance with black shutters and a large bay window. Colorful flower beds with yellow blooms add vibrancy to the lush greenery surrounding the property, complemented by decorative flags and a cheerful atmosphere.

Apartment in Wellfleet

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.

4.96 out of 5 average rating, 190 reviews

A spiral staircase leads from a wooden deck to a private entrance. A potted plant with yellow flowers sits beside the doorway, complementing the sleek glass doors that provide access to the apartment.

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

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

An inviting entryway is showcased, featuring a warmly decorated door and charming wooden accents. A blue chair sits beside a small table, complemented by a vibrant area rug. Surrounding plants add a touch of greenery, enhancing the welcoming atmosphere of the tiny house retreat.

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

An expansive view of the ocean showcases gentle waves and a clear sky. Two humpback whales are visible near the surface, creating ripples in the water. Light reflections shimmer across the sea, enhancing the serene atmosphere.

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.

4.9 out of 5 average rating, 165 reviews

The living area features an open design with exposed beams and large windows, offering views of Cape Cod Bay. A light-colored sofa and armchair with green accents are arranged around a small coffee table. A woven basket adds texture, while a television and bookshelf are positioned on the wall.

Cottage in Wellfleet

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.

4.95 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.

A charming porch is visible, featuring light blue ceiling boards. The space is furnished with a small white table and two blue chairs, along with a cushioned sofa and an accent table. Natural greenery can be seen in the background, enhancing the serene environment.

4.99 out of 5 average rating, 173 reviews

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

A charming cottage features a sloped roof and large windows, surrounded by lush greenery. A raised wooden deck provides access to outdoor seating beneath a vibrant umbrella. Potted plants and flowers enhance the natural setting, inviting guests to enjoy the peaceful outdoor space.

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

A private outdoor space is surrounded by tall trees, featuring a stone patio with four wooden chairs arranged around a fire pit. A gravel path leads to a cozy seating area with a single chair, alongside a flower pot adding a touch of color.

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

A wooden sign reading 'Snowtop Guests' is displayed among greenery, with soft lighting enhancing its visibility. The sign is positioned near a stone pathway leading to a grassy area, inviting guests to approach the entrance. Lush plants surround the scene, providing a natural ambiance.

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

A serene beach scene captures gentle waves lapping at the shore, leaving behind subtle footprints in the sand. Sand dunes rise in the background, while expansive clouds drift across a clear blue sky, creating a peaceful coastal atmosphere.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

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A space thats all yours, with room for everyone

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Popular amenities for Wellfleet vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Wellfleet's top sights

Marconi Beach25 locals recommend

Cape Cod National Seashore18 locals recommend

Cahoon Hollow Beach14 locals recommend

Other great vacation rentals in Wellfleet

A screened-in porch features two wooden chairs positioned on a brick pathway. A small potted plant is visible near the entrance, and a colorful mat adds a welcoming touch. The surrounding area is shaded by greenery, providing a sense of privacy and tranquility.

Cottage in Truro

4.83 out of 5 average rating, 6 reviews

Tiny Truro Treehouse

HeatherRating, 5 stars5 days ago

Jennifer’s place is so cute and cozy. It was perfect for my solo stay while visiting friends for the weekend. Salty Market is a quick walk down the road for breakfast, coffee and basic staples for the kitchen. I slept very well in the loft bed and I loved the fresh air from the skylight window just overhead. I would happily stay here again on my next visit!

4.96 out of 5 average rating, 23 reviews

The exterior of the rustic dwelling showcases weathered wooden siding and a spacious stone patio. A circular dining table with teal chairs is positioned near a grill. Large sliding glass doors provide access to the interior, framed by trees and natural landscaping.

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.

Superhost

The photo captures a collection of charming coastal cottages nestled along a sandy beach. A road runs parallel to the shoreline, lined with greenery and flowering plants. The sunny sky and natural landscape enhance the serene seaside setting.

4.8 out of 5 average rating, 5 reviews

Sandy beach cottage on Wellfleet Bay

PatriciaRating, 5 stars8 months ago

The stay was everything expected and then some. The beach was amazing and convenient. The house was what was promised and then some.

Superhost

A half bath is presented within the space, featuring warm wooden paneling. A white toilet and a small sink are included, alongside a window that provides natural light. Two glass cups rest on a small ledge, adding a touch of functionality.

Guest suite in Wellfleet

4.59 out of 5 average rating, 419 reviews

Village of Wellfleet

SusanRating, 5 stars2 weeks ago

Andrea’s place was a charming little suite of rooms tucked into a hillside. It was quiet and comfortable and very conveniently located to the Truro center for the arts.

A comfortable living area features a soft grey sofa facing a simple black coffee table. A decorative mantle holds a wooden whale sculpture. Natural light floods in from the surrounding windows, illuminating the space, which connects to a dining area with a table and chairs.

4.98 out of 5 average rating, 45 reviews

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

A serene koi pond is surrounded by natural stone, with water lilies floating on the surface. A small waterfall creates a gentle flow of water, enhancing the tranquil environment. Green foliage frames the scene, providing a lush backdrop.

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!