Top 10 Vacation Rentals In Wellfleet, Massachusetts - Updated 2024

Reyanne Louisse
Reyanne Louisse  
Updated
| 5 min read

If you’re looking for a chance to relax and recharge, head to Wellfleet, a charming town on the peninsula of Cape Cod. Besides its coastal beauty, numerous activities await so that you can have fun while enjoying the peaceful vibe of the town. It is bordered by Atlantic Ocean on the east and Cape Cod Bay on the west. Hence, there is no shortage of spectacular beaches in town. Spend hours swimming and sunbathing on Newcomb Hollow Beach or White Crest Beach. You can even try fishing in the bay. If you’re feeling hungry, make sure to try their famous oysters. Explore more of Wellfleet by going to quaint art galleries, bookstores, and flea markets. Looking forward to visiting Wellfleet? Make sure to stay at one of these homey vacation rentals in Wellfleet, Massachusetts.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.

1. Victorian Dream (from USD 253)

Feel a little regal in this vintage vacation rental! This house offers guests a Victorian ambiance, in sync with the historic charm of Wellfleet. The property comes with three bedrooms that can sleep seven guests, one bathroom, and a half bath with laundry facilities. There are also various corners around the house for you to enjoy a quiet time with a book and a cup of coffee, be it by the fireplace or on the patio. The property’s a short walk from the beach. So, you can enjoy the feeling of sand under your toes anytime.

Aside from its wonderful decor, your stay at this house will be extra safe since the house is equipped with a fire extinguisher, as well as smoke and carbon monoxide detectors. Linens and bath towels are also provided to ensure a comfortable stay.

Stayed at this property?
Wellfleet, Massachusetts, United States
PRIVATE VACATION HOME 7 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Cleanliness:
house is clean and well-maintained
the house was cozy and clean
Host:
management was super attentive
weather was perfect house was very accommodating
Location:
such a cute house in a great location so close to the water
location is very convenient to wellfleet attractions and restaurants
apart from this the house is in a great location and is very quaint
Read more reviews
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2. Woodlands Escape (from USD 225)

Woodlands Escape is a homey property in the northern part of Wellfleet. The house features a loft, two bedrooms, and a basement specifically for kids to sleep and play in.

Aside from its comfy bedrooms, well-equipped kitchen, spacious outdoors, and internet connection, what’s fascinating about this rental is that you get to support local art by booking it. The house is adorned with the previous owner’s artworks which she crafts in a separate studio on the property. Surely, you will get to know Wellfleet a little more through each piece.

Stayed at this property?
Wellfleet, Massachusetts, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
our trip coincided with a heat wave and the air conditioning was a blessing at night
Cleanliness:
the house is lovely very well-maintained clean and tastefully decorated
accurate listing clean cute good light
Host:
the owners are fantastic and incredibly responsive
Location:
great place for breakfast conversations and a resting break anytime
it was close to many excellent bayside and ocean beaches
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

3. Cozy cottage near beach (from USD 180)

This bright and airy 375-sq. ft. (35-sqm) cottage houses two bedrooms that can comfortably sleep up a small family. Attractions such as Mayo Beach and Indian Neck Beach are within a 1-mi (2-km) radius, so it will be easy for you and your loved ones to explore the town.

If you feel hungry after spending time on the beach and exploring the local attractions, you can prepare wholesome meals in the well-equipped kitchenette and have a scrumptious meal on the picnic table just outside the cottage!

Stayed at this property?
Wellfleet, Massachusetts, United States
cottage 4 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
comfortable beds n nice couch n open area
cottage interior very pleasant and with outdoor porch area picnic table area
on the positive side the cottage is tidy and comfortable
we were comfortable with this but i can understand that some folks want more choices than 10
the cottage is small but we were comfortable and had everything we need
Cleanliness:
and deep clean the upholstery
very bright and clean
it was very clean bright and near beaches restaurants town center
my wife & i did a full clean when we arrived in light of covid
the cottage is clean bright well-stocked with kitchen supplies and perfectly located
Host:
overall great stay & the owners were very accessible and super friendly
it feels very safe and friendly
Location:
the location is wonderful
it's location is ideal very near wellfleet center
cozy cottage close to bayside and wellfleet center attractions
this spot was enjoyable for its location to town
great location cute little quintessential cape cottage
Read more reviews
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4. Secluded house in a beautiful setting (from USD 239)

Although just a five-minute walk from the center of Wellfleet, this peaceful vacation rental is perfect for those who’re looking for an intimate time with their family. The property boasts an enchanting landscape, an expansive lawn, and a ‘secret garden’, making it ideal for a dreamy family vacation. Internet and indoor games are provided to ensure that the kids have entertainment once they’re tired from running outside.

There are only two bedrooms on the second floor, but the TV room on the first floor has a couch that can be transformed into a double bed. When it comes to baths, there are two indoor bathrooms and one outdoor shower. A total of eight guests can stay in this sweet home.

Stayed at this property?
Wellfleet, Massachusetts, United States
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Cleanliness:
supremely clean but comfortable
the rooms were beautiful simple but clean and comfortable beds
Host:
the owners were so pleasant to deal with; cordial and helpful
the owners were so pleasant to deal with; cordial and helpful
exceptionally well-appointed kitchen caring owners extremely comfortable and inviting wonderful porch overlooking lovely back yard walkable everywhere
Location:
walking distance to great seafood options
easy walk to town library restaurants galleries
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Recently renovated 19th-century home (from USD 230)

Sleeping up to eight adults, this spacious vacation rental has easy access to several beaches as well as local community centers such as Wellfleet Preservation Hall and Wellfleet Public Library. The property includes a parking space for three vehicles, so don’t fret if you and your company arrive by different cars.

The interiors of this 19th-century home have been newly remodeled to give you the best stay while staying true to its old charm. After taking a tour of Wellfleet, you can binge-watch your favorite series in the living area, but don’t forget to claim your bedroom! There are four bedrooms up for grabs and three baths, one of which has a double sink vanity and a bathtub where you can fully unwind.

Stayed at this property?
Wellfleet, Massachusetts, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
well appointed kitchen nice furnishings and art throughout
very nicely updated old house super comfortable for our large group
Cleanliness:
the property was well renovated clean and felt like home but also a vacation
Host:
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
Location:
the location is excellent
it’s steps to the town center and walking distance to everything including beaches we just love it here
it’s steps away from restaurants and shops and easy access to the beach
reviewer comments:this was such a hidden gem the location is amazing- right on the main street but still private
i was very happy with the location
Read more reviews
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6. Two-bedroom suite with private patio (from USD 199)

This lovely rental is located just a short walk from a secluded kettle pond that very few know about. You can access your suite through a private patio at the rear of the home. The hosts live on the premises, but your privacy and comfort are guaranteed.

Four guests staying at the rental will have access to a full bathroom, cable TV, mini fridge, electric kettle, and more. The hosts are also readily available to attend to your questions or needs. Need beach umbrellas or itinerary recommendations? Who better to ask than locals who have lived in the area for more than 30 years?

Stayed at this property?
Wellfleet, Massachusetts, United States
PRIVATE VACATION HOME 4 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Cleanliness:
this property is spotless comfortable and decorated perfectly for a relaxing stay with positive energy
accommodations are lovely: very clean with quality mattresses and bedding
Host:
owners provided excellent local restaurant and activities lists
the hosts are accommodating friendly helpful and unobtrusive
tons of recommendations and extremely helpful
Location:
beautiful national park near by
great cape location and awesome near by ice cream/ restaurants
the location is excellent and easy to find
great spot close to wellfleet in a quiet residential neighborhood
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

7. Picturesque cottage from the 1840s (from USD 115)

Wake up in this lovely cottage from the 1840s. The cottage has a white exterior and a warm-hued interior. The property features two bedrooms that can sleep a total of four guests, a bathroom, and a kitchen that leads to the dining area.

What’s best about this property? It is an Xplorie partner, meaning you get free equipment rentals and free admission to select local attractions and activities. Book this cottage for a complete vacation experience!

Stayed at this property?
Wellfleet, Massachusetts, United States
PRIVATE VACATION HOME 4 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
nice converted sleeping porch and comfortable main bedroom
Location:
upstairs bedroom stairs do require some flexibility (or shorter adults)easy walk to town and nearby harbor
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

8. Homey cedar cottage near a pond (from USD 195)

With two bedrooms and a loft bed, this peaceful cedar cottage can sleep up to six guests. You can easily enjoy a retreat with your loved ones as the property is surrounded by magnificent trees. There is a lush boardwalk just in front of the cottage where you can pass leisure time while admiring the community pond. There’s an opportunity for you to meet new people as well since there are more rental units around the pond!

Stayed at this property?
Wellfleet, Massachusetts, United States
143 reviews   Superhost Wifi Available
Entire cottage 5 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
very comfortable featuring many thoughtful amenities
cottage is far more adorable and comfortable then the photos reflect
wifi easily supported two people working at the same time
we loved eating at the picnic table on the back patio - beautiful and relaxing
the cottage was clean the wifi worked well and the kitchen was well stocked with tools
Cleanliness:
everything was super clean cozy conveniently located
this home was super clean spacious and easy to find
the cottage is very clean and the linens are fresh
it was super clean well-stocked and in a great location
our weekend stay was excellent the home was clean neat and so very comfortable
Host:
sarah and christian were excellent hosts
sarah and christian were excellent hosts and communicated often and quickly with us
host was extremely communicative and helpful
nice home convenient launch point for things to do communicative hosts
would highly recommend this airbnb hosts are great and communicated everything clearly
Location:
wonderful house in a beautiful location
the location is fantastic as well
a beautiful wooden cabin in a really great location
beautiful place very baby friendly near the woods and near the highway and near everything
very cute and cozy place to stay
Read more reviews

9. Beachfront bungalow for families (from USD 275)

Book this self-check-in bungalow if you enjoy falling asleep to the sound of waves. This property is well maintained and is equipped with everything you’ll need for a pleasant stay - from quality kitchen appliances to extra pillows and blankets. It can sleep up to four guests, but you can rent a second cottage if your family has more members.

Don’t forget to enjoy a barbeque with your folks or have a lovely family time by the firepit in the backyard!

Stayed at this property?
Wellfleet, Massachusetts, United States
94 reviews   Superhost Wifi Available
Entire bungalow 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the beds are most comfortable the cottage is immaculate and there is a beautiful outdoor space
we made good use of the grill and picnic table to enjoy the beautiful weather
this cottage is sweet cozy and so well-maintained
the cottage is cozy but she has thought of everything and makes good use of the space
rosemary’s cottage is cute cozy and well stocked
Cleanliness:
clean well appointed great spot
the house is clean and well equipped for a cozy romantic getaway
wonderful cozy clean and comfortable with a great location
the cottage is so clean comfortable and cozy and is outfitted with anything you might need
the cottage was impeccably clean well equipped and in a great location on the cape
Host:
wonderfully attentive host
perfect getaway with great host
rosemary is a exceptionally wonderful host
rosemary is a wonderful host who makes everything easy
rosemary is a very thoughtful host
Location:
ideal location (literally across the street from mayo beach)
there are also 3 great restaurants within walking distance of the house
it has everything you need and is super close to the beach
location right across from a lovely beach can't be beat
nice cottage on a beautiful bay walking distance from town lovely garden
Read more reviews

10. Sweet hideaway for couples (from USD 169)

Tucked behind a historic house, this sweet and snug property is perfect for couples or small families who need relaxation. Keep in mind that for bookings of three to four people, there’s an extra charge of 12 USD per person per night for extra towels and linens.

Even with more people, you’ll still have an abundance of space in this home! The screened porch and the private backyard provide perfect spots for taking a break and soaking in the serene greenery of the surroundings.

Stayed at this property?
Wellfleet, Massachusetts, United States
82 reviews   Superhost Wifi Available
Entire guesthouse 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the bed was so comfortable and the porch and outdoor space were lovely
it's as nice as if not nicer than the listing shows and the bed is extremely comfortable
Cleanliness:
everything was clean and the bed comfortable
great space clean up to date and comfortable
clean and so many thoughtful touches: quality of dishes/silverware beach chairs tissues spices and linens
this place is awesome super clean
lovely all around great hosts super clean easy and quick communication loved it
Host:
david and betsy are wonderful and kind
responsive and friendly hosts
david and betsy are kind thoughtful and considerate hosts
very communicative hosts with great tips on local spots
david betsy were great hosts they were great with communicating before check in as well
Location:
located in wellfleet ma this location is ideal
cute little cottage close to downtown wellfleet
great location in wellfleet
easy walk to downtown area
very cute place and you can’t beat the location
Read more reviews

Prioritize wellness in Wellfleet

With its array of spectacular beaches, sweet local scenes, and delectable shellfish offerings, Wellfleet will surely have you looking forward to ticking off another box on your bucket list. Make sure to book one of these vacation rentals, so you can fully recharge after a long day and prepare for the next day’s adventure.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Louisse has always loved writing, which started in her little diaries, where she talked about her many dreams. These dreams included writing for a living and, of course, traveling. She still has so...Read more

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