A row of historic houses with gabled roofs and white trim, surrounded by lush greenery and a well-maintained hedge.

Wellfleet Holiday Rentals

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Our top choices for Wellfleet holiday rentals

1. Waterfront Cottage - fantastic unobstructed views!!

Waterfront Cottage - fantastic unobstructed views!!
Wellfleet
9.8 out of 10, Exceptional, (84 reviews)
"Perfect location, beautiful views, clean and comfortable. "
United States
Lori H.
The price is NZ$2,119
includes taxes & fees
22 Aug - 23 Aug
Waterfront Cottage - fantastic unobstructed views!!

2. On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (63 reviews)
"Clean, great location. "
United States
Peter G.
On Town Cove with salt water access! Kayaks and paddle board available for use!

3. Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,232 reviews)
"Location small drive to all the activities and down town Fun experience"
United States
debra
The price is NZ$313
includes taxes & fees
13 Sept - 14 Sept
Sandcastle Resort and Club

4. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (140 reviews)
"Nice resort. Well maintained, very quiet, off the beaten path. Everything in good working order, Staff very nice. Will stay here again. Great location!"
United States
Kevin
The price is NZ$448
includes taxes & fees
15 Sept - 16 Sept
Brewster Green Resort

5. Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Eastham
10.0 out of 10, Exceptional, (21 reviews)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is NZ$980
includes taxes & fees
9 Sept - 10 Sept
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

6. Castaway Cottage on the bay~Dog Friendly Too!

Castaway Cottage on the bay~Dog Friendly Too!
Eastham
9.8 out of 10, Exceptional, (18 reviews)
"Cottage was quaint. The location was amazing - very peaceful and quiet. Our favorite place to sit was in the two swinging chairs overlooking the bay. The sunsets were absolutely amazing. We really enjoyed our stay and hope to be back."
United States
Patty M.
Castaway Cottage on the bay~Dog Friendly Too!

7. Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
9.8 out of 10, Exceptional, (10 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is NZ$1,173
includes taxes & fees
23 Aug - 24 Aug
Great for Families! Brewster Home 6 Mi to Beach

8. 6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is NZ$1,171
includes taxes & fees
23 Aug - 24 Aug
6 Mi to Beach: Home w/ Deck in Brewster!

9. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (26 reviews)
"Perfect size home for a family of 4, welcoming and cozy! Having -All towels and linens and shampoo, body wash and conditioner all included made for a much easier stay! Highly recommend."
United States
Emily A.
The price is NZ$903
includes taxes & fees
13 Sept - 14 Sept
🦀Waterfront at The Velvet Crab~Amazing Sunsets

10. Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (33 reviews)
"We had a lovely visit with access to the beach and very comfortable beds. Enjoyed a beautiful sunset!"
United States
Debra H.
The price is NZ$1,410
includes taxes & fees
30 Aug - 31 Aug
Sand Bar-Dog Friendly on Cooks Brook Beach

11. The Breeze on Minister's Pond

The Breeze on Minister's Pond
Eastham
10.0 out of 10, Exceptional, (26 reviews)
"The Breeze is the cutest, warmest, comfiest home. We thoroughly enjoyed our stay and will definitely book again!"
United States
MelanieC
The price is NZ$1,165
includes taxes & fees
4 Sept - 5 Sept
The Breeze on Minister's Pond

12. Waterfront~Dog Friendly~ Lieutenant's Lodge

Waterfront~Dog Friendly~ Lieutenant's Lodge
Wellfleet
9.8 out of 10, Exceptional, (15 reviews)
"Great home for a relaxing weekend"
United States
Mike B.
The price is NZ$1,356
includes taxes & fees
29 Aug - 30 Aug
Waterfront~Dog Friendly~ Lieutenant's Lodge

13. Quiet getaway in a unique area of Cape Cod

Quiet getaway in a unique area of Cape Cod
Brewster
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for a quiet getaway. Owner was in Constant contact. If I had a question replied very quickly. I highly recommend staying here."
United States
Anonymous traveller
The price is NZ$792
includes taxes & fees
29 Aug - 30 Aug
Quiet getaway in a unique area of Cape Cod

14. Luxury 2-Story PTown Condo: 5 Min Walk to Commercial St. Private Patio & Parking

Luxury 2-Story PTown Condo: 5 Min Walk to Commercial St. Private Patio & Parking
Provincetown
10.0 out of 10, Exceptional, (33 reviews)
"We had an excellent stay! The property was beautiful, clean, and in a great location. We would absolutely stay here again. "
United States
Kristen W.
The price is NZ$817
includes taxes & fees
13 Sept - 14 Sept
Luxury 2-Story PTown Condo: 5 Min Walk to Commercial St. Private Patio & Parking

15. Walk to Commercial Street! Couples Retreat w/ Deck

Walk to Commercial Street! Couples Retreat w/ Deck
Provincetown
8.4 out of 10, Very good, (24 reviews)
"The place is really cute, super clean and a wonderful location!! The available parking is great! "
United States
Kelleigh M.
The price is NZ$1,020
includes taxes & fees
26 Aug - 27 Aug
Walk to Commercial Street! Couples Retreat w/ Deck

16. Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (13 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is NZ$892
includes taxes & fees
7 Sept - 8 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort

17. Gorgeous waterfront studio w/ beach access sitting on downtown Commercial Street

Gorgeous waterfront studio w/ beach access sitting on downtown Commercial Street
Provincetown
9.0 out of 10, Wonderful, (32 reviews)
"The place was very nice and in a great central location and very convenient. Took a moment for me to discover that there were Murphy beds. I suggest you put a little sign or instructions. Place was very clean, well decorated and well equipped for cooking and a longer stay than mine. Wished it had parking, but public parking was pretty nearby. I had my bike and locked it there. Overall too brief but a nice stay."
United States
Peter
The price is NZ$950
includes taxes & fees
14 Sept - 15 Sept
Gorgeous waterfront studio w/ beach access sitting on downtown Commercial Street

18. Walk to Commercial Street! Couples Retreat w/ Deck

Walk to Commercial Street! Couples Retreat w/ Deck
3.0 star property
Provincetown
The price is NZ$1,042
includes taxes & fees
26 Aug - 27 Aug
Walk to Commercial Street! Couples Retreat w/ Deck

19. 2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Eastham
10.0 out of 10, Exceptional, (47 reviews)
"Kitchen was well equipped. Very good location for us and comfy beds. I highly recommend this property and the host. "
United States
Mark T R.
The price is NZ$1,727
includes taxes & fees
6 Sept - 7 Sept
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

20. Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch

Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch
Eastham
9.0 out of 10, Wonderful, (102 reviews)
"Awesome location, private and peaceful."
United States
Kathy D.
The price is NZ$965
includes taxes & fees
1 Sept - 2 Sept
Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wellfleet Hotel Reviews

Find out more about Wellfleet

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wellfleet holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wellfleet. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wellfleet. Seeing all the best attractions is bound to make you fall in love with Wellfleet. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wellfleet short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a holiday rental in Wellfleet?

Yes, there are holiday rentals close to the most popular sights in Wellfleet, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Wellfleet speak positively about the beaches and seafood restaurants in this destination. Make sure you have time to check out the entertainment choices and waterfront during your trip.

What are some of the best holiday rentals that Wellfleet has to offer?

Family & Pet Getaway | Scenic Views |Cape Cod Home: This highly rated holiday home rental in Wellfleet has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Wellfleet?

Expedia has 228 holiday rentals for your stay in Wellfleet.

What’s there to see and do in Wellfleet?

Enjoy the outdoors at Cape Cod Beaches and Mayo Beach, or simply take in cultural attractions like Wellfleet Harbor Actors Theater and Wellfleet Historical Society Museum. Other places in town to visit include Cape Cod National Seashore and Cahoon Hollow Beach.

What’s a holiday rental in Wellfleet like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wellfleet. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for small groups.