Hotels Near
Pleasant Point

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured Pleasant Point Hotels

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
Stay at this 5-star luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
9/10 Wonderful! (791 reviews)
Excellent experience all around Gorgeous location and beautiful hotel Lively lobby

Reviewed on Oct 13, 2025

Chatham Bars Inn
Surfside Hotel and Suites

Surfside Hotel and Suites

2.5 out of 5
543 Commercial Street, Provincetown, MA
Book a stay at this beach hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.4/10 Very Good! (1,001 reviews)
It was a very nice room right on the water. Everyone was very nice.

Reviewed on Oct 17, 2025

Surfside Hotel and Suites
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
Stay at this 4-star golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
9.2/10 Wonderful! (577 reviews)
Pillows are terrible; so hard.

Reviewed on Oct 23, 2025

Chatham Wayside Inn
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
2173 Head of the Bay Road, Route 28, Harwich, MA
Stay at this 5-star luxury resort in Harwich. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Captain's Cove Golf Course and Caleb Nickerson ...
9.2/10 Wonderful! (241 reviews)
There is no finer place. Everything is tastefully appointed. Food is phenomenal. Staff could not be more helpful and they are always smiling- extremely professional. The food is over the top designed and tasteful. If you love luxury and a great night’s sleep in a most comfortable bed- this is the ...

Reviewed on Oct 18, 2025

Wequassett Resort and Golf Club
Wellfleet Motel and Lodge

Wellfleet Motel and Lodge

2.5 out of 5
170 US 6, Wellfleet, MA
Stay at this motel in Wellfleet. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,010 reviews)
Breakfast has closed for the season. Location was convenient on Route 6, but removed from the highway noise. Room was clean and had nice tv with plenty of channels plus microwave and refrigerator. Bathroom and shower had everything I needed.

Reviewed on Oct 27, 2025

Wellfleet Motel and Lodge
Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
Book a stay at this business-friendly hotel in Eastham. Enjoy free WiFi, free parking, and a conference center. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (1,000 reviews)
Everything was comfortable, very nice front desk person

Reviewed on Oct 18, 2025

Captains Quarters Motel & Conference Center
Sandcastle Resort and Club

Sandcastle Resort and Club

3 out of 5
929 Commercial Street, Provincetown, MA
Stay at this 3-star beach aparthotel in Provincetown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (1,127 reviews)
Staff was very helpful. Rooms are good. Beach was in walking distance.

Reviewed on Oct 22, 2025

Sandcastle Resort and Club
Cape Colony Inn

Cape Colony Inn

2.5 out of 5
280 Bradford Street, Provincetown, MA
Stay at this hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,039 reviews)
.

Reviewed on Oct 24, 2025

Cape Colony Inn
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street, Brewster, MA
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (1,000 reviews)
Highly recommend. From check in to check out, the service was friendly, responsive and courteous. The room was also a great surprise. Large room with a large bathroom.Well appointed with a nice balcony. Good bathroom lighting for make-up and easy for two people to get ready at the same time. Beds ...

Reviewed on Sep 22, 2025

The Mansion at Ocean Edge
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St, Provincetown, MA
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Provincetown. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the pool and the helpful staff in ...
8/10 Very Good! (1,001 reviews)
The staff were very friendly and helpful. The room had been updated recently and was clean and pleasant. The view of the ocean was lovely.

Reviewed on Oct 24, 2025

Harbor Hotel Provincetown
The Provincetown Inn

The Provincetown Inn

3 out of 5
1 Commercial Street, Provincetown, MA
Fully refundableReserve now, pay when you stay
Stay at this 3-star beach hotel in Provincetown. Enjoy an outdoor pool, 3 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in ...
8/10 Very Good! (1,014 reviews)
Great place

Reviewed on Oct 24, 2025

The Provincetown Inn
Top Mast Resort

Top Mast Resort

2.5 out of 5
209 Shore Rd, North Truro, MA
Book a stay at this beach hotel in North Truro. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (835 reviews)
It was absolutely beautiful. I i didn't dislike anything. It was a beautiful stay. The staff was friendly. The beach was amazing. The sunsets. It was very clean and comfortable, and when I thank everyone that I interacted with and thank you for such a beautiful, amazing stay.And so deeply so powerful, ...

Reviewed on Oct 22, 2025

Top Mast Resort
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.

Hotels in Pleasant Point

Wellfleet is a city that has a lot going on, but you have your sights set on Pleasant Point. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Pleasant Point has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Pleasant Point hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Wellfleet so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Pleasant Point underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Pleasant Point city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Pleasant Point cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Pleasant Point at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $102
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Pleasant Point hotel you want, book it, and never look back. Because your great escape is ahead of you.