Hotels Near
Pleasant Point

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Featured Pleasant Point Hotels

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (798 reviews)
An incredible stay. Room at the main inn could use some updating. Just a bit tired with cracked tiles and some worn furniture, but overall the hotel is spectacular. The breakfast at Stars was amazing.

Reviewed on Dec 14, 2025

Chatham Bars 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)
The hotel is beautifully decorated for the holiday season

Reviewed on Dec 17, 2025

The Mansion at Ocean Edge
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
Book a stay at this 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! (608 reviews)
After initial hiccup with the room which was taken care off - room was beautiful as well as the Inn. Best location on Main Street in Chatham.

Reviewed on Dec 23, 2025

Chatham Wayside Inn
The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort

2.5 out of 5
41 Chase Ave Dennis Port MA
Book a stay at this beach hotel in Dennis Port. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Sea Street Beach and Cape Cod Theatre ...
8.4/10 Very Good! (222 reviews)
Clean and comfortable

Reviewed on Nov 6, 2025

The Corsair & Cross Rip Oceanfront Resort
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
2173 Head of the Bay Road, Route 28 Harwich MA
Book a stay at this luxury resort in Harwich. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Captains Golf Course and Chatham Marconi ...
9.2/10 Wonderful! (243 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
Breakwater Hotel

Breakwater Hotel

2.5 out of 5
716 Commercial St Provincetown MA
Book a stay at this beach motel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
9.4/10 Exceptional! (631 reviews)
As always, the room was spotless and cozy. Such lovely decor and quality everything. The huge bed, lush linen, perfect selection of pillows. Breakfast offers a generous variety of healthy choices. Amazing location. Sunsets. Starlight. Grateful for the friendly, hardworking Breakwater staff. These ...

Reviewed on Dec 20, 2025

Breakwater Hotel
Crowne Pointe Historic Inn & Spa - Adults Only

Crowne Pointe Historic Inn & Spa - Adults Only

4 out of 5
82 Bradford Street Provincetown MA
Book a stay at this spa hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (843 reviews)
Chris at the front desk was amazing, he made our trip. Our room was cozy and the services, complimentary breakfast, wine and cheese hour made the stay wonderful. Easy walking the tie, great location!

Reviewed on Dec 3, 2025

Crowne Pointe Historic Inn & Spa - Adults Only
Four Points by Sheraton Eastham Cape Cod

Four Points by Sheraton Eastham Cape Cod

3 out of 5
3800 State Hwy Eastham MA
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Eastham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (858 reviews)
The room was clean. When we arrived the TV did not work. When I tried to call the front desk from the room phone, the phone did not work. We went to the front desk and had maintenance show up immediately. The TV needed to be plug in, but the phone was dead, so we told them not to worry, we had cell ...

Reviewed on Nov 28, 2025

Four Points by Sheraton Eastham Cape Cod
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. ...
9/10 Wonderful! (1,002 reviews)
Great location, easy check-in and so clean.

Reviewed on Dec 21, 2025

Cape Colony Inn
Bluebird Dennisport

Bluebird Dennisport

3 out of 5
426 Lower County Rd Dennis Port MA
Stay at this hotel in Dennis Port. Enjoy free WiFi, an outdoor pool, and housekeeping. Popular attractions Cape Cod Theatre Company – Home of the Harwich Jr. ...
8.4/10 Very Good! (219 reviews)
Wonderful cottage with all amenities and renovated beautifully

Reviewed on Oct 9, 2025

Bluebird Dennisport
Edgewater Beach Resort, a VRI resort

Edgewater Beach Resort, a VRI resort

3.5 out of 5
95 Chase Avenue Dennis Port MA
Book a stay at this beach aparthotel in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Pleasant Road Beach and Cape Cod ...
8.8/10 Excellent! (296 reviews)
room was nice and spacious for our family. Resort is right on the beach. Early quiet hours of 10 pm on a weekend

Reviewed on Dec 21, 2025

Edgewater Beach Resort, a VRI resort
Mercury Hotel Provincetown

Mercury Hotel Provincetown

3 out of 5
12 Winthrop St. Provincetown MA
Fully refundableReserve now, pay when you stay
Stay at this guesthouse in Provincetown. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (476 reviews)
Great stay! Upgraded room!

Reviewed on Dec 16, 2025

Mercury Hotel Provincetown
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.