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! (807 reviews)
Beautiful property

Reviewed on Jan 24, 2026

Chatham Bars Inn
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! (626 reviews)
Courteous staff, helpful with dining suggestions. Loved the room. Very comfortable bed, warm and cozy.

Reviewed on Jan 29, 2026

Chatham Wayside 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! (1,002 reviews)
Didnt overlook beach.

Reviewed on Jan 21, 2026

The Mansion at Ocean Edge
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! (299 reviews)
It was an excellent time, I wish the bed was a king size, but I would would definitely stay again.

Reviewed on Jan 18, 2026

Edgewater Beach Resort, a VRI 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! (244 reviews)
The staff is amazing, they are kind and always looking for ways to help and make you feel welcome.

Reviewed on Jan 1, 2026

Wequassett Resort and Golf 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! (1,000 reviews)
We had this place to our selves. Since our stay was the last one till spring. Luis the manager was phenomenal extremely friendly and made sure we were all set. The breakfast was truly great. Had a great conversation with Luis at Breakfast It was a wonderful stay a will be back soon

Reviewed on Jan 5, 2026

Cape Colony Inn
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! (873 reviews)
Very clean, great location.

Reviewed on Jan 26, 2026

Four Points by Sheraton Eastham Cape Cod
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
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! (483 reviews)
Amazing. As always! <3

Reviewed on Jan 25, 2026

Mercury Hotel Provincetown
Ellery Hotel Provincetown

Ellery Hotel Provincetown

4 out of 5
14 Johnson Street Provincetown MA
Fully refundableReserve now, pay when you stay
Book a stay at this boutique B&B in Provincetown. Enjoy free WiFi, free parking, and a sauna. Popular attractions Provincetown Public Library and Packard Gallery ...
9.4/10 Exceptional! (368 reviews)
We stayed one frigid January night - we truly appreciated the fireplace in the room. What a beautiful spot! Quiet, central, very well-appointed.

Reviewed on Jan 25, 2026

Ellery Hotel Provincetown
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! (999 reviews)
The staff were all lovely. Our room was facing the water and that was a great perk. It’s a bit away from the downtown area but it’s one of the bike and scooter stops so we enjoyed that. We will stay here again!

Reviewed on Oct 31, 2025

Surfside Hotel and Suites
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! (848 reviews)
We had a great room (king superior) that was spacious, clean and quiet. The bed was comfortable and the staff and management were incredibly friendly and welcoming. Would definitely stay here again!

Reviewed on Jan 2, 2026

Crowne Pointe Historic Inn & Spa - Adults Only
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 $125
  • 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.