Pleasant Point Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Pleasant Point

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is 9.560.824 ₫ per night from 14 Jan to 15 Jan
9.560.824 ₫
10.942.363 ₫ total
14 Jan - 15 Jan
includes taxes & fees
9/10 Wonderful! (802 reviews)
Room was very clean but a little dated also there is very little space to put your clothes away…no dressers

Reviewed on 3 Jan 2026

Chatham Bars Inn
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street Brewster MA
The price is 3.813.556 ₫ per night from 25 Jan to 26 Jan
3.813.556 ₫
5.867.819 ₫ total
25 Jan - 26 Jan
includes taxes & fees
8.2/10 Very Good! (999 reviews)
Over the top, Mansion full of history, c Great food, wonderful view of bay water. Best bread pudding ever! And what a surprise when we found our room stocked with wine, chocolates, nuts fruits cheese and cake in honor of our 52 nd anniversary, with a card! ALWAYS WANTED TO STAY THERE, M NOW I WILL ...

Reviewed on 3 Jan 2026

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
The price is 3.103.328 ₫ per night from 12 Jan to 13 Jan
3.103.328 ₫
4.693.997 ₫ total
12 Jan - 13 Jan
includes taxes & fees
9.2/10 Wonderful! (614 reviews)
I’ve always been curious about the Wayside Inn because my mom worked there a gazillion years ago when she was in high school. It’s so cozy and clean and staff was very friendly. They also upgraded us which was super nice! The only thing was outlets in the room were kind of oddly positioned— but we ...

Reviewed on 4 Jan 2026

Chatham Wayside Inn
See all 4,156 properties in Pleasant Point
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.

Frequently asked questions

How much does a Pleasant Point holiday package cost?
The cheapest Pleasant Point holiday package is , so your dream trip can become a reality — without spending an arm and a leg. Bundle flights, hotels, car rentals and more to tailor a package that's perfect for you.
How do I get a cheap travel package to Pleasant Point?
You'll save tons of cash if you combine your flights, car rentals and hotels into a Pleasant Point holiday package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer more than 550 airlines and 1null000null000 hotels worldwide, so you'll always have plenty of options to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Pleasant Point?
A trip to Pleasant Point wouldn't be complete without stopping by Mayo Beach, Indian Neck Beach and Wellfleet Harbour Actors Theatre. Spend your nights near these popular sights and make sightseeing simple.
What are the top hotels in Pleasant Point?
If it's comfort and convenience you're after, look no further than Waterfront Views Of Creek - Beach Access. Spend your nights relaxing here and your days wandering around Pleasant Point's most well-known attractions.
How far in advance should I book my Pleasant Point holiday?
It's difficult to pick the ideal time for airfares, but we normally say the earlier, the better. Plenty of international journeys on Expedia become available up to 12 months in advance. If you can't book ahead, don't fret. Budget prices appear from time to time just weeks before departure dates.
What does an Expedia Pleasant Point travel package include?
Flights, hotels and rental cars — we've got them well covered. With Expedia, you can shape your Pleasant Point travel package however you want. All you have to do is figure out just what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the greater your savings!
What should I know before booking a Pleasant Point travel package?
You can save big by combining your flights, hotels and rental cars. Once you've made your booking, you can add on things like tours and activities. Your next unforgettable holiday is only a few clicks away.
Can I choose my airline with a Pleasant Point Expedia holiday package?
Yes, and with more than 550 airlines to pick from throughout the world, you've got lots of choice. Browse the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Pleasant Point holiday package?
Don't worry if you're rethinking your Pleasant Point holiday package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We know your circumstances can suddenly change, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Popular places to visit

Cahoon Hollow Beach

Cahoon Hollow Beach

Why not spend a care-free afternoon at Cahoon Hollow Beach during your travels in Wellfleet? Discover the area's seafood restaurants or seek out the hiking trails.

Cahoon Hollow Beach
Beach

Beach

Why not spend a care-free afternoon at Beach during your travels in Wellfleet? Discover the area's seafood restaurants or seek out the hiking trails.

Beach
Mayo Beach

Mayo Beach

If a restful holiday is part of your travel plans, Mayo Beach might be the perfect place to visit during your trip to Wellfleet. Discover the area's seafood restaurants or seek out the hiking trails.

Mayo Beach