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 10.746.720 ₫ per night from 23 Apr to 24 Apr
10.746.720 ₫
12.299.622 ₫ total
23 Apr - 24 Apr
includes taxes & fees
9.2/10 Wonderful! (818 reviews)
Spa suite was awesome after we were changed from 603 (that had a generator outside the wall of the bedroom) to 604 (that had a serene view of the Zen garden), food was delicious but expensive, and staff was courteous. We were there off season, everything closed in the area, so nothing to do outside ...

Reviewed on 12 Apr 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is 4.243.052 ₫ per night from 5 May to 6 May
4.243.052 ₫
6.001.641 ₫ total
5 May - 6 May
includes taxes & fees
9.2/10 Wonderful! (650 reviews)
Clean and up to date room and property in general. Continental Breakfast was very good and all staff helpful and polite

Reviewed on 4 Apr 2026

Chatham Wayside Inn
Cape Colony Inn

Cape Colony Inn

2.5 out of 5
280 Bradford Street Provincetown MA
The price is 1.817.322 ₫ per night from 29 Apr to 30 Apr
1.817.322 ₫
2.079.912 ₫ total
29 Apr - 30 Apr
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Everything was great. The staff were very helpful, the room was clean, the bad was comfy, the fire pit was cozy. My only problem was the breakfast. It wasn’t really a breakfast but more like a snack. There were no hot options. Otherwise everything was great.

Reviewed on 13 Apr 2026

Cape Colony Inn
See all 4,258 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

Sand Dunes, Marconi Beach, Cape Cod National Seashore, Wellfleet

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
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
Wellfleet, Massachusetts, US August15, 2017 Wellfleet Preservation Hall, Cape Cod MA US.

Wellfleet Preservation Hall

Wellfleet Preservation Hall is just one of the places to see in Wellfleet, so why not enjoy the other things to explore during your travels? Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Wellfleet Preservation Hall