Pleasant Point Holidays

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Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was €1,061, price is now €786 per person
€786
per person
25 Mar - 29 Mar
found 4 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
Excellent value for the price. The lobby was well decorated. Would love to stay again.

Reviewed on 7 Jan 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was €1,369, price is now €961 per person
€961
per person
25 Mar - 29 Mar
found 4 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Our second stay there, love it

Reviewed on 25 Dec 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was €1,049, price is now €834 per person
€834
per person
25 Mar - 29 Mar
found 4 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
As always, i love to stay at The Colonnade!

Reviewed on 8 Jan 2026

The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was €1,097, price is now €890 per person
€890
per person
25 Mar - 29 Mar
found 4 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
Clean room, amazing staff, fun lobby bar!

Reviewed on 8 Jan 2026

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was €1,106, price is now €904 per person
€904
per person
25 Mar - 29 Mar
found 4 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (621 reviews)
The area around the property was excellent. It felt very safe and quiet, with plenty of shopping and dining options nearby. Everything was walkable, which made the stay very convenient. Parking was easy, and transportation access was great. Overall, a great location and an enjoyable stay.

Reviewed on 1 Jan 2026

Top hotels in Pleasant Point

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is €357 per night from 14 Jan to 15 Jan
€357
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
Modern Beachfront Condo, Gorgeous Views and Centrally Located

Modern Beachfront Condo, Gorgeous Views and Centrally Located

Provincetown MA
9.8/10 Exceptional! (59 reviews)
It was a great view, though we had a good look at a sauna/polar plunge group every day, hosted by a local yoga studio, that operated right behind our harborside window. Parking is a 5 minute walk away, but it is a very walkable area and you can do many things without driving anywhere. The flat is ...

Reviewed on 29 Dec 2025

Get rates
Modern Beachfront Condo, Gorgeous Views and Centrally Located
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street Brewster MA
The price is €194 per night from 19 Jan to 20 Jan
€194
19 Jan - 20 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
See all 4,160 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 €786, 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 1,000,000 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

Enjoy a relaxing day at the beach and a lively night at the bar at this favorite daytrip destination.

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

Wellfleet Harbor Actors Theater

You can make plans for a show at Wellfleet Harbor Actors Theater during your trip to Wellfleet. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Wellfleet Harbor Actors Theater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.