Pleasant Point Holidays

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Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was €1,525, price is now €1,200 per person
€1,200
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
17.2/10 Exceptional! (1,337 reviews)
Staff were very courteous! Clean room!

Reviewed on 15 Nov 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was €1,678, price is now €1,305 per person
€1,305
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
19.2/10 Exceptional! (482 reviews)
The room was wonderful, the bed was heaven. Room service was delicious and the overall aesthetic and ambience of the lobby and common areas were fabulous

Reviewed on 18 Nov 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was €1,790, price is now €1,460 per person
€1,460
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
19.2/10 Exceptional! (1,004 reviews)
The Langham, Boston is fantastic! Friendly staff and very clean environment for Business or leisure.

Reviewed on 18 Nov 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was €1,463, price is now €1,234 per person
€1,234
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
18.4/10 Exceptional! (2,268 reviews)
Room was really clean!!

Reviewed on 17 Nov 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €1,610, price is now €1,367 per person
€1,367
per person
27 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
19.6/10 Exceptional! (1,005 reviews)
Beautiful room with a view. The fitness center and spa was great!

Reviewed on 17 Nov 2025

Top hotels in Pleasant Point

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is €270 per night from 20 Nov to 21 Nov
€270
20 Nov - 21 Nov
includes taxes & fees
9.2/10 Wonderful! (794 reviews)
Great accommodation and staff.

Reviewed on 8 Nov 2025

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is €158 per night from 23 Nov to 24 Nov
€158
23 Nov - 24 Nov
includes taxes & fees
9.2/10 Wonderful! (591 reviews)
Our room was nicely appointed and an excellent layout.

Reviewed on 13 Nov 2025

Chatham Wayside Inn
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
2173 Head of the Bay Road, Route 28 Harwich MA
9.2/10 Wonderful! (241 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 18 Oct 2025

Get rates
Wequassett Resort and Golf Club
See all 4,164 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 €1,200, 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.