Pleasant Point Holidays

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

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was €857, price is now €558 per person
€558
per person
18 Feb - 23 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
Room was very comfortable & clean.Staff was great.Food & drinks outstanding.Very festive atmosphere at the Lenox.Great time to be in Boston,the night before New Year’s Eve.

Reviewed on 1 Jan 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €2,070, price is now €1,051 per person
€1,051
per person
18 Feb - 23 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The location, the service, the view, the little things were all outstanding!

Reviewed on 31 Dec 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was €1,695, price is now €1,080 per person
€1,080
per person
18 Feb - 23 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Amazing week - family stay for Christmas in town - thank you very much! We’ll be back!…….

Reviewed on 28 Dec 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was €1,273, price is now €812 per person
€812
per person
18 Feb - 23 Feb
found 1 day ago
Return direct 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 Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was €1,492, price is now €1,032 per person
€1,032
per person
18 Feb - 23 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
All good. Excellent staff. Very crowded at entry.

Reviewed on 2 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 €452 per night from 10 Jan to 11 Jan
€452
10 Jan - 11 Jan
includes taxes & fees
9/10 Wonderful! (801 reviews)
Rooms were quaint, clean, and unique. Will definitely be staying again!!

Reviewed on 30 Dec 2025

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)
We spent a long weekend at John’s condo and it is better than the pictures! Besides the absolutely amazing views of the pier, the condo was comfortable and had beautiful touches of luxury all around. The kitchen was well stoked and allowed for cooking chefs style. The bedroom was cozy and the mattress ...

Reviewed on 23 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 €202 per night from 11 Jan to 12 Jan
€202
11 Jan - 12 Jan
includes taxes & fees
8.2/10 Very Good! (999 reviews)
The hotel is beautifully decorated for the holiday season

Reviewed on 17 Dec 2025

The Mansion at Ocean Edge
See all 4,183 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 €558, 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.