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
per person
21 Sept - 26 Sept
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9/10 Wonderful! (2,101 reviews)
The bed is comfortable, bathrooms are always clean. The front desk was very kind.

Reviewed on 16 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
21 Sept - 26 Sept
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on 11 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
26 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Beautiful building, friendly staff, great atmosphere

Reviewed on 16 Aug 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
per person
21 Sept - 26 Sept
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.2/10 Wonderful! (1,102 reviews)
Good location but expensive.

Reviewed on 16 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
26 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
The beds are the main thing that keep me coming black, so comfortable, especially after a long day of walking around Boston. I will say we were disappointed that the inside of our coffee machine was very dirty.. something i think shouldn't be missed when cleaning since we love a good morning coffee in the room , but had to settle for going to a coffee shop. We tried ordering room service , but after waiting over 1hr we ended up calling to cancel it. For the amount of money we paid , i think they could step their game up when it comes to service and details.

Reviewed on 16 Aug 2025

Top hotels in Pleasant Point

Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St, Provincetown, MA
Fully refundableReserve now, pay when you stay
The price is €222 per night from 4 Sept to 5 Sept
€222
4 Sept - 5 Sept
includes taxes & fees
7.8/10 Good! (1,010 reviews)
"We stayed for 3 nights and had a mostly wonderful experience. There are a few things that could be improved and would have been helpful to know. 1) the lobby which has a microwave and toaster is only open from 8’am-10 pm. There is a fridge and keurig in the room but otherwise no option to heat any ..."

Reviewed on 17 Aug 2025

Harbor Hotel Provincetown
Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
Fully refundableReserve now, pay when you stay
7.6/10 Good! (1,009 reviews)
"The room was large and adequate. The bed was quite stiff. Room smelled of cleaning fluid."

Reviewed on 17 Aug 2025

Get rates
Captains Quarters Motel & Conference Center
The Provincetown Inn

The Provincetown Inn

3 out of 5
1 Commercial Street, Provincetown, MA
Fully refundableReserve now, pay when you stay
The price is €218 per night from 16 Sept to 17 Sept
€218
16 Sept - 17 Sept
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Beautiful sunrise and sunset views from the rooms. Pool was relaxing and bartenders were terrific. The walk to town was a little longer than expected, but was a quick Uber or shuttle ride."

Reviewed on 15 Aug 2025

The Provincetown Inn
See all 4,343 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 €970, 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

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.