Pleasant Point Holidays from £990

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Your Pleasant Point Holiday

Discover the wonders of Pleasant Point with a customized Pleasant Point holiday package. From its nature to its views and beyond, this neighbourhood offers plenty of opportunities for relaxation and adventure. Some top nearby attractions to check out during your trip to Pleasant Point include Marconi Beach, Cahoon Hollow Beach and Indian Neck Beach. Expedia can help turn your ideal Pleasant Point holiday into reality, no matter your travel plans or budget.

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

The Beverly

3 out of 5
per person
17 Oct - 21 Oct
found 1 day ago
Return direct flight included
London (LON) to Boston (BOS)
8.4/10 Very Good! (323 reviews)
Stopped in for overnight stay. Awkward check in as no emailed code (no desk staff on premises), got that worked out. Rooms are comfortable and appeared clean. Couple of places across street to eat and little shopping center, so nice options for quick stay.

Reviewed on 31 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
5 Sept - 8 Sept
found 17 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Favorite hotel in Boston amazing pool and gym

Reviewed on 2 Aug 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
18 Oct - 25 Oct
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
per person
18 Oct - 25 Oct
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
7.4/10 Good! (114 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on 23 May 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
5 Sept - 8 Sept
found 17 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (1,016 reviews)
Best place to stay in boston

Reviewed on 2 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 £270 per night from 24 Aug to 25 Aug
£270
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Very nice place and great location."

Reviewed on 1 Aug 2025

Harbor Hotel Provincetown
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 £192 per night from 1 Sept to 2 Sept
£192
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Wonderful property...good rooms with incredible water views."

Reviewed on 30 Jul 2025

The Provincetown Inn
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

2 out of 5
352 Main Street, Dennis Port, MA
Fully refundableReserve now, pay when you stay
The price is £92 per night from 1 Sept to 2 Sept
£92
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (886 reviews)
"It was fine"

Reviewed on 31 Jul 2025

Holiday Hill Inn & Suites
See all 4,346 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Pleasant Point travel package cost?
We make it easy for everyone to travel, with Pleasant Point travel packages starting from as little as £990. You'll have the flexibility to bundle your favourite hotels, airlines and car rental. For the ultimate getaway, why not add some tours and activities to your travel itinerary?
If I'm not able to travel, can I cancel my Pleasant Point travel package?
Your situation can change without warning, so yes. You may be able to cancel or amend your Pleasant Point travel package for free if you've booked in the last 24 hours. For bookings older than that, you can still cancel and rebook, but your hotel, car rental company or airline may impose a fee. Want more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Pleasant Point?
Track down flights that fit your busy schedule, add a hotel to your booking and watch the savings rack up with a Pleasant Point travel package. It's as easy as that! From hotels and flights to rental cars and activities, Expedia makes travelling on a budget easy. And with over 550 airlines and 1,000,000 properties all over the world to choose from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later Pleasant Point holidays?
Expedia has partnered with online lender Klarna to make your next trip easier on the purse strings. Paying in instalments means you can spread the costs of your next adventure, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Consider these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all budgets, so you can lock in that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip over multiple transactions.
  • Low deposit holidays: When you stumble on an unbeatable deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Pleasant Point?
With lots to discover in Pleasant Point, it'd be handy for you to book a hotel near its attractions. Wellfleet Preservation Hall, Wellfleet Harbour Actors Theatre and Wellfleet Public Library are some good ones to add to your to-do list.
What are the top hotels in Pleasant Point?
If this will be your first time in Pleasant Point, book a room at Wellfleet Motel and Lodge or Endless Coast, A Boutique Hotel. Both offer friendly service and are favourites among many travellers.
How far in advance should I book my Pleasant Point holiday?
While prices do change, we generally suggest booking your spot as soon as possible. Many international airfares become available on Expedia up to 12 months in advance. If circumstances have left you booking late, you might still be lucky. Cheap tickets to Pleasant Point sometimes appear only weeks before departure.
What does an Expedia Pleasant Point travel package include?
Expedia has everything you need to arrange your Pleasant Point escape, but what your package looks like is up to you. Pick from any combination of flights, hotels and rental cars. After some experiences or tours to keep you on the go? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a package deal to match your needs.
What should I know before booking a Pleasant Point travel package?
When you book your hotels, flights and car rentals together, you'll enjoy great discounts. Whether you're planning a rural escape in a cottage or would rather stay in a ritzy city hotel, Expedia can help make it happen.
Can I choose my airline with a Pleasant Point Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.

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
Mayo Beach

Mayo Beach

If a restful holiday is part of your travel plans, Mayo Beach might be the perfect place to visit during your trip to Wellfleet. Discover the area's seafood restaurants or seek out the hiking trails.

Mayo Beach

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.