Pleasant Point Holidays from £1,268

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was £2,024, price is now £1,268 per person
£1,268
per person
20 Jul - 27 Jul
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
Good for the price. Friendly staff.

Reviewed on 15 May 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £3,773, price is now £1,970 per person
£1,970
per person
20 Jul - 27 Jul
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
clean and great staff

Reviewed on 8 May 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was £2,703, price is now £1,516 per person
£1,516
per person
20 Jul - 27 Jul
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
8.6/10 Excellent! (406 reviews)
1st time, felt safe. Towels were available. Bring your own lock. 1 block from train station. And good food and stores nearby

Reviewed on 15 May 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was £2,540, price is now £1,735 per person
£1,735
per person
20 Jul - 27 Jul
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
8.8/10 Excellent! (1,475 reviews)
Staff on the front desk were absolutely fantastic! The hotel location perfect especially for the TD Gardens. Breakfast is available but we only had once. Shame the bar area wasn't open. Overall, a fantastic hotel that we would highly recommend if you are coming to Boston. Also, super close to the airport making transfers easy.

Reviewed on 13 May 2026

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
North Brookline
Save 100% on your flight
Price was £2,202, price is now £1,516 per person
£1,516
per person
9 Jul - 16 Jul
found 16 hours ago
Return direct flight included
London (LON) to Boston (BOS)
7.4/10 Good! (3 reviews)
Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities.

Reviewed on 1 Apr 2026

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 £134 per night from 8 Jun to 9 Jun
£134
per night
8 Jun - 9 Jun
8.2/10 Very Good! (1,000 reviews)
The second floor, ocean-view suite is worth the extra money! Rooms are neat as a pin, and the gentleman who has checked us in every time we have stayed is simply delightful! Rooms and lobby decor have a mid-century modern vibe, and if you get a suite, you will have 2 huge bathrooms! I cannot rave ...

Reviewed on 12 May 2026

Harbor Hotel Provincetown
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is £482 per night from 21 May to 22 May
£482
per night
21 May - 22 May
9.2/10 Wonderful! (826 reviews)
window and door were not closing all the way, got noise complaint after daughter became ill. Food was good staff ok

Reviewed on 13 May 2026

Chatham Bars Inn
Dune Crest Hotel

Dune Crest Hotel

2.5 out of 5
535 Route 6 North Truro MA
Fully refundableReserve now, pay when you stay
The price is £67 per night from 21 May to 22 May
£67
per night
21 May - 22 May
8.8/10 Excellent! (1,000 reviews)
The room was very clean the location was exactly where we wanted not in the middle of anything but very close to all the places we wanted to go. The property is a little dated but kinda in a weird way adds to the charm

Reviewed on 30 Dec 2025

Dune Crest Hotel
See all 4,276 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 £1,268. 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

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.