Pleasant Point Holidays from £858

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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.
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
Save 100% on your flight
Price was £1,404, price is now £858 per person
£858
per person
17 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LGW) to Provincetown (PVC)
8.2/10 Very good! (1,007 reviews)
Great stay

Reviewed on 12 Jul 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £3,065, price is now £1,781 per person
£1,781
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LHR) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on 11 Jul 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was £2,097, price is now £1,246 per person
£1,246
per person
16 Sept - 23 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
We loved the Atlas Hotel, located directly opposite Harvard on a quiet street in Boston. It is a beautifully appointed hotel with good-sized rooms (we took a corner room and were very happy with it), and it is well-suited to international travellers (space for bags, etc). The bed is comfortable, and the rooms are well serviced and clean throughout our stay, with lovely linens, towels, etc. We did have a good hairdryer, essential for me (long hair) and a steamer. We did ask for an iron and ironing board. The iron was super, but the ironing board had seen better days! This was mentioned and replaced quickly. What makes this hotel are the staff; they are friendly, always say hello, and ask if they can help, which made it a pleasure to be here and stay here. This was in the middle of the World Cup, so I can imagine they were busy with many travellers arriving and leaving. We liked the tasty breakfasts and the great cocktails on the top floor of the hotel, which has a good view over the Boston environs. I would be delighted to stay here again in the future. A special place where you feel special for being here.

Reviewed on 10 Jul 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was £2,426, price is now £1,499 per person
£1,499
per person
27 Sept - 4 Oct
found 9 hours ago
Return flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (258 reviews)
Lovely property near the downtown and Concord.

Reviewed on 10 Jul 2026

Crowne Pointe Historic Inn & Spa - Adults Only

Crowne Pointe Historic Inn & Spa - Adults Only

4 out of 5
Save 100% on your flight
Price was £1,976, price is now £1,251 per person
£1,251
per person
17 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LGW) to Provincetown (PVC)
9.2/10 Wonderful! (888 reviews)
Everything about the property was great! Staff was very accommodating when the AC didn’t work in our room and came to fix it

Reviewed on 12 Jul 2026

Top hotels in Pleasant Point

Dune Crest Hotel

Dune Crest Hotel

2.5 out of 5
535 Route 6 North Truro MA
The price is £255 per night from 9 Aug to 10 Aug
£255
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (1,026 reviews)
"The newly renovated rooms are amazing looking now. And they did an awesome job improving the grounds."

Reviewed on 12 Jul 2026

Dune Crest Hotel
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 £275 per night from 3 Aug to 4 Aug
£275
3 Aug - 4 Aug
includes taxes & fees
8/10 Very good! (1,017 reviews)
"Nice setting away from busy main areas and not far to walk. Hotel improvement works seem to be ongoing to modernise with new breakfast cafe opened and rooms looking more modern. Staff were friendly."

Reviewed on 10 Jul 2026

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 £130 per night from 3 Aug to 4 Aug
£130
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
"Staff was very friendly and helpful. The pictures that were listed when booking did not portray the rooms. Beds were booked as (2) queens but they were fulls. Carpets needs to be cleaned my suns socks were super dirty after walking on the floor. The overall listing is a little misleading for arcade ..."

Reviewed on 12 Jul 2026

Holiday Hill Inn & Suites
See all 4,377 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.
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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 £858. 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.

Things to do

Cape Cod and Provincetown Scenic Self-Guided Driving Audio Tour

Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour

£19
per traveller
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

£34
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

£38
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Wellfleet

* 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.