Pleasant Point Holidays from £1,005

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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.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Price was £1,414, price is now £1,005 per person
£1,005
per person
30 Apr - 7 May
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9/10 Wonderful! (2,215 reviews)
Wonderful, helpful management, a nice vibe at the bar, and a comfy, pleasant room.

Reviewed on 8 Feb 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was £4,383, price is now £2,297 per person
£2,297
per person
1 May - 8 May
found 22 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on 25 Jan 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 £2,086, price is now £1,310 per person
£1,310
per person
1 May - 8 May
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on 21 Oct 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £4,102, price is now £2,875 per person
£2,875
per person
30 Apr - 7 May
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Attention to guest needs.

Reviewed on 8 Feb 2026

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Price was £1,536, price is now £1,084 per person
£1,084
per person
1 May - 8 May
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
6.8/10 (173 reviews)
The room is clean and the furniture is pretty, but since it's part of an apartment complex, you don't have immediate help with extra sheets or heater support; so first two days out 4, we had to deal with the cold of the room. Third and 4th, since we had called for help, they did left the extra sheets and fixed the thermostat.

Reviewed on 6 Dec 2025

Top hotels in Pleasant Point

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is £306 per night from 11 Feb to 12 Feb
£306
11 Feb - 12 Feb
includes taxes & fees
9.2/10 Wonderful! (808 reviews)
Beautiful property

Reviewed on 24 Jan 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (630 reviews)
Courteous staff, helpful with dining suggestions. Loved the room. Very comfortable bed, warm and cozy.

Reviewed on 29 Jan 2026

Get rates
Chatham Wayside Inn
Modern Beachfront Condo, Gorgeous Views and Centrally Located

Modern Beachfront Condo, Gorgeous Views and Centrally Located

Provincetown MA
9.8/10 Exceptional! (60 reviews)
It was a great view, though we had a good look at a sauna/polar plunge group every day, hosted by a local yoga studio, that operated right behind our harborside window. Parking is a 5 minute walk away, but it is a very walkable area and you can do many things without driving anywhere. The flat is ...

Reviewed on 29 Dec 2025

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Modern Beachfront Condo, Gorgeous Views and Centrally Located
See all 4,166 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 £1,005. 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.