Title: Pleasant Point Vacation Packages 2026 from $500 | Expedia.com

[Hotels in Pleasant Point](https://expedia.com/Pleasant-Point-Wellfleet-Hotels.0-n553248635976481213-0.Travel-Guide-Filter-Hotels)[Flights to Wellfleet](https://expedia.com/Cheap-Flights-To-Wellfleet.d6050694.Travel-Guide-Flights)[Car Rentals in Pleasant Point](https://expedia.com/Car-Rentals-In-Pleasant-Point.d553248635976481213.Car-Rental-Guide)

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# Pleasant Point Vacations from $500

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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Better together  
Save up to $1,045 when you book a flight and hotel together\*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Plan, book, and manage your trip all in one place

## Your Pleasant Point Vacation

With a personalized vacation package to Pleasant Point, you'll spend less time planning and more time uncovering this sought-after neighborhood. From its nature to its views, there's plenty to discover here. Hoping to see the sights during your trip to Pleasant Point? Don't miss nearby attractions such as [Marconi Beach](https://www.expedia.com/Marconi-Beach-Massachusetts.d6287508.Vacation-Attraction), [Cahoon Hollow Beach](https://www.expedia.com/Cahoon-Hollow-Beach-Massachusetts.d6070151.Vacation-Attraction) and [Indian Neck Beach](https://www.expedia.com/Indian-Neck-Beach-Wellfleet.d6070183.Vacation-Attraction). Stop daydreaming and start doing. When it's time to book your vacation to Pleasant Point, Expedia will help get you there.

## The Latest Pleasant Point Vacation Packages

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

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### D. Hotel Suites & Spa

Save 100% on your flight

$500

per person

Apr 21 - Apr 28

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

9.4/10 Exceptional! (2,242 reviews)

There were many good things about the stay however; our room was super close to the interstate and the traffic and trucks starting rolling by at 5:30 am. I searched for earplugs and it was not conducive to easy sleep. I would not stay again unless the room was far away from the highway. Be forewarned. The people were super nice and the room was fine. Not great sleep was not!

Reviewed on Feb 27, 2026

![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Boston

Downtown Boston

Save 100% on your flight

$923

per person

May 9 - May 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.6/10 Exceptional! (1,004 reviews)

Friendly staff, clean room

Reviewed on Feb 20, 2026

![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Boston Park Plaza

Bay Village

Save 100% on your flight

$891

per person

May 24 - May 30

found 4 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8.4/10 Very Good! (3,135 reviews)

Very friendly and helpful staff. Terrific location. Clean and comfortable rooms. Highly recommend!

Reviewed on Mar 1, 2026

![The Colonnade Hotel Back Bay](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/f43e7537_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Colonnade Hotel Back Bay

Back Bay

Save 100% on your flight

$640

per person

May 15 - May 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.2/10 Wonderful! (2,268 reviews)

We stay at the Colonnade fairly regularly because of its convenient location and easy parking. This time we were stuck there because of a blizzard, so we spent more time actually hanging around the hotel. The lobby is really comfortable and cozy with a gas fire and a front wall of glass. The room was also very comfortable, including beds, pillows, bathrobes. We ate breakfast twice at the hotel restaurant and the staff were warm and friendly.

Reviewed on Feb 25, 2026

![Found Hotel Boston Common](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/8f309a43_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Found Hotel Boston Common

Bay Village

Save 100% on your flight

$923

per person

Apr 3 - Apr 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8.2/10 Very Good! (1,253 reviews)

Great location by Boston common garden. Loved it.

Reviewed on Feb 28, 2026

## Pleasant Point Hotel Deals

![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chatham Bars Inn

297 Shore Rd Chatham MA

$364 nightly

$417 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=19139&PinnedHotelID=19139&HadPinnedHotel=true&regionId=553248635976481213)

![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chatham Wayside Inn

512 Main St Chatham MA

Fully refundableReserve now, pay when you stay

$148 nightly

$169 total

Mar 4 - Mar 5

Total with taxes and fees

9.2/10 Wonderful! (635 reviews)

Friendly staff, clean and spacious room, convenience of having a restaurant on site, and convenience of walking to all the stores and restaurants.

Reviewed on Feb 16, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=1517204&PinnedHotelID=1517204&HadPinnedHotel=true&regionId=553248635976481213)

![Modern Beachfront Condo, Gorgeous Views and Centrally Located](https://images.trvl-media.com/lodging/61000000/60390000/60385500/60385476/5e8570d8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Modern Beachfront Condo, Gorgeous Views and Centrally Located

 Provincetown MA

10/10 Exceptional! (61 reviews)

Our second time staying at this beautiful condo right on the water in Provincetown. We can't wait to go back again!! The view is spectacular, the condo warm and inviting, very comfortable and impeccably clean. Our host John was again very helpful, and easy to get in touch with.

Reviewed on Feb 22, 2026

[Get rates](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=60385476&PinnedHotelID=60385476&HadPinnedHotel=true&regionId=553248635976481213)

[](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=60385476&PinnedHotelID=60385476&HadPinnedHotel=true&regionId=553248635976481213)

[See all 4,166 properties in Pleasant Point](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&regionId=553248635976481213)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

### Discover the most popular places to visit in Pleasant Point

![New stairs at Marconi Beach](https://images.trvl-media.com/place/6050694/ecc45920-7d7a-47d0-a9eb-370a78c3d50b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Marconi Beach

Why not spend a carefree afternoon at Marconi Beach during your travels in Wellfleet? Discover the area's seafood restaurants or seek out the hiking trails. 

[](https://expedia.com/Marconi-Beach-Wellfleet.d6287508.Vacation-Attraction)

![Cahoon Hollow Beach](https://images.trvl-media.com/place/6070151/9717a237-72eb-46b0-be02-473d8ad18097.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Cahoon Hollow Beach

Enjoy a relaxing day at the beach and a lively night at the bar at this favorite daytrip destination.

[](https://expedia.com/Cahoon-Hollow-Beach-Wellfleet.d6070151.Vacation-Attraction)

![Sand Dunes, Marconi Beach, Cape Cod National Seashore, Wellfleet](https://images.trvl-media.com/place/6070183/e301d3e7-77b9-42e7-acac-251307be2a60.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Beach

Why not spend a carefree afternoon at Beach during your travels in Wellfleet? Discover the area's seafood restaurants or seek out the hiking trails. 

[](https://expedia.com/Beach-Wellfleet.d6070183.Vacation-Attraction)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.