Pleasant Point Vacations from $532

Book a Hotel + Flight or Car together to unlock savings

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, Cahoon Hollow Beach and Indian Neck Beach. 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.
Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport

2.5 out of 5
Save 100% on your flight
Price was $768, price is now $532 per person
$532
per person
Jan 25 - Feb 1
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (2,178 reviews)
No bathtub. Parking fee. Extra fee for security that is not stated

Reviewed on Dec 8, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,256, price is now $566 per person
$566
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,656, price is now $1,003 per person
$1,003
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,025, price is now $689 per person
$689
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Everything was great. Everyone was unusually helpful and cheerful. Room was lovely and very clean. Location perfect.

Reviewed on Dec 4, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,412, price is now $972 per person
$972
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Excellent hotel in all aspects. Comfortable and spacious rooms and attentive staff. Only exception is $70 valet parking which is way over priced (even for Boston) especially on a weekend evening.

Reviewed on Dec 7, 2025

Pleasant Point Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
$357 nightly
The price is $409 total per night from Dec 14 to Dec 15
$409 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (796 reviews)
Great accommodation and staff.

Reviewed on Nov 8, 2025

Chatham Bars Inn
Modern Beachfront Condo, Gorgeous Views and Centrally Located

Modern Beachfront Condo, Gorgeous Views and Centrally Located

Provincetown MA
9.8/10 Exceptional! (57 reviews)
We loved our stay in this condo. It is beautifully designed with a fantastic kitchen. The view is stunning and you are right in the middle of everything. Parking could be a problem during the busy season since there isn’t any directly in front of the condo. Thankfully this wasn’t an issue for us. ...

Reviewed on Dec 2, 2025

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

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $245 total per night from Dec 22 to Dec 23
$245 total
Dec 22 - Dec 23
Total with taxes and fees
9.2/10 Wonderful! (598 reviews)
Loved it. Will be back.

Reviewed on Dec 3, 2025

Chatham Wayside Inn
See all 4,174 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Pleasant Point

New stairs at Marconi Beach

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.

Marconi Beach
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
Beach

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.

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