Pleasant Point Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Pleasant Point Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham West Yarmouth/Hyannis Cape Cod Area
Save 100% on your flight
per person
Aug 1 - Aug 6
found 9 hours ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
Book a stay at this golf hotel in West Yarmouth. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Cape Cod Inflatable Park are located nearby.
Holly Tree Resort
Save 100% on your flight
per person
Aug 1 - Aug 6
found 9 hours ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
Stay at this 3-star aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor are located nearby.
YOTEL Boston
Seaport District
Save 100% on your flight
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
Encore Boston Harbor
Save 100% on your flight
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Hotel AKA Back Bay
Back Bay
Save 100% on your flight
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Whitney Hotel
Beacon Hill
Save 100% on your flight
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
Don't see what you're looking for?
See all available trips from Columbus to Pleasant Point
View all tripsTop Hotel Deals
The Provincetown Inn
1 Commercial Street, Provincetown, MA
21.2 km from Pleasant Point
Stay at this 3-star beach hotel in Provincetown. Enjoy an outdoor pool, 3 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in ...
Harbor Hotel Provincetown
698 Commercial St, Provincetown, MA
21.2 km from Pleasant Point
Book a stay at this beach hotel in Provincetown. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the pool and the helpful staff in ...
Chatham Bars Inn
297 Shore Rd, Chatham, MA
25.57 km from Pleasant Point
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
The Corsair & Cross Rip Oceanfront Resort
41 Chase Ave, Dennis Port, MA
30.08 km from Pleasant Point
Book a stay at this beach hotel in Dennis Port. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions West Dennis Beach and Sea Street Beach ...
Surfside Hotel and Suites
543 Commercial Street, Provincetown, MA
21.56 km from Pleasant Point
Book a stay at this beach hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
The Villages at Ocean Edge
One Villages Drive, Brewster, MA
16.6 km from Pleasant Point
Stay at this 3.5-star beach resort in Brewster. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Cape Colony Inn
280 Bradford Street, Provincetown, MA
21.71 km from Pleasant Point
Stay at this hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Chatham Tides
394 Pleasant St, PO Box 215, South Chatham, MA
27.13 km from Pleasant Point
Book a stay at this beach motel in South Chatham. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
Sandcastle Resort and Club
929 Commercial Street, Provincetown, MA
20.64 km from Pleasant Point
Stay at this 3-star beach aparthotel in Provincetown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Breakwater Hotel
716 Commercial St, Provincetown, MA
21.16 km from Pleasant Point
Book a stay at this beach motel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Chatham Wayside Inn
512 Main St, Chatham, MA
26 km from Pleasant Point
Stay at this 4-star golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Wequassett Resort and Golf Club
2173 Head of the Bay Road, Route 28, Harwich, MA
21.03 km from Pleasant Point
Stay at this 5-star luxury resort in Harwich. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Captain's Cove Golf Course and Captains ...
Dune Crest Hotel
535 Route 6, North Truro, MA
17.63 km from Pleasant Point
Stay at this hotel in North Truro. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Aug 21 - Wed, Aug 27
LAX
Los Angeles Intl.
BOS
Logan Intl.
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Tue, Aug 26 - Sun, Aug 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Mon, Sep 1 - Sat, Sep 6
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Mon, Sep 1 - Sat, Sep 6
PDX
Portland Intl.
HYA
Barnstable Municipal
$506 Roundtrip, found 6 days ago
$506
Roundtrip
found 6 days ago
Best points of interest in Wellfleet
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations