Search Deals onSouth Portland Vacation Packages
South Portland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Beverly
Save 100% on your flight
per person
May 9 - May 14
found 10 hours ago
Roundtrip flight included
Richmond (RIC) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Beverly. Enjoy free WiFi, free parking, and an in-room coffeemaker. Our guests praise the clean rooms in our reviews. Popular attractions Salem Witch Museum and Dogs by Design & Cats Too are located nearby.
The Charles Hotel
Save 100% on your flight
per person
May 9 - May 14
found 10 hours ago
Roundtrip flight included
Richmond (RIC) to Boston (BOS)
Stay at this 4-star luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Staypineapple, A Delightful Hotel, South End
Save 100% on your flight
per person
May 9 - May 14
found 10 hours ago
Roundtrip flight included
Richmond (RIC) to Boston (BOS)
Stay at this 3-star boutique hotel in Boston. Enjoy free bicycles on site, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Beacon Hill Hotel
Save 100% on your flight
per person
Jun 9 - Jun 13
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Cove At Salem
per person
Jun 9 - Jun 13
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Boston (BOS)
Stay at this 3-star hotel in Salem. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.
Life House, Nantucket
Save 100% on your flight
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Boston (BOS)
Stay at this 3.5-star hotel in Nantucket. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions First Congregational Church and Jethro Coffin House are located nearby.
citizenM Boston North Station
Save 100% on your flight
per person
Jun 9 - Jun 13
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
The Royal Sonesta Boston
Save 100% on your flight
per person
Jun 9 - Jun 13
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
South Portland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
South Portland Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Apr 18 - Thu, May 1
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Tue, May 6 - Tue, May 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Tue, Jun 3 - Fri, Jun 6
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$193 Roundtrip, found 6 days ago
$193
Roundtrip
found 6 days ago
Tue, Jun 17 - Wed, Jun 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Maine Mall Vacations
- Willard Beach Vacations
- Southern Maine Community College Vacations
- Bug Light Vacations
- Sable Oaks Golf Course Vacations
- Lyric Music Theater Vacations
- Maine Military Museum Vacations
- Fort Preble Vacations
- South Portland Historical Society Museum Vacations
- Old Orchard Beach Pier Vacations
- Thompson's Point Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in South Portland
- Car rentals in Portland
- Car rentals in Old Orchard Beach
- Car rentals in Kennebunkport
- Car rentals in Kennebunk
- Car rentals in Scarborough
- Car rentals in Freeport
- Car rentals in Cape Elizabeth
- Car rentals in Saco
- Car rentals in Biddeford
- Car rentals in Brunswick
- Car rentals in Raymond
- Car rentals in Ocean Park
Book your South Portland Vacation
Prices are always lower in the app!
Book and go: Last-minute deals and trip details all in one place
Exclusive prices: Hot Rate® Hotels always cost less in the app
Fresh features: So slick you’ll never go back to desktop
