
Gorham Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Gorham Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Encore Boston Harbor
$1,081
per person
Nov 15 - Nov 19
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this 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.

Boston Harbor Hotel
North End
$1,373
per person
Nov 15 - Nov 19
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Everything about this hotel is wonderful! We would definitely stay here again.
Reviewed on Sep 8, 2026

Raffles Boston
Back Bay
$1,281
per person
Nov 15 - Nov 19
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Mandarin Oriental, Boston
Back Bay
$1,517
per person
Nov 15 - Nov 19
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Great hotel in great location.
Staff earned five star status.
Reviewed on Sep 6, 2026

The Langham, Boston
Downtown Boston
$1,208
per person
Nov 15 - Nov 19
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
We loved it.
Reviewed on Sep 7, 2026

The Colonnade Hotel Back Bay
Back Bay
$1,459
per person
Oct 21 - Oct 25
found 7 hours ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
We had a wonderful stay at this hotel! The staff was friendly and welcoming, and there was always someone at the door ready to greet us and help whenever needed.
We stayed for a week and really appreciated that our room was cleaned every day. It seems like many hotels no longer provide daily housekeeping unless you specifically request it, so this was a really nice touch. The room was very comfortable, and we felt right at home throughout our stay.
The location was fantastic. The subway station was right on the corner, which made it incredibly convenient to get everywhere we wanted to go. Fenway Park was only a 20-minute walk away, and we loved exploring Newbury Street, with all of its great shopping and restaurants.
We would definitely recommend this hotel, especially for its comfort, friendly staff, and excellent location. We would happily stay here again!
Reviewed on Sep 8, 2026
Top Hotel Deals

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

Quality Inn & Suites South Portland
738 Main Street South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...

Portland Harbor Hotel
468 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...

Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...

Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...

Fireside Inn & Suites Portland
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...

Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...

The Westin Portland Harborview
157 High St Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...

Embassy Suites by Hilton Portland Maine
1050 Westbrook Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...

Waves Oceanfront Resort
87 W Grand Ave Old Orchard Beach ME
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...

Spark by Hilton Portland Airport Maine Mall
461 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...

Portland Regency Hotel & Spa
20 Milk Street Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
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.

Wed, Sep 30 - Wed, Oct 7
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$218
Roundtrip
found 2 days ago

Tue, Oct 13 - Thu, Oct 22
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$237
Roundtrip
found 4 hours ago

Wed, Dec 2 - Sat, Dec 12
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$257
Roundtrip
found 3 days ago

Sat, Sep 26 - Wed, Sep 30
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267
Roundtrip
found 3 days ago

Wed, Sep 30 - Wed, Oct 7
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$277
Roundtrip
found 2 days ago
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