Upton Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Upton Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
HomeAwhile
$740
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
Book a stay at this business-friendly hotel in Scarborough. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Maine Mall and Thompson's Point are located nearby.
Space and facilities
Reviewed on Sep 16, 2026
Boston Harbor Hotel
North End
$2,523
per person
Oct 22 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
Hotel and staff were excellent. The SeaGrill waitstaff was especially friendly and accommodating
Reviewed on Sep 15, 2026
Fairmont Copley Plaza, Boston
Back Bay
$1,878
per person
Oct 22 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Newbury Boston
Back Bay
$2,691
per person
Oct 22 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Eurostars The Boxer
West End
$1,899
per person
Oct 22 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Holiday Inn Express & Suites Boston - Cambridge by IHG
East Cambridge
$1,216
per person
Oct 22 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Top Hotel Deals
Sonesta Select Boston Foxborough Mansfield
35 Foxborough Boulevard Foxborough MA
Book a stay at this business-friendly hotel in Foxborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd Framingham MA
Stay at this motel in Framingham. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Extended Stay America Suites Boston Westborough Computer Dr
1800 Computer Dr Westborough MA
Book a stay at this business-friendly hotel in Westborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
enVision Hotel & Conference Center Mansfield-Foxboro
31 Hampshire St Mansfield MA
Book a stay at this business-friendly hotel in Mansfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Bally's Twin River Lincoln Casino & Hotel
100 Twin River Rd Lincoln RI
Stay at this hotel in Lincoln. Enjoy free WiFi, free valet parking, and 17 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
La Quinta Inn by Wyndham Auburn Worcester
446 Southbridge St Auburn MA
Book a stay at this business-friendly hotel in Auburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
The Verve Hotel Boston Natick, Tapestry Collection by Hilton
1360 Worcester St Natick MA
Book a stay at this business-friendly hotel in Natick. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Courtyard by Marriott Boston Natick
342 Speen St Natick MA
Book a stay at this business-friendly hotel in Natick. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Sonesta Select Boston Milford
10 Fortune Blvd Milford MA
Book a stay at this business-friendly hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Courtyard by Marriott Boston Marlborough
75 Felton St Marlborough MA
Book a stay at this business-friendly hotel in Marlborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
DoubleTree by Hilton Hotel Boston - Westborough
5400 Computer Dr Westborough MA
Book a stay at this business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hampton Inn & Suites North Attleboro
55 Draper Avenue North Attleboro MA
Book a stay at this business-friendly hotel in North Attleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western The Inn at Sharon/Foxboro
395 Old Post Rd Sharon MA
Book a stay at this business-friendly hotel in Sharon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn Boston Natick
319 Speen St Natick MA
Book a stay at this business-friendly hotel in Natick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
All Seasons Inn & Suites Smithfield Providence
355 George Washington Hwy Smithfield RI
Book a stay at this business-friendly hotel in Smithfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bally's Lincoln and Rustic ...
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.
Tue, Nov 3 - Tue, Nov 10
LAX
Los Angeles Intl.
BOS
Logan Intl.
$258
Roundtrip
found 1 day ago
Tue, Oct 20 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$308
Roundtrip
found 1 day ago
Tue, Nov 10 - Tue, Nov 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$337
Roundtrip
found 3 days ago
Wed, Dec 2 - Sat, Dec 12
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 1 day ago
Thu, Nov 5 - Mon, Nov 9
LAX
Los Angeles Intl.
BOS
Logan Intl.
$377
Roundtrip
found 16 hours ago
Best points of interest in Upton
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