Sterling Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sterling Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Price was $853, price is now $671 per person
$671
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), 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 Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $2,048, price is now $1,381 per person
$1,381
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Porter Square Hotel
Porter Square
Price was $1,060, price is now $761 per person
$761
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Cambridge. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Encore Boston Harbor are located nearby.
Revere Hotel Boston Common
Bay Village
Price was $1,037, price is now $787 per person
$787
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the bar in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Bostonian Boston
Government Center
Price was $933, price is now $723 per person
$723
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, room service, and a health club. 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.
Hotel Commonwealth
Fenway–Kenmore
Price was $1,051, price is now $821 per person
$821
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
Top Hotel Deals
Chocksett Inn and Restaurant
59 Laurelwood Road, Sterling, MA
1.82 km from city center
Stay at this 3.5-star hotel in Sterling. Enjoy free WiFi, free parking, and room service. Popular attractions Mary Had a Little Lamb Statue and Davis' Farmland ...
Inn at Historic Concord
740 Elm St, Concord, MA
30.75 km from city center
Stay at this 3-star hotel in Concord. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Discovery Museums and Minute Man National Historic ...
DoubleTree by Hilton Hotel Boston - Westborough
5400 Computer Dr, Westborough, MA
22.62 km from city center
Stay at this 4-star business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Colonial Hotel
625 Betty Spring Road, Gardner, MA
21.06 km from city center
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
The Verve Hotel Boston Natick, Tapestry Collection by Hilton
1360 Worcester St, Natick, MA
34.25 km from city center
Stay at this 3.5-star business-friendly hotel in Natick. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean ...
Motel 6 Framingham, MA - Boston West
1668 Worcester Rd, Framingham, MA
27.73 km from city center
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. ...
Courtyard by Marriott Boston Natick
342 Speen St, Natick, MA
34.27 km from city center
Stay at this 3-star business-friendly hotel in Natick. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Monticello Inn Framingham
90 Worcester Rd, Framingham, MA
33.69 km from city center
Stay at this motel in Framingham. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Fun and Games Family Entertainment Center and ...
Red Roof Inn PLUS+ Boston - Framingham
650 Cochituate Rd, Framingham, MA
33.95 km from city center
Stay at this hotel 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. ...
Best Western Royal Plaza Hotel & Trade Center
181 Boston Post Rd W, Marlborough, MA
17.52 km from city center
Book a stay at this business-friendly hotel in Marlborough. Enjoy free breakfast, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
The Minuteman Inn
71 Hosmer St, Acton, MA
27.59 km from city center
Book a stay at this business-friendly motel in Acton. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Jam Time and Maynard Outdoor ...
Aloft Framingham
130 Worcester Road, Framingham, MA
33.55 km from city center
Stay at this 3-star business-friendly hotel in Framingham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
AVIA Residences on Research - Extended Stay
25 Connector Road, Westborough, MA
22.13 km from city center
Stay at this 3-star business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise 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, Nov 13 - Sat, Nov 15
PDX
Portland Intl.
BOS
Logan Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$218 Roundtrip, found 2 hours ago
$218
Roundtrip
found 2 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$298 Roundtrip, found 2 hours ago
$298
Roundtrip
found 2 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$506 Roundtrip, found 2 hours ago
$506
Roundtrip
found 2 hours ago