Holliston Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Holliston Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Bostonian Boston
Government Center
Price was $1,029, price is now $817 per person
$817
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.
The Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was $1,763, price is now $1,250 per person
$1,250
per person
Nov 23 - Nov 29
found 8 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Porter Square Hotel
Porter Square
Price was $1,142, price is now $843 per person
$843
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 $1,131, price is now $880 per person
$880
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.
Hotel AKA Back Bay
Back Bay
Price was $1,248, price is now $985 per person
$985
per person
Nov 23 - Nov 29
found 8 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Hotel Commonwealth
Fenway–Kenmore
Price was $1,145, price is now $915 per person
$915
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
citizenM Boston Back Bay
408 Newbury street, Boston, MA
32.45 km from city center
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...
Copley Square Hotel, a FOUND Hotel
47 Huntington Ave, Boston, MA
33.16 km from city center
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the ...
The Arcadian Hotel
1200 Beacon St, Brookline, MA
30.36 km from city center
Stay at this 3.5-star hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff ...
The Westin Copley Place, Boston, a Marriott Hotel
10 Huntington Ave, Boston, MA
33.26 km from city center
Stay at this 4-star eco-certified hotel in Boston. Enjoy 4 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Boston Marriott Copley Place
110 Huntington Ave, Boston, MA
33.04 km from city center
Stay at this 4-star business-friendly hotel in Boston. Enjoy 3 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Sheraton Boston, a Marriott Hotel
39 Dalton St, Boston, MA
32.63 km from city center
Book a stay at this eco-certified hotel in Boston. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...
Hyatt Place Boston/Braintree
50 Forbes Road, Braintree, MA
31.92 km from city center
Stay at this 3.5-star business-friendly hotel in Braintree. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Midtown Hotel
220 Huntington Avenue, Boston, MA
32.53 km from city center
Stay at this hotel in Boston. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Copley Square and Fenway Park are located ...
The Lenox Hotel Boston
61 Exeter Street, Boston, MA
33.17 km from city center
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Hampton Inn & Suites Boston Crosstown Center
811 Massachusetts Ave, Boston, MA
32.63 km from city center
Stay at this 3-star hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
Embassy Suites by Hilton Boston Waltham
550 Winter Street, Waltham, MA
26.55 km from city center
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, a 24-hour fitness center, and WiFi (surcharge). Our guests praise the breakfast ...
The Charles Hotel
One Bennett Street, Cambridge, MA
31.87 km from city center
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 ...
Ramada by Wyndham Boston
800 Morrissey Blvd, Boston, MA
32.68 km from city center
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
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 19 hours ago
$197
Roundtrip
found 19 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$218 Roundtrip, found 19 hours ago
$218
Roundtrip
found 19 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$298 Roundtrip, found 19 hours ago
$298
Roundtrip
found 19 hours ago
Wed, Nov 12 - Sun, Nov 16
PDX
Portland Intl.
BOS
Logan Intl.
$506 Roundtrip, found 19 hours ago
$506
Roundtrip
found 19 hours ago