Litchfield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Litchfield 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 15 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 15 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
Methuen Inn and Conference Center
159 Pelham Street, Methuen, MA
24.05 km from city center
Stay at this hotel in Methuen. Enjoy free WiFi, free parking, and room service. Popular attractions Canobie Lake Park and Methuen Memorial Music Hall are located ...
DoubleTree by Hilton Manchester Downtown
700 Elm St., Manchester, NH
16.55 km from city center
Stay at this 4-star hotel in Manchester. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Express Chelmsford by IHG
8 Independence Drive, Chelmsford, MA
27.77 km from city center
Book a stay at this business-friendly hotel in Chelmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Boston - Andover
123 Old River Rd, Andover, MA
25.98 km from city center
Stay at this 4-star business-friendly hotel in Andover. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Park View Inn - Salem
109 S Broadway, Salem, NH
20.86 km from city center
Stay at this motel in Salem. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Chateau Merrimack Resort & Spa
160 Pawtucket Blvd, Tyngsboro, MA
20.8 km from city center
Stay at this 4.5-star luxury hotel in Tyngsboro. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Tru by Hilton Manchester Downtown
135 Spring Street, Manchester, NH
17.11 km from city center
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Hilton Garden Inn Tewksbury Andover
4 Highwood Drive, Tewksbury, MA
28.42 km from city center
Stay at this 3-star business-friendly hotel in Tewksbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr, Salem, NH
18.88 km from city center
Stay at this 3-star business-friendly hotel in Salem. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd, Andover, MA
26.3 km from city center
Stay at this 3-star business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Best Western Plus Executive Court Inn & Conference Center
13500 S Willow St, Manchester, NH
11.51 km from city center
Stay at this 3-star business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
EVEN Hotels Manchester Airport by IHG
55 John E. Devine Drive, Manchester, NH
13.4 km from city center
Stay at this 3.5-star business-friendly hotel in Manchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Sonesta Select Boston Lowell Chelmsford
30 Industrial Ave East, Lowell, MA
27.5 km from city center
Stay at this 3-star business-friendly hotel in Lowell. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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, Dec 24 - Wed, Dec 31
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$260 Roundtrip, found 2 days ago
$260
Roundtrip
found 2 days ago
Mon, Nov 24 - Wed, Dec 3
ATL
Hartsfield-Jackson Atlanta Intl.
MHT
Manchester-Boston Regional
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago
Mon, Nov 24 - Wed, Dec 3
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$268 Roundtrip, found 3 days ago
$268
Roundtrip
found 3 days ago
Thu, Nov 27 - Wed, Dec 3
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$311 Roundtrip, found 3 days ago
$311
Roundtrip
found 3 days ago