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 Westin Boston Seaport District
Seaport District
$674
per person
Nov 23 - Nov 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Battery Wharf Hotel, Boston Waterfront
North End
$771
per person
Nov 23 - Nov 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) 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 clean rooms in our reviews. Popular attractions Boston Harbor and Faneuil Hall Marketplace are located nearby.
Friendly and welcoming staff, spacious clean room, great location. Would definitely stay here again.
Reviewed on Sep 13, 2026
The Godfrey Hotel Boston
Downtown Boston
$779
per person
Nov 23 - Nov 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Arcadian Hotel
Coolidge Corner
$739
per person
Nov 23 - Nov 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Eurostars The Boxer
West End
$812
per person
Nov 23 - Nov 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Enjoyed the stay!! Plus the ghost in my room!!
Reviewed on Sep 13, 2026
The Revolution Hotel
South End
$721
per person
Nov 23 - Nov 28
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 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.
Top Hotel Deals
Hilton Garden Inn Tewksbury Andover
4 Highwood Drive Tewksbury MA
Book a stay at this business-friendly hotel in Tewksbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Express Chelmsford by IHG
8 Independence Drive Chelmsford MA
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 ...
Comfort Inn Manchester Airport
298 Queen City Ave Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd Andover MA
Book a stay at this 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
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Park View Inn - Salem
109 S Broadway Salem NH
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. ...
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr Salem NH
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Methuen Inn and Conference Center
159 Pelham Street Methuen MA
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 ...
Sonesta ES Suites Andover Boston
4 Tech Drive Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
DoubleTree by Hilton Manchester Downtown
700 Elm St. Manchester NH
Stay at this hotel in Manchester. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
SpringHill Suites by Marriott Boston/Andover
550 Minuteman Rd Andover MA
Stay at this hotel in Andover. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
DoubleTree by Hilton Boston - Andover
123 Old River Rd Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Motel 6 Nashua, NH - South
77 Spit Brook Rd Nashua NH
Stay at this motel in Nashua. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Econo Lodge Manchester
75 W Hancock Street Manchester NH
Stay at this hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Northeast Delta Dental Stadium and Southern New Hampshire ...
SpringHill Suites by Marriott Manchester-Boston Regional Airport
975 Perimeter Rd Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and ...
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.
Sun, Oct 18 - Thu, Nov 5
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$222
Roundtrip
found 3 days ago
Sat, Oct 24 - Sat, Oct 31
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$279
Roundtrip
found 6 days ago
Sun, Oct 18 - Thu, Nov 5
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$363
Roundtrip
found 3 days ago
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$382
Roundtrip
found 1 day ago
Best points of interest in Litchfield
- Tee Off at Mel's Vacations
- Southern New Hampshire University Arena Vacations
- Canobie Lake Park Vacations
- University of Massachusetts Lowell Vacations
- Merrimack Premium Outlets Vacations
- Tuscan Village Salem Vacations
- Merrimack College Vacations
- Southern New Hampshire University Vacations
- Saint Anselm College Vacations
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