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.
Battery Wharf Hotel, Boston Waterfront
North End
$837
per person
Nov 24 - Nov 29
found 7 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.
Boston Harbor Hotel
North End
$1,375
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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.
Everything about this hotel is wonderful! We would definitely stay here again.
Reviewed on Sep 8, 2026
Raffles Boston
Back Bay
$1,281
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Mandarin Oriental, Boston
Back Bay
$1,517
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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 room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Great hotel in great location.
Staff earned five star status.
Reviewed on Sep 6, 2026
The Langham, Boston
Downtown Boston
$1,208
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
We loved it.
Reviewed on Sep 7, 2026
The Colonnade Hotel Back Bay
Back Bay
$1,459
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Nice roof-top pool; excellent location.
Reviewed on Sep 9, 2026
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 ...
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 ...
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 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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Holiday Inn Express & Suites Merrimack – Nashua by IHG
4 Amherst Rd Merrimack NH
Book a stay at this business-friendly hotel in Merrimack. Enjoy free breakfast, free WiFi, and free parking. 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.
Sun, Oct 18 - Thu, Nov 5
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$222
Roundtrip
found 7 hours ago
Sat, Oct 24 - Sat, Oct 31
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$279
Roundtrip
found 2 days ago
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$309
Roundtrip
found 1 day ago
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$324
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
- Merrimack College Vacations
- Southern New Hampshire University Vacations
- Tuscan Village Salem 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