Hawley Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Hawley Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Omni Parker House
Downtown Boston
$1,016
per person
Oct 29 - Nov 3
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Faneuil Hall Marketplace and Boston Common are located nearby.
Boston Harbor Hotel
North End
$1,463
per person
Oct 29 - Nov 3
found 10 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Good Hotels Boston
South End
$1,351
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, laundry facilities, and bathrobes. Popular attractions Copley Square and Fenway Park are located nearby.
Very nice people and had excellent help!
Reviewed on Aug 7, 2026
Hotel AKA Boston Common
Downtown Boston
$1,080
per person
Oct 29 - Nov 3
found 10 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 Boston Common and Faneuil Hall Marketplace are located nearby.
Great staff, Saheed was pleasant and courteous. Lovely room, clean and nice modern furniture. The staff in the restaurant are very attentive and friendly, the bartender Kathleen made excellent mixed drinks and was pleasant to talk to.
Reviewed on Aug 14, 2026
Eurostars The Boxer
West End
$1,062
per person
Oct 29 - Nov 3
found 10 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.
Fairmont Copley Plaza, Boston
Back Bay
$1,253
per person
Oct 29 - Nov 3
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Top Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
The Yankee Inn
461 Pittsfield Rd Lenox MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
Stay at this motel in Lenox. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Williams Inn
101 Spring Street Williamstown MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Stay at this hotel in Hancock. Enjoy free parking, 2 hot tubs, and breakfast (surcharge). Our guests praise the property condition in our reviews. Popular attractions ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hotel On North
297 North Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
River Valley Inn
20 West St West Hatfield MA
Stay at this motel in West Hatfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Pioneer Valley Indoor Karting and Connecticut ...
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Willows Motel Williamstown
480 Main St Williamstown MA
Book a stay at this business-friendly motel in Williamstown. 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.
Thu, Sep 10 - Tue, Sep 15
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$245
Roundtrip
found 4 days ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$257
Roundtrip
found 20 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$269
Roundtrip
found 12 hours ago
Wed, Sep 23 - Thu, Oct 22
PDX
Portland Intl.
BOS
Logan Intl.
$279
Roundtrip
found 2 days ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 12 hours ago
Best points of interest in Charlemont
- Hawley Bog Preserve Vacations
- Parker Hill Vacations
- Jiminy Peak Mountain Resort Vacations
- Green Mountain National Forest Vacations
- Massachusetts Museum of Contemporary Art Vacations
- Williams College Vacations
- Berkshire East Ski Resort Vacations
- Mount Greylock Vacations
- Connecticut River Vacations
- The Clark Art Institute 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