Heath Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Heath 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 15 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 15 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.
The Godfrey Hotel Boston
Downtown Boston
$779
per person
Nov 23 - Nov 28
found 15 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 15 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 15 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.
Rooms are small but that’s expected in Boston. Great location near North Station and the Garden, and front desk staff was helpful and friendly.
Reviewed on Sep 12, 2026
The Revolution Hotel
South End
$721
per person
Nov 23 - Nov 28
found 15 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
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 ...
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
Colonial Motel
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Latchis Hotel
50 Main Street Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hideaway Inn Mt. Snow
270 Handle Rd West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are ...
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 ...
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 ...
Vikings Villages Resort
360 Viking Village Drive Guilford VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Porches Inn at Mass MoCA
231 River Street 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 breakfast and the helpful ...
Inn At Mount Snow
401 Vermont Rte 100 West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Snow Lake are located ...
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Hampton Inn & Suites Greenfield
184 Shelburne Rd Greenfield MA
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Valley Craft Ales
18 N Main St Wilmington VT
Stay at this lodge in Wilmington. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions South Main Street and Jim McGrath Gallery ...
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, Oct 28 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$319
Roundtrip
found 6 days ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$331
Roundtrip
found 4 days ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 4 days ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 4 days ago
Fri, Oct 23 - Wed, Nov 4
LAX
Los Angeles Intl.
BOS
Logan Intl.
$378
Roundtrip
found 5 days ago
Best points of interest in Charlemont
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