Heath Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Heather Beaudry
Heath Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
South End
Price was $881, price is now $699 per person
$699
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3.5-star 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.
The Ritz-Carlton, Boston
Downtown Boston
Save 100% on your flight
Price was $2,048, price is now $1,381 per person
$1,381
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Porter Square Hotel
Porter Square
Price was $1,060, price is now $761 per person
$761
per person
Nov 23 - Nov 29
found 15 hours 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 $1,065, price is now $814 per person
$814
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.
The Bostonian Boston
Government Center
Price was $961, price is now $751 per person
$751
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.
Hotel Commonwealth
Fenway–Kenmore
Price was $1,079, price is now $849 per person
$849
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
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd, South Deerfield, MA
27.99 km from city center
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 ...
The Williams Inn
101 Spring Street, Williamstown, MA
31.57 km from city center
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
24 km from city center
Stay at this 3-star business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Mountaineer Inn
270 Handle Rd, West Dover, VT
32.52 km from city center
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Econo Lodge Brattleboro
515 Canal St, Brattleboro, VT
27.81 km from city center
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
The Covered Bridge Inn
1043 Putney Road, Brattleboro, VT
31.73 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Latchis Hotel
50 Main Street, Brattleboro, VT
29.25 km from city center
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. ...
Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
31.3 km from city center
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
Mount Snow Grand Summit Resort
89 Grand Summit Way, West Dover, VT
33.05 km from city center
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are ...
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road, Brattleboro, VT
32.07 km from city center
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. ...
The Porches Inn at Mass MoCA
231 River Street, North Adams, MA
24.27 km from city center
Stay at this 3.5-star business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The White House Inn
178 Route 9 East, Wilmington, VT
21.33 km from city center
Stay at this 3.5-star hotel in Wilmington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our ...
Hampton Inn & Suites Greenfield
184 Shelburne Rd, Greenfield, MA
18.94 km from city center
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. ...
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, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Wed, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$253 Roundtrip, found 6 days ago
$253
Roundtrip
found 6 days ago
Wed, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$258 Roundtrip, found 6 days ago
$258
Roundtrip
found 6 days ago
Wed, Sep 2 - Tue, Sep 8
PDX
Portland Intl.
BOS
Logan Intl.
$268 Roundtrip, found 6 days ago
$268
Roundtrip
found 6 days ago