Chester Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College
Price was $530, price is now $367 per person
$367
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Rice's Beach are located nearby.
Boston Harbor Hotel
North End
Save 100% on your flight
Price was $2,312, price is now $1,352 per person
$1,352
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 Boston Harbor are located nearby.
The Godfrey Hotel Boston
Downtown Boston
Save 100% on your flight
Price was $917, price is now $664 per person
$664
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 New England Aquarium are located nearby.
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
Save 100% on your flight
Price was $952, price is now $697 per person
$697
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this business-friendly 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.
Raffles Boston
Back Bay
Save 100% on your flight
Price was $2,474, price is now $1,820 per person
$1,820
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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.
Studio Allston Hotel
Brighton
Save 100% on your flight
Price was $751, price is now $554 per person
$554
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. 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 Harvard Square and Fenway Park are located nearby.
Top Hotel Deals
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr Salem NH
20.36 km from city center
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 ...
Comfort Inn Manchester Airport
298 Queen City Ave Manchester NH
17.78 km from city center
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 ...
Park View Inn - Salem
109 S Broadway Salem NH
20.85 km from city center
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 Boston-Andover
131 River Rd Andover MA
29.89 km from city center
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 ...
Motel 6 Nashua, NH - South
77 Spit Brook Rd Nashua NH
31.7 km from city center
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 ...
Best Western Plus Executive Court Inn & Conference Center
13500 S Willow St Manchester NH
13.01 km from city center
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 ...
Lamie's Inn and The Old Salt Restaurant
490 Lafayette Rd Hampton NH
34.22 km from city center
Book a stay at this business-friendly inn in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the restaurant and the helpful staff ...
DoubleTree by Hilton Manchester Downtown
700 Elm St. Manchester NH
17.18 km from city center
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 ...
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
28.21 km from city center
Stay at this cabin in Epsom. Enjoy free parking, patios, and climate control. Popular attractions James Park and Epsom Public Library are located nearby.
Methuen Inn and Conference Center
159 Pelham Street Methuen MA
25.6 km from city center
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 ...
Hampton Village Inn
660 Lafayette Road Hampton NH
34.53 km from city center
Stay at this hotel in Hampton. 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
30.13 km from city center
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Comfort Inn Concord South End
71 Hall St Concord NH
33.77 km from city center
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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.
Sat, Sep 5 - Sun, Sep 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$201 Roundtrip, found 1 hour ago
$201
Roundtrip
found 1 hour ago
Tue, Aug 11 - Tue, Sep 1
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$280 Roundtrip, found 1 hour ago
$280
Roundtrip
found 1 hour ago