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
$654
per person
Sep 27 - Oct 1
found 18 hours ago
Roundtrip 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 Common and Salem Witch Museum are located nearby.
The stay was very comfortable. The front desk staff, Nancy was very helpful.
Reviewed on Aug 11, 2026
Encore Boston Harbor
$1,147
per person
Sep 27 - Oct 1
found 18 hours ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
The view was breathtaking as well as the food
Reviewed on Aug 12, 2026
Doubletree By Hilton Boston Logan Airport Chelsea
$800
per person
Sep 27 - Oct 1
found 18 hours ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
Stay at this hotel in Chelsea. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Budget friendly and convenient.
Reviewed on Aug 11, 2026
Arcadian Hotel
Coolidge Corner
$844
per person
Sep 27 - Oct 1
found 18 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Ac didn’t work
Reviewed on Aug 12, 2026
Battery Wharf Hotel, Boston Waterfront
North End
$1,874
per person
Sep 27 - Oct 1
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Maverick Suites at 40 Temple St
Beacon Hill
$881
per person
Sep 27 - Oct 1
found 18 hours ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
Stay at this aparthotel in Boston. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Boston Common and TD Garden are located nearby.
Top Hotel Deals
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 ...
Lamie's Inn and The Old Salt Restaurant
490 Lafayette Rd Hampton NH
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 ...
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 ...
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 ...
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. ...
Hampton Village Inn
660 Lafayette Road Hampton NH
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. ...
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 ...
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 ...
DoubleTree by Hilton Boston - Andover
123 Old River Rd Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Seabrook Inn
9 Stard Rd Seabrook NH
Book a stay at this business-friendly motel in Seabrook. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hampton Beach and Seabrook Beach ...
SpringHill Suites by Marriott Hampton Portsmouth
299 Exeter Road Hampton NH
Book a stay at this business-friendly hotel in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 ...
Hampton Falls Inn
11 Lafayette Rd Hampton Falls NH
Stay at this hotel in Hampton Falls. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Fairfield Inn & Suites by Marriott Portsmouth Exeter
138 Portsmouth Avenue Exeter NH
Book a stay at this business-friendly hotel in Exeter. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Red Roof Inn Salem
15 Red Roof Lane Salem NH
Stay at this hotel 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. ...
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, Oct 29
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$157
Roundtrip
found 2 hours ago
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$257
Roundtrip
found 2 hours ago
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$257
Roundtrip
found 2 hours ago
Tue, Oct 20 - Wed, Oct 28
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$257
Roundtrip
found 2 hours ago
Best points of interest in Chester
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