Medway Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Medway 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 22 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 22 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.
I highly recommend Encore. I didn’t have a chance to experience the spa but the staff in general, was very helpful and friendly. I have yet to have a bad meal there. The food is extraordinary. I will definitely return to Encore soon.
Reviewed on Aug 12, 2026
Doubletree By Hilton Boston Logan Airport Chelsea
$800
per person
Sep 27 - Oct 1
found 22 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.
Room was super clean and the staff was very very helpful. I enjoyed the stay. It was 3 of us in a room and they also gave us a roller bed so each of got our own bed. Excellent stay
Reviewed on Aug 12, 2026
Arcadian Hotel
Coolidge Corner
$844
per person
Sep 27 - Oct 1
found 22 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.
Battery Wharf Hotel, Boston Waterfront
North End
$1,874
per person
Sep 27 - Oct 1
found 15 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.
Very nice hotel. Initial room we were given had drain smell but we were moved quickly. Staff were generally very helpful too.
Reviewed on Aug 12, 2026
Maverick Suites at 40 Temple St
Beacon Hill
$881
per person
Sep 27 - Oct 1
found 22 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
Four Points by Sheraton Boston Newton
320 Washington Street Newton MA
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
Garner Hotel Brockton - Boston by IHG
405 Westgate Dr. Brockton MA
Book a stay at this business-friendly hotel in Brockton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Sonesta Select Boston Foxborough Mansfield
35 Foxborough Boulevard Foxborough MA
Book a stay at this business-friendly hotel in Foxborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Sheraton Boston Needham Hotel
100 Cabot St Needham MA
Book a stay at this business-friendly hotel in Needham. Enjoy breakfast (surcharge), a fitness center, and parking (surcharge). Our guests praise the helpful ...
Hampton Inn & Suites Boston/Waltham
135 2nd Ave Waltham MA
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Westin Waltham-Boston
70 Third Avenue Waltham MA
Book a stay at this business-friendly hotel in Waltham. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and ...
Hampton Inn Boston/Braintree
215 Wood Rd Braintree MA
Book a stay at this business-friendly hotel in Braintree. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Boston Hotel
40 Mt Hood Road Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
The Inn on Arsenal
100 N Beacon St Watertown MA
Stay at this hotel in Watertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Embassy Suites by Hilton Boston Waltham
550 Winter Street Waltham MA
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, 2 restaurants, and a 24-hour fitness center. Our guests praise the breakfast and ...
Hampton Inn & Suites Watertown Boston
25 Bond Street Watertown MA
Book a stay at this business-friendly hotel in Watertown. Enjoy free breakfast, a fitness center, and parking (surcharge). Our guests praise the breakfast and ...
Boston Marriott Newton
2345 Commonwealth Avenue Newton MA
Book a stay at this business-friendly hotel in Newton. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and ...
Holiday Inn Express & Suites Norwood-Boston Area by IHG
225 Norwood Park S Norwood MA
Book a stay at this business-friendly hotel in Norwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Plus Waltham Boston
380 Winter Street Waltham MA
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Sonesta Select Boston Milford
10 Fortune Blvd Milford MA
Book a stay at this business-friendly hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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.
Mon, Oct 26 - Tue, Oct 27
LAX
Los Angeles Intl.
BOS
Logan Intl.
$204
Roundtrip
found 1 hour ago
Fri, Sep 25 - Tue, Oct 20
LAX
Los Angeles Intl.
BOS
Logan Intl.
$218
Roundtrip
found 18 hours ago
Tue, Nov 3 - Tue, Nov 10
LAX
Los Angeles Intl.
BOS
Logan Intl.
$269
Roundtrip
found 19 hours ago
Mon, Sep 21 - Sat, Sep 26
LAX
Los Angeles Intl.
PVD
T.F. Green
$277
Roundtrip
found 21 hours ago
Mon, Sep 21 - Tue, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 5 hours ago
Best points of interest in Medway
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