Ashland Vacations
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Ashland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
Coolidge Corner
$634
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
I tried for weeks to change the date of my reservation due to the event I was going to was postponed. There was availability for the new date and the prices were cheaper. I offered to keep the more expensive rate, but please let me change the date. I still wanted to give the hotel my business. After zillions of calls and emails between myself and the hotel and Expedia and the hotel, it was not until THE DAY of the original check-in that the hotel responded and basically said nope, and no refund. Weeks of stress for nothing!
Reviewed on Sep 13, 2026
Boston Harbor Hotel
North End
$1,170
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 Faneuil Hall Marketplace are located nearby.
What a great hotel
Reviewed on Sep 13, 2026
Battery Wharf Hotel, Boston Waterfront
North End
$845
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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.
Great location, beautiful facility…. Great amenities… very friendly and helpful staff!
Reviewed on Sep 13, 2026
The Ritz-Carlton, Boston
Downtown Boston
$1,173
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Book a stay at this 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.
Incredible stay and beautiful room.
Reviewed on Sep 10, 2026
The Langham, Boston
Downtown Boston
$1,250
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. 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.
Beautiful hotel in a great location. The staff were lovely. My stepson loved the paddington bear bowl of cookies and sprinkles. Nice touch.
Reviewed on Sep 13, 2026
Bricco Suites
North End
$784
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Popular attractions Faneuil Hall Marketplace and Boston Harbor are located nearby.
Bricco Suites was a wonderful place to stay! The location is centrally located and about 2 blocks from the subway making it very easy to explore. We loved the nearby authentic Italian food and found that Quattro had the best pizza - similar to pizza we have had in Florence and Rome!! YUM!
The bed was comfortable and we slept well the five days we were there. AC worked great and was appreciated after long, hot days of exploring! The room was clean and well appointed with 2 night stands, a fridge, dresser, bench, chair, sink, coffee pot, utensils, ice bucket, and a desk. We had room 304 which was up one flight of stairs. The stairs are narrow and winding, so keep that in mind if you have physical limitations.
We enjoyed our stay and would absolutely stay there again!
I have two recommendations:
1) A small shelf in the bathroom by the sink since the counter space was limited. Definitely not a deal breaker though as I had a hanging toiletry bag.
2) A TV with the ability to stream. Winding down at night it would be nice to have streaming as an option, we made do and enjoyed some SVU and Friends reruns.
Reviewed on Sep 13, 2026
Ashland Vacation Packages
Looking to save time and money on your next vacation to Ashland? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Ashland incredible. In only a few clicks, you can pick the best Ashland vacation package for you. We have a fabulous choice of flights and hotels, and local endeavors to select from.
Hotels in Ashland
You can choose from around 2126 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Ashland hot spots, we have plenty of options available.
We have competitive rates on everything from luxury hotels that satisfy all the vacation must-haves to affordable accommodations perfect for those on a budget. You can scan all the possibilities and pick the hotel that is best for you. With AARP Travel Center's Ashland hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Ashland
Ashland has around 17,573 people that call this city their home. If you needed a break from the bustle of a big city, then you chose the perfect place. With Ashland's growing artistic community and plenty of interest for history buffs you may have a hard time fitting everything into one trip.
You can also check out our "Things to Do" tab for more inspiration or to reserve an activity in Ashland.
Package Your Ashland Vacation and Save
With so much happening in Ashland, you'll be wanting to plan your outings, not spending time to searching for the hotel with the lowest rate. The AARP Travel Center Powered by Expedia® allows you to easily book everything you need, and save a little money. You can plan your entire holiday, including things to do in Ashland from just one place. The hardest packing you'll have to do is for your suitcase. Book today and save!
Top Hotel Deals
The Midtown Hotel MOD Collection by Sonesta
220 Huntington Avenue Boston MA
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.
citizenM Boston Back Bay
408 Newbury street Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square are located ...
Arcadian Hotel
1200 Beacon St Brookline MA
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 ...
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant ...
Copley Square Hotel, a FOUND Hotel
47 Huntington Ave Boston MA
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the ...
Hotel Commonwealth
500 Commonwealth Ave Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Copley House
239 W Newton St Boston MA
Stay at this guesthouse in Boston. Enjoy free WiFi, parking (surcharge), and laundry facilities. Our guests praise the helpful staff and the clean rooms in our ...
Hampton Inn & Suites Boston Crosstown Center
811 Massachusetts Ave Boston MA
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
DoubleTree Suites by Hilton Hotel Boston - Cambridge
400 Soldiers Field Road Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
Boston Marriott Copley Place
110 Huntington Ave Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Sheraton Boston, a Marriott Hotel
39 Dalton St Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise ...
Bedford Plaza Hotel - Boston
340 Great Road Bedford MA
Stay at this hotel in Bedford. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Burlington Mall and Minute Man National Historical ...
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. ...
The Atlas Hotel
40 Western Avenue Boston MA
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway ...
The Colonnade Hotel Back Bay
120 Huntington Avenue Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our ...
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.
Tue, Nov 10 - Tue, Nov 17
LAX
Los Angeles Intl.
BOS
Logan Intl.
$337
Roundtrip
found 16 hours ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$352
Roundtrip
found 16 hours ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 16 hours ago
Tue, Nov 10 - Fri, Nov 13
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 16 hours ago
Fri, Nov 13 - Sat, Nov 14
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 16 hours ago
Best points of interest in Ashland
- Ashland State Park Vacations
- Fenway Park Vacations
- Harvard University Vacations
- Gillette Stadium Vacations
- Harvard Square Vacations
- Massachusetts Institute of Technology Vacations
- Boston University Vacations
- Northeastern University Vacations
- Boston College Vacations
- Hynes Convention Center Vacations
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