Brewster Vacations
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Brewster 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
Brewster Vacation Packages
Looking for ways save time and money on your upcoming holiday to Brewster? Then look no further, as the AARP Travel Center Powered by Expedia® is here to help. 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 Brewster the best one yet. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. We have an amazing selection of flights and lodgings, and local activities to choose from.
Brewster Hotels
You can choose from around 449 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Brewster hot spots, we have plenty of options available.
We have fantastic rates on everything from family-friendly resorts that satisfy all the vacation must-haves to inexpensive accommodations perfect for those on looking to save. You can search our vast catalog of possibilities and pick the hotel that is best for you. With AARP Travel Center's Brewster hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Brewster
Brewster is the ideal town when you need to a break from it all. With only around 9,918 people living here year-round, this cozy town is good for a quite vacation. Travelers come to enjoy Brewster's pleasant summers and the nearby coastline.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Book Together and Save
As an AARP Member, you get to cash in on all the great deals. You can save on select hotels worldwide, flights, and also rental cars. No matter what Brewster vacation bundle you pick, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Book today and get ready for your Brewster vacation.
Top Hotel Deals
The Villages at Ocean Edge
One Villages Drive Brewster MA
Book a stay at this beach resort in Brewster. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Charm on Main by Ocean Edge
2553 Main Street Brewster MA
Book a stay at this spa hotel in Brewster. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ocean Edge Golf Club and Rail Trail Bike Shop ...
The Mansion at Ocean Edge
2907 Main Street Brewster MA
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Brewster Green Resort
203 Lund Farm Way Brewster MA
Stay at this aparthotel in Brewster. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Ocean Edge Golf Club and Rail Trail Bike Shop are ...
Sea Meadow Inn
1187 Main St Brewster MA
Stay at this B&B in Brewster. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mayflower Beach and Cape Cod Museum of Natural History are ...
Candleberry Inn on Cape Cod
1882 Main St Brewster MA
Book a stay at this luxury B&B in Brewster. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Breakwater Beach and Rail Trail Bike Shop ...
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 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$284
Roundtrip
just found
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$323
Roundtrip
just found
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$343
Roundtrip
just found
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
just found
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
just found
Best neighborhoods in Brewster
Best points of interest in Brewster
- Ocean Edge Golf Club Vacations
- Breakwater Beach Vacations
- Nickerson State Park Vacations
- Cape Cod Museum of Natural History Vacations
- Paine's Creek Beach Vacations
- Rail Trail Bike Shop Vacations
- Captains Golf Course Vacations
- Crosby Landing Beach Vacations
- Brewster Historical Society Museum Vacations
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More Types of Hotels
- Hotels with Air Conditioning in Brewster
- Smoke Free Hotels in Brewster
- Hotels with WiFi in Brewster
- Hotel with wifi in Brewster
- Beach Hotels in Brewster
- Family Hotels in Brewster
- Hotels with a Pool in Brewster
- Hotels with Fireplaces in Brewster
- Hotel with a Concierge in Brewster
- Resorts & Hotels with Spas in Brewster
- Hotels with Hot Tubs in Brewster
- Hotels with Complimentary Breakfast in Brewster
- Hotels with Balconies in Brewster
- Hotels with Tennis Courts in Brewster
- Luxury Hotels in Brewster
- Hotels with Bars in Brewster
- Adults Only Resorts & Hotels in Brewster
- Lakefront Hotels in Brewster
- Hotels with an Indoor Pool in Brewster
- Cheap Hotels in Brewster
- Oceanfront Hotels in Brewster