Brewster Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Brewster Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Iris Hotel Boston
Coolidge Corner
$1,261
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
The stay at the Iris Hotel Boston was perfect! The staff went above and beyond to accommodate, make comfortable, welcome us. The bartender was outstanding!
The room was beautiful with every need anticipated. Convenient and fun neighborhood with many restaurant, cuisine, shopping and transportation options.
I will certainly be back!
Reviewed on Aug 11, 2026
Furnished Apartment Near Longwood
North Brookline
$1,742
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Stay at this apartment in Brookline. Enjoy free WiFi, parking (surcharge), and air conditioning. Popular attractions Fenway Park and Harvard Square are located nearby.
This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells.
Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not recommended. It is not the sunny, pristine, and secure apartment that appears in the photos.
Reviewed on Jul 6, 2026
The Concord Hotel
South End
$1,445
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Stay at this aparthotel in Boston. Enjoy free WiFi and air conditioning. Popular attractions Copley Square and Fenway Park are located nearby.
The building is not new. Hallway was musty. Boxes in the entry way. People sitting on the front stoop smoking, Dirty wash cloth on the stair railing.
Management company only communicated via text and wasn't very friendly at all.
I would not stay there again.
Reviewed on Aug 9, 2026
The Atlas Hotel
Allston
$1,641
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
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 Park are located nearby.
The hotel was clean and well maintained. Very innovative designed. The staff was constantly hospitable - opening every door when we enter. The only downside was the room next to us was very loud on our last night which kept us up most of the night - nothing to do with the hotel. I didn’t complain and am hoping for some compensation back.
Reviewed on Aug 10, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
$2,157
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Burlington Mall and Minute Man National Historical Park are located nearby.
This Inn is a beautiful old building with a long history. It is located within easy walking distance of downtown Lexington with all its history. The Inn had wonderful rooms, a great staff and a top rate restaurant all in one place. Highly recommend!
Reviewed on Jul 13, 2026
The Charles Hotel
West Cambridge
$2,610
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
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 452 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. ...
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. ...
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 ...
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 ...
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 Ocean Edge Golf Club and Brewster Ladies' ...
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 Ocean Edge Golf Club and Mayflower Beach are located ...
The Old Manse Inn
1861 Main St. Brewster MA
Book a stay at this luxury B&B in Brewster. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ocean Edge Golf Club and Brewster Ladies' ...
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, Sep 1 - Tue, Sep 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$204
Roundtrip
found 2 hours ago
Tue, Sep 1 - Tue, Sep 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$269
Roundtrip
found 2 hours ago
Mon, Sep 21 - Tue, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 2 hours ago
Wed, Sep 23 - Wed, Sep 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
just found
Wed, Sep 23 - Wed, Sep 30
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
just found
Best neighborhoods in Brewster
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
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