Windham Vacations
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Windham Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
Coolidge Corner
$736
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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.
We were visiting our child, and it was a perfect place to stay
Reviewed on Aug 7, 2026
Fairmont Copley Plaza, Boston
Back Bay
$1,337
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The common areas are beautifully historic as are the rooms. The rooms could definitely use new furniture and carpet. The beds and pillows are fabulous. The TV is adequate. In the closet is an iron and board, as well as a steamer. A safe, slippers and robe are provided as well as shoeshine and shoehorn. A Nespresso is provided with regular coffee and decaf pods. There is a kettle and about 4 choices of teas. A coffee service is provided. As far as the bar, full and small bottles of wine, small bottles of alcohol, mixers, soda and still/sparkling water are provided as well as glassware and wine opener. I don't know where there is ice other than at the restaurant. There is no microwave. The snacks range from trail mix, M&M's, cookies, etc. The room service menu for lunch/dinner does not have a good selection for vegetarians. The restaurant on the main floor looks very warm and cozy. It was quiet even though there were a lot of families present. It is within walking distance of many boutiques and restaurants. Also, within walking distance of Fenway Park. Lovely staff and the doorman we encountered was particularly kind and helpful.
Reviewed on Aug 6, 2026
The Godfrey Hotel Boston
Downtown Boston
$1,184
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Excellent stay. The only thing that was an issue was the beds are extremely soft. If you have back issues or as in our case recovering from a shoulder surgery the beds was definitely too soft. The hotel is known for cloud soft beds so we should have researched that a bit. The hotel however was wonderful and a great location.
Reviewed on Aug 7, 2026
Eurostars The Boxer
West End
$1,320
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Great location. Good staff. Nice size rooms with amenities.
Reviewed on Aug 7, 2026
The Revolution Hotel
South End
$819
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Concord Hotel
South End
$952
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Very good location! And clean building and the room.
Check in process definitely needs to have more details - specifically your room#, as its a 4story building
Communication was on top, they are really looking forward to solve your request.
Reviewed on Aug 4, 2026
Windham Vacation Packages
Hoping to save money and time on your next vacation to Windham? Then look no further, as the AARP Travel Center Powered by Expedia® is here to help. We're here to book everything you'll need to make your Windham trip one to remember. With only a few clicks, you can select the best vacation package for you. AARP Travel Center has a fabulous selection of accommodations and flight, as well as Windham activities to select from.
Windham Hotel Deals
With 427 hotels and resorts in Windham to choose from, you are bound to find one that meets your needs.
We have fantastic rates on everything from family-friendly resorts that check off all the vacation must-haves to inexpensive hotels perfect for those on looking to save. You can browse all the possibilities and pick the accommodation that is ideal for you. With AARP Travel Center's Windham hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Windham
Windham has about 14,439 people that call this city their home. If you needed a break from the bustle of a big city, then you picked the right town. With this area's burgeoning artistry scene and a rich past that is a beacon for history buffs you may have a hard time fitting everything into one trip.
If you are looking for more, then head over to our "Things to Do" page for more inspiration or to book an activity in Windham.
Package Your Windham Vacation and Save
As an AARP Member, you get to benefit from all the great savings. You can save on select hotels worldwide, flights, and also rental cars. No matter what Windham vacation bundle you select, your membership savings helps you get a great deal. So what are you waiting for? Bundle today and get ready for your Windham vacation.
Top Hotel Deals
Hilton Garden Inn Tewksbury Andover
4 Highwood Drive Tewksbury MA
Book a stay at this business-friendly hotel in Tewksbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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 ...
Courtyard by Marriott Boston Billerica/Bedford
270 Concord Rd Billerica MA
Book a stay at this business-friendly hotel in Billerica. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
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 ...
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. ...
Holiday Inn Express Chelmsford by IHG
8 Independence Drive Chelmsford MA
Book a stay at this business-friendly hotel in Chelmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 ...
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 ...
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 ...
Homewood Suites by Hilton Boston/Billerica
35 Middlesex Turnpike Billerica MA
Book a stay at this business-friendly hotel in Billerica. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Express & Suites Merrimack – Nashua by IHG
4 Amherst Rd Merrimack NH
Book a stay at this business-friendly hotel in Merrimack. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sonesta ES Suites Andover Boston
4 Tech Drive Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
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.
Fri, Sep 25 - Fri, Oct 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$259
Roundtrip
found 3 days ago
Fri, Sep 25 - Fri, Oct 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$277
Roundtrip
found 3 days ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 4 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 4 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 4 hours ago
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