Chatham Vacations
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Chatham Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
Coolidge Corner
$972
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
This place is like putting lipstick on a pig. I think it may have been an old motel or something so they renovated it to look nice but everything is old.
Reviewed on Sep 5, 2026
Boston Harbor Hotel
North End
$2,217
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Fairmont Copley Plaza, Boston
Back Bay
$2,027
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
We love staying here - so historic and the oak bar is lovely. I think the rooms could use an upgrade - stains on the carpet, cracked sink, etc..
Reviewed on Sep 4, 2026
Eurostars The Boxer
West End
$1,639
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Staypineapple, A Delightful Hotel, South End
South End
$1,249
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free bicycles on site, a 24-hour front desk, and a fireplace in the lobby. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Pros:
1. The price was fair considering it was move-in week for my daughter’s college.
2. The location was great - an easy walk to Emerson College and the T-stop so accessible to everything.
3. The staff was very friendly.
4. They gave me two free beverages upon check-in.
Cons:
1. The water pressure in the shower was awful.
2. My room was next to the door to the hallway, and every time someone would go thru the door, it would slam shut and wake me up. While I appreciated that they put a door to lessen the noise from the elevator, I wish they had put a soft-close mechanism on the door to keep it from slamming.
3. The housekeeping card in the room said that they would refresh the bedsheets every other day. I requested housecleaning on my second day, and while they replaced the towels, they didn’t replace the sheets (I could tell because there were the same stains from the night before), and they didn’t even vacuum. There was still hair in the shower.
4. The bathroom sink was so small that whenever I washed my face, water would get everywhere. It was mounted too low on the wall.
5. There was water damage on the bedside table and on the floorboards. The room could have used some better maintenance.
Reviewed on Sep 5, 2026
Iris Hotel Boston
Coolidge Corner
$1,189
per person
Oct 11 - Oct 15
found 9 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Great stay
Reviewed on Sep 5, 2026
Chatham Vacation Packages
Trying to figure out a way to bundle your Chatham flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. 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 Chatham the best one yet. In just a few clicks, you can select the best Chatham vacation package for you and your family. AARP Travel Center has a fabulous choice of flights and lodgings, and Chatham endeavors to pull from.
Chatham Hotels
Our listings include hotels that are close to all the Chatham points of interest, and some that are just outside the city center for a more restful retreat.
We have great deals on everything from all-inclusive resorts that meet all the vacation must-haves to affordable accommodations perfect for those on wanting to save a little money. You can scan all the possibilities and choose the accommodation that is best for you and your family. With AARP Travel Center's Chatham hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Chatham
Chatham is the ideal place when you have to get away from it all. With only around 6,143 people living here year-round, this hidden-gem is just right for a quite vacation. Guests come to take advantage of Chatham's pleasant summers and the nearby coastline.
If you are looking for more, then head over to our "Things to Do" tab for more inspiration or to reserve an activity in Chatham.
Package Your Chatham Vacation and Save
With so much happening in Chatham, you'll be wanting to focus on your outings, not spending time to searching for the cheapest hotel. AARP Travel Center allows you to quickly get all you want, and save money while doing it. You can coordinate your whole vacation, including activities in Chatham from only one place. The hardest packing you'll have to do is for your suitcase. Bundle today and save!
Top Hotel Deals
Chatham Bars Inn
297 Shore Rd Chatham MA
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
Chatham Wayside Inn
512 Main St Chatham MA
Book a stay at this golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Pleasant Bay Village Resort
1191 Orleans Road Chatham MA
Stay at this hotel in Chatham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Queen Anne Inn
70 Queen Anne Rd Chatham MA
Stay at this hotel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Chatham ...
Greyfinch Chatham Inn
946 Main Street (Rte 28) Chatham MA
Book a stay at this family-friendly motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
The Hawthorne
196 Shore Rd Chatham MA
Book a stay at this beach hotel in Chatham. Enjoy free WiFi, free parking, and a private beach. Popular attractions Chatham Seaside Links and Mayo House are ...
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions ...
Bayside Resort Hotel
225 Route 28 West Yarmouth MA
Book a stay at this beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Holiday Inn Express Hyannis Cape Cod by IHG
1470 Iyannough Road Hyannis MA
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Uncommoner Hotel by Reverie Boutique Collection
135 Route 28 West Yarmouth MA
Book a stay at this beach hotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. ...
Cape Sands Inn
149 Main St - RT 28 West Yarmouth MA
Book a stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the pool and the helpful staff ...
Lighthouse Inn
1 Lighthouse Inn Rd West Dennis MA
Book a stay at this beach hotel in West Dennis. Enjoy free WiFi, free parking, and private plunge pools. Our guests praise the helpful staff in our reviews. ...
Hyannis Harbor Hotel
213 Ocean St Hyannis MA
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our ...
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. ...
Freebird Motor Lodge by Reverie Boutique Collection
553 Main Street West Yarmouth MA
Book a stay at this business-friendly motel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful ...
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, Sep 21 - Fri, Oct 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$264
Roundtrip
found 4 days ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$327
Roundtrip
found 3 days ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$337
Roundtrip
found 3 days ago
Thu, Oct 1 - Wed, Oct 7
LAX
Los Angeles Intl.
BOS
Logan Intl.
$337
Roundtrip
found 6 days ago
Tue, Oct 20 - Sat, Oct 24
LAX
Los Angeles Intl.
BOS
Logan Intl.
$339
Roundtrip
found 4 days ago
Best points of interest in Chatham
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All accommodation types in Chatham
More Types of Hotels
- Hotels with Air Conditioning in Chatham
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- Smoke Free Hotels in Chatham
- Family Hotels in Chatham
- Hotels with a Pool in Chatham
- Hotels with Fireplaces in Chatham
- Hotel with a Concierge in Chatham
- Hotels with Bars in Chatham
- Hotels with Complimentary Breakfast in Chatham
- Hotels with Balconies in Chatham
- Luxury Hotels in Chatham
- Hotels with smoking rooms in Chatham
- Hotels with Hot Tubs in Chatham
- Hotels with Tennis Courts in Chatham
- Cheap Hotels in Chatham
- Resorts & Hotels with Spas in Chatham
- Oceanfront Hotels in Chatham
- Pet-friendly Hotels in Chatham
- Adults Only Resorts & Hotels in Chatham
- Hotels with Early Check-in in Chatham