Chatham Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chatham 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
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 ...
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 ...
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 ...
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. ...
Chatham Seafarer Inn
2079 Main St Chatham MA
Stay at this hotel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cockle Cove Beach and Ridgevale Beach are located ...
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. ...
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. ...
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. ...
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 ...
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 Mariner Resort Cape Cod by The Red Collection
573 Main Street (Route 28) West Yarmouth MA
Book a stay at this family-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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. ...
Holiday Hill Inn & Suites
352 Main Street Dennis Port MA
Book a stay at this family-friendly motel in Dennis Port. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
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
found 4 hours ago
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$323
Roundtrip
found 4 hours ago
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$343
Roundtrip
found 4 hours ago
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 4 hours ago
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 4 hours ago
Best points of interest in Chatham
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
All accommodation types in Chatham
More Types of Hotels
- Hotels with Air Conditioning in Chatham
- Beach Hotels in Chatham
- Hotels with WiFi in Chatham
- Hotel with wifi in Chatham
- 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