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.
enVision Hotel Boston Everett
$708
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Washington (DCA) to Boston (BOS)
Book a stay at this business-friendly hotel in Everett. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
The room was very cute. There was some hair around the room but other than that not bad for a 1 night stay. The staff was lovely.
Reviewed on Aug 9, 2026
Boston Harbor Hotel
North End
$2,089
per person
Sep 30 - Oct 4
found 24 hours ago
Roundtrip non-stop flight included
Lancaster (LNS) 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.
Eurostars The Boxer
West End
$1,071
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Overall a great night
Reviewed on Aug 10, 2026
Fairmont Copley Plaza, Boston
Back Bay
$1,186
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Best location, centrally located!
Reviewed on Aug 10, 2026
The Godfrey Hotel Boston
Downtown Boston
$1,232
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Great location and service.
Everything is walking distance.
Reviewed on Aug 10, 2026
Omni Parker House
Downtown Boston
$1,234
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Faneuil Hall Marketplace and Boston Common are located nearby.
The Parker House has always been one of our faves. This time, however I chose a queen bed room because it was just my husband and I and we were not going to be in the room much.
Just because we had a queen bed, I did not think the bathroom was going to be TINY and ridiculously difficult to wash and use the toilet. This room was clearly meant for the hotel to just get an extra buck from an unsuspecting couple.
The price we paid was outrageous compared to the amenities in it. Not even a long mirror.
If you offer this to the market again, the price should be greatly reduced!!!
Reviewed on Aug 10, 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 ...
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 Veterans ...
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 ...
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. ...
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
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.
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$256
Roundtrip
found 2 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$269
Roundtrip
found 2 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 2 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 2 hours ago
Sat, Sep 12 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$287
Roundtrip
found 2 hours ago
Best points of interest in Chatham
- Chatham Lighthouse Beach Vacations
- Chatham Fish Pier Vacations
- Chatham Lighthouse Vacations
- Chatham Windmill Vacations
- Chatham Drama Guild Vacations
- Cockle Cove Beach Vacations
- Chatham Seaside Links Vacations
- Caleb Nickerson House Vacations
- Mayo House Vacations
- Monomoy National Wildlife Refuge Vacations
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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