Chatham Vacations

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Chatham Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Randolph - Boston

Comfort Inn Randolph - Boston

$750
per person
Oct 26 - Nov 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Randolph. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Blue Hills Reservation and South Shore Plaza are located nearby.
Staff was helpful. Room was clean and inexpensive.

Reviewed on Sep 23, 2026

Encore Boston Harbor

Encore Boston Harbor

Save 100% on your flight
$1,645
per person
Oct 26 - Nov 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
Save 100% on your flight
$1,790
per person
Oct 26 - Nov 1
found 11 hours ago
Roundtrip 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.
Holiday Inn Express & Suites Boston - Cambridge by IHG

Holiday Inn Express & Suites Boston - Cambridge by IHG

East Cambridge
Save 100% on your flight
$1,196
per person
Oct 26 - Nov 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

West End
Save 100% on your flight
$1,738
per person
Oct 26 - Nov 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
The Wyndham is in a great location for visiting Boston. The staff was very nice. Check in easy. The room was in need of a major remodel. Rug seemed dirty. There was a lot of mold in the shower. Bed was comfortable. I don’t think I would stay there again. 😔

Reviewed on Sep 24, 2026

The Inn on Arsenal

The Inn on Arsenal

$791
per person
Oct 26 - Nov 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Stay at this hotel in Watertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
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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

Chatham Bars Inn

297 Shore Rd Chatham MA
0.87 km from city center
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

Chatham Wayside Inn

512 Main St Chatham MA
0.43 km from city center
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

Greyfinch Chatham Inn

946 Main Street (Rte 28) Chatham MA
0.86 km from city center
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. ...
Queen Anne Inn

Queen Anne Inn

70 Queen Anne Rd Chatham MA
0.41 km from city center
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

Pleasant Bay Village Resort

1191 Orleans Road Chatham MA
3.82 km from city center
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 ...
Chatham Seafarer Inn

Chatham Seafarer Inn

2079 Main St Chatham MA
3.9 km from city center
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

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA
28.99 km from city center
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

Bayside Resort Hotel

225 Route 28 West Yarmouth MA
24.65 km from city center
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

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA
25.09 km from city center
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. ...
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA
29.46 km from city center
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 ...
Lighthouse Inn

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA
17.59 km from city center
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 Villages at Ocean Edge

The Villages at Ocean Edge

One Villages Drive Brewster MA
12.29 km from city center
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

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA
14.49 km from city center
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 ...
Hyannis Harbor Hotel

Hyannis Harbor Hotel

213 Ocean St Hyannis MA
26.73 km from city center
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 ...
Hyannis Travel Inn

Hyannis Travel Inn

18 North St Hyannis MA
26.96 km from city center
Stay at this hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
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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.

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