Chatham Vacations

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Chatham Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Westin Waltham-Boston

The Westin Waltham-Boston

Save 100% on your flight
$1,081
per person
Sep 16 - Sep 23
found 7 hours ago
Roundtrip flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this business-friendly hotel in Waltham. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction Walden Pond is located nearby.
Eurostars The Boxer

Eurostars The Boxer

West End
Save 100% on your flight
$2,227
per person
Sep 16 - Sep 23
found 7 hours ago
Roundtrip flight included
Milwaukee (MKE) 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.
The Atlas Hotel

The Atlas Hotel

Allston
Save 100% on your flight
$1,873
per person
Sep 16 - Sep 23
found 7 hours ago
Roundtrip flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
Excellent hotel

Reviewed on Aug 14, 2026

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

North Brookline
Save 100% on your flight
$1,578
per person
Sep 16 - Sep 23
found 7 hours ago
Roundtrip flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this apartment in Brookline. Enjoy free WiFi, parking (surcharge), and air conditioning. Popular attractions Fenway Park and Harvard Square are located nearby.
This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells. Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not recommended. It is not the sunny, pristine, and secure apartment that appears in the photos.

Reviewed on Jul 6, 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
Save 100% on your flight
$4,107
per person
Sep 16 - Sep 23
found 7 hours ago
Roundtrip flight included
Milwaukee (MKE) 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.
Arcadian Hotel

Arcadian Hotel

Coolidge Corner
Save 100% on your flight
$1,491
per person
Sep 16 - Sep 23
found 7 hours ago
Roundtrip flight included
Milwaukee (MKE) 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.
The room was dirty (bathroom) and the beds were a mess like a child made it. The receptionist was helpful so she gave us another room, which also was a mess, so she gave me another room, which finally was decent, but overall I did not like the hotel.

Reviewed on Aug 14, 2026

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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 ...
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 Veterans ...
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. ...
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 ...
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 ...
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. ...
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. ...
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 ...
Cape Sands Inn

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA
24.99 km from city center
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

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 ...
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. ...
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

553 Main Street West Yarmouth MA
22.82 km from city center
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 ...
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

573 Main Street (Route 28) West Yarmouth MA
22.76 km from city center
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

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 ...
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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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