Chatham Vacations

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Chatham Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Inn on Arsenal

The Inn on Arsenal

$786
per person
Nov 2 - Nov 8
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
Bricco Suites

Bricco Suites

North End
$1,563
per person
Nov 9 - Nov 16
found 6 hours ago
Roundtrip flight included
Milwaukee (MKE) 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.
Would not stay here again. There is no elevator, we were on the 3rd floor dragging bags upstairs. Noisy late from the restaurant downstairs, and early from trash/deliveries/etc. Location is great, in the heart of Little Italy. Overpriced.

Reviewed on Sep 24, 2026

SpringHill Suites by Marriott Boston Peabody

SpringHill Suites by Marriott Boston Peabody

$904
per person
Nov 2 - Nov 8
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this business-friendly hotel in Peabody. 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 Salem Witch Museum and Salem Common are located nearby.
The Revolution Hotel

The Revolution Hotel

South End
$1,298
per person
Nov 9 - Nov 16
found 6 hours ago
Roundtrip flight included
Milwaukee (MKE) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Front desk was helpful and the hotel was in a great location, nice neighborhood for walking and subway. Coffee bar was out of order several mornings which set tourists in search of morning coffee.

Reviewed on Sep 25, 2026

Arcadian Hotel

Arcadian Hotel

Coolidge Corner
$1,260
per person
Nov 9 - Nov 16
found 6 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.
Studio Allston Hotel

Studio Allston Hotel

Brighton
$1,201
per person
Nov 9 - Nov 16
found 6 hours ago
Roundtrip flight included
Milwaukee (MKE) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. 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 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 ...
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 ...
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 ...
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. ...
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. ...
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 ...
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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