Chatham Vacations

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Find the Best Chatham Vacation Packages

Chatham Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is AED 1,389 per night from Dec 29 to Dec 30
AED 1,389
AED 1,669 total
29 Dec - 30 Dec
includes taxes & fees
9.2/10 Wonderful! (798 reviews)
An incredible stay. Room at the main inn could use some updating. Just a bit tired with cracked tiles and some worn furniture, but overall the hotel is spectacular. The breakfast at Stars was amazing.

Reviewed on 14 December 2025

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (606 reviews)
Charming, cozy , clean!

Reviewed on 21 December 2025

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Chatham Wayside Inn
Surfside Inn Chatham

Surfside Inn Chatham

2.5 out of 5
25 Holway St Chatham MA
8/10 Very Good! (159 reviews)
This is a beautiful property very centrally located. I highly recommend the surfside inn.

Reviewed on 15 October 2025

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Surfside Inn Chatham
See all 4,789 properties in Chatham
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.

Discover the most popular places to visit in Chatham

Chatham Lighthouse

Chatham Lighthouse

Learn about the local history of Chatham when you spend time at Chatham Lighthouse. Wander the beautiful beaches and seaside in this trendy area.

Chatham Lighthouse
Enjoy the view, watch the fishing boats come in and unload their catch, and pick up fresh fish or seafood to take home for dinner at the market.

Chatham Fish Pier

After visiting Chatham Fish Pier, make a plan to see the other sights and activities in Chatham. Wander the beautiful beaches and seaside in the area.

Chatham Fish Pier
This windmill, The Godfrey Windmill, in Chase Park has none of its sheets mounted to the vanes. The expression "three sheets to the wind" originated because a windmill with only three sheets deployed will not

Chatham Windmill

Chatham Windmill is just one of the places to see in Chatham, so why not enjoy the other things to explore during your travels? Stroll along the seaside in this trendy area, or check out its seafood restaurants.

Chatham Windmill

Frequently asked questions

How do I find cheap flights to Chatham that have flexible change policies?
When it comes to flying these days, flexibility is a must. That's why we've added a "No change fee" search function to help you find flexible, low-priced tickets to Chatham. It's at the top left of your screen directly below the "Flexible change policies" heading.
Which airlines fly to Chatham?
When you're ready to reserve your airfare to or near Chatham, these top carriers look forward to welcoming you on board:

  • Delta Air Lines - 3,701 flights to or near Chatham each month, including 3,701 flights to Logan Intl. Airport (BOS) per month.
  • JetBlue Airways - 3,407 flights to or near Chatham each month, including 3,407 flights to Logan Intl. Airport (BOS) per month.
  • American Airlines - 2,106 flights to or near Chatham each month, including 2,106 flights to Logan Intl. Airport (BOS) per month.

How can I find cheap tickets to Chatham?
You'll always score a fabulous deal with Expedia, but our "flexible dates" feature makes it that much easier. Enter your preferred flight date, then click on the flexible dates link above to see prices for nearby days. was the cheapest price for a flight to Chatham in the last seven days.
How much is a flight to Chatham?
You could have purchased a return airfare to Chatham from anywhere between and in the last seven days. For one-way journeys leaving from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in Chatham?
Pack your suitcase and touch down at one of these leading Chatham airports:

  • Logan Intl. Airport (BOS) - 12,948 flights per month.
  • Nantucket Memorial Airport (ACK) - 281 flights per month.

When is the cheapest time to fly to Chatham?
Flying on a Tuesday, followed by a Monday, is usually the best way to bag the cheapest deal. Steer clear of the weekend if you can, because Saturday is typically the costliest day. Spend the money you saved having an awesome time in Chatham instead!
How much is a plane ticket to Chatham?
In the last seven days, fares to Chatham cost between and . The early bird catches the worm, so find a cheap flight today.
What months are the cheapest to book a flight to Chatham?
To bag an awesome deal to Chatham, try to book during the month of February when airfares are at their lowest. When do tickets cost the most? In the United States, it's the festive month of December.
How long is a flight to Chatham?
Your flight to Chatham could be short or long depending on where your point of departure is. Before you load up your tablet with movies and audiobooks, have a look at the average flight times for these busy domestic routes:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 48 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 35 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Logan Intl. Airport (BOS) - 1 hour and 25 minutes