Chatham Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SAR 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 SAR 1,839 per night from May 17 to May 18
SAR 1,839
SAR 2,104 total
17 May - 18 May
includes taxes & fees
9.2/10 Wonderful! (825 reviews)
window and door were not closing all the way, got noise complaint after daughter became ill. Food was good staff ok

Reviewed on 13 May 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is SAR 875 per night from May 25 to May 26
SAR 875
SAR 1,164 total
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (669 reviews)
We had a very relaxing stay. The breakfast was great and liked that it varied a little every day. The staff was very courteous. Everything from the room to the pool and fitness center were very clean!

Reviewed on 12 May 2026

Chatham Wayside Inn
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
The price is SAR 999 per night from Jun 2 to Jun 3
SAR 999
SAR 1,143 total
2 Jun - 3 Jun
includes taxes & fees
8.8/10 Excellent! (238 reviews)
Great breakfast, nice pool area

Reviewed on 7 November 2025

Queen Anne Inn
See all 4,929 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.

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