Chatham Vacations from $567

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Your Chatham Vacation

Planning your next big adventure is a breeze with a Chatham vacation package. The neighborhood of Lovell, which is great for walking, makes a terrific base to uncover the delights of this lively city. Like some inspiration on what to see or do first during your trip to Chatham? Head for major attractions like Baldface Range. A couple of clicks is all it takes to build the ultimate Chatham vacation on Expedia.

The Latest Chatham vacation packages

Price found within the past 48 hours. Click for updated prices.
Old Stagecoach Inn

Old Stagecoach Inn

3 out of 5
Price was $703, price is now $567 per person
$567
per person
Apr 10 - Apr 13
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Burlington (BTV)
9.4/10 Exceptional! (365 reviews)
Very nice stay. The owner was a very nice lady. We enjoyed our stay.

Reviewed on Jan 8, 2026

Outbound Stowe

Outbound Stowe

3.5 out of 5
Price was $1,088, price is now $851 per person
$851
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Burlington (BTV)
9/10 Wonderful! (260 reviews)
Clean, nicely decorated and very comfortable. Great location.

Reviewed on Feb 1, 2026

Blind Tiger Burlington

Blind Tiger Burlington

3.5 out of 5
South End
Price was $920, price is now $722 per person
$722
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Burlington (BTV)
9.4/10 Exceptional! (222 reviews)
Staff, clean room , location

Reviewed on Jan 1, 2026

Green Mountain Inn

Green Mountain Inn

3.5 out of 5
Stowe Village Historic District
Price was $1,079, price is now $861 per person
$861
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Burlington (BTV)
9.4/10 Exceptional! (1,002 reviews)
Great pool and hot tub and excellent location

Reviewed on Feb 3, 2026

Bluebird Cady Hill Lodge

Bluebird Cady Hill Lodge

3 out of 5
Price was $1,049, price is now $846 per person
$846
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Burlington (BTV)
9.2/10 Wonderful! (611 reviews)
Room was spotless, desk was super friendly. We were late for the Stowe Stowe surf club but we will make it back.

Reviewed on Jan 13, 2026

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Discover the most popular places to visit in Chatham

Sherman Farm

You can learn about the history of Center Conway with a trip to Sherman Farm. Make time for the shops and ski slopes in this romantic area.

Sherman Farm

Chatham Hotel Deals

North Conway Grand Hotel

North Conway Grand Hotel

4 out of 5
72 Common Court North Conway NH
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $145 total per night from Mar 4 to Mar 5
$145 total
Mar 4 - Mar 5
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Great place

Reviewed on Jan 31, 2026

North Conway Grand Hotel
Cambria Hotel North Conway

Cambria Hotel North Conway

3 out of 5
1858 White Mountain Highway North Conway NH
Fully refundable
$105 nightly
The price is $114 total per night from Feb 10 to Feb 11
$114 total
Feb 10 - Feb 11
Total with taxes and fees
8.8/10 Excellent! (486 reviews)
Staff was wonderful; clean room;

Reviewed on Jan 26, 2026

Cambria Hotel North Conway
Town and Country Inn & Resort

Town and Country Inn & Resort

2.5 out of 5
20 State Route 2 Gorham NH
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $99 total per night from Feb 16 to Feb 17
$99 total
Feb 16 - Feb 17
Total with taxes and fees
8.8/10 Excellent! (1,039 reviews)
Room was clean, Bathroom spotless! Has a lounge/Bar and a restaurant! Temperature was -5 degrees out so I hit the hot tub! Its an old Motel up in the Hills of NH, very well taken care of and I will stay again!

Reviewed on Jan 29, 2026

Town and Country Inn & Resort
See all 2,944 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.

Find the Best Chatham Vacation Packages

Chatham Essential Information

Language
English
Currency
U.S dollars
Top Sights
Baldface Range and Sherman Farm

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Frequently asked questions

How much does a Chatham vacation package cost?
Offering excellent value package deals from $567 on Expedia, you'll be pleasantly surprised at how much a vacation to Chatham costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chatham?
October, November and December are great times to search for cheap Chatham vacation packages. Traveling in less busy periods means you can generally find reduced prices on accommodations and flights.
How many days is enough for Chatham?
With a well-planned schedule, you can easily hit the most popular Chatham attractions in a few days. But if you'd like to discover hidden gems or go on day tours, think about booking your Chatham vacation for longer.
How to find the best Chatham package deals?
Bagging a cheap Chatham package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Chatham package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Chatham vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Chatham vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chatham?
Score incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chatham vacation.
Does Expedia offer Book Now, Pay Later Chatham vacation packages?
Your Chatham break is meant to be an escape from your daily routine, not a reason for money-related stress. So to give you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.