Chatham Trips (flight + hotel)

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Top hotels in Chatham

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is P5,712 per night from 1 May to 2 May
P5,712
per night
1 May - 2 May
9/10 Wonderful! (230 reviews)
Loved it!
"This place is so cute! My husband, my toddler and our Yorkie had a great night stay. You can check in on a kiosk and text them for anything you need! Everyone was so friendly and being pet friendly was a big bonus! Bit of a misunderstanding on my part, no complimentary breakfast."

Reviewed on Apr 27, 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is P6,301 per night from 20 May to 21 May
P6,301
per night
20 May - 21 May
8.8/10 Excellent! (868 reviews)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion."

Reviewed on Apr 13, 2024

The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is P5,836 per night from 6 May to 7 May
P5,836
per night
6 May - 7 May
8.8/10 Excellent! (1,004 reviews)
Black Swan Inn a gem!
"Great visit to The Black Swan Inn. Perfectly located central to activities in the Berkshires. Fantastic customer service and very clean."

Reviewed on Apr 28, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 much does a Chatham vacation package cost?
Get your credit card ready, because a trip to Chatham starts from an enticing . When you combine your flights, hotels and car rentals into a package, you’ll land the lowest prices.
How do I get a cheap travel package to Chatham?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we’ve got them all. Pick and choose the combination that suits you and watch your savings grow. We know a travel package is never a one-size-fits-all. That’s why we offer over 550 partner airlines and 1,000,000 hotels worldwide, which lets you customize your Chatham adventure.
Where should I stay in Chatham?
There’s so much to explore in Chatham, so spend your nights close to its top sights and allow yourself more time sightseeing. The Mac-Haydn Theatre is one place to add to your to-do list.
What are the top hotels in Chatham?
When it comes to comfortable and convenient places to stay in Chatham, you can’t beat Charming Farm House On 460 Acre Working Farm. Look up our offers and score a bargain.
How far in advance should I book my Chatham vacation?
It depends on the air carrier, but you can generally compare international airfares on Expedia up to 12 months in advance. While it’s a good idea to book ahead of time, lucky customers occasionally score a cheaper flight just weeks before departure dates.
What does an Expedia Chatham travel package include?
That depends entirely on you. You can pick from a variety of Chatham bundles, such as a rental car, flight and hotel. You can also book a hotel and a flight, or a rental car and a flight. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your dream Chatham trip looks like, you’ll save!
What should I know before booking a Chatham travel package?
Discover deals to match your budget with an Expedia package. Hotels, flights, rental cars — we have everything you need to plan your break. You’ll save loads just by bundling your bookings. Whether you’re going on an adventure in the snow or sunning yourself on a warm beach, your ideal vacation is only a few clicks away.
Can I choose my airline with a Chatham Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Chatham vacation package?
Yes, you can. We realize life doesn’t always go to plan, so we’re here to help if you have to make changes to your Chatham vacation package. It may be possible to cancel or change your itinerary at no cost if you’ve booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.