Chatham Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Chatham

Comfort Inn Glenmont - Albany South
Comfort Inn Glenmont - Albany South
2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundableReserve now, pay when you stay
The price is S$140 per night from 8 Dec to 9 Dec
S$140
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (895 reviews)
"Great spot and just 8 minutes to downtown Albany. I had a good night sleep 😴 enjoy"

Reviewed on 21 Nov,2024

Comfort Inn Glenmont - Albany South
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 S$180 per night from 26 Nov to 27 Nov
S$180
includes taxes & fees
26 Nov - 27 Nov
9/10 Wonderful! (442 reviews)
"Staff were very friendly and the rooms were decorated adorably! We absolutely enjoyed our stay!"

Reviewed on 20 Nov,2024

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is S$141 per night from 1 Dec to 2 Dec
S$141
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,001 reviews)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious."

Reviewed on 18 Nov,2024

The Yankee, Trademark Collection by Wyndham
See all 1,488 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 much does a Chatham holiday 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 holiday?
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 holiday is only a few clicks away.
Can I choose my airline with a Chatham Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines worldwide. Our holiday 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 holiday package?
Yes, you can. We realise life doesn’t always go to plan, so we’re here to help if you have to make changes to your Chatham holiday 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.