Chatham Vacation Packages

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Top Holiday Package Deals in Chatham

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
per person
Oct 20 - Oct 27
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.4/10 Very Good! (1,341 reviews)
The management team and staff were great! They are doing a fantastic job maintaining the property.

Reviewed on Jul. 29, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
Great place to stay will be back, updated furniture very clean

Reviewed on Jul. 29, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
While I did like this property and enjoyed my stay, I believe the water park should be free for guest since it’s just a lazy pool, wave pool and 2 waters slides. I don’t think the price to enter the water park was worth it. I was also disappointed that the windows did not have shades that could be lowered, just blinds. The blinds left space on the sides where others could see out and in. I had to use a towel to block the space to provide privacy.

Reviewed on Jul. 29, 2025

ette hotel

ette hotel

5 out of 5
per person
Sep 30 - Oct 6
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
Fantastic hotel. Beautiful room, great food, exceptional staff and the smell was phenomenal

Reviewed on Jul. 27, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
I liked everything about the property; however I did not get a balcony as it stated in my confirmation email and upon booking. I also did not like that the times available for the waterpark did not meet me needs at all, and it was closed as well as the pool whenever i wanted to go. I had a relative that stayed at the Westgate in Orlando, and their pool was open until 11pm and I enjoyed her balcony as I did not get one.

Reviewed on Jul. 22, 2025

Where to stay in Chatham

Find the best Chatham areas and neighborhoods for the activities you enjoy most. Learn more about Chatham
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Lake Sumter Landing

1 out of top 10 points of interest in this area

Though Lake Sumter Landing might not have many top sights, you can venture to the surrounding area to see attractions like The Villages Market Square and Cane Garden Country Club.

Find hotels in Lake Sumter Landing

Chatham Hotel Deals

Sunny Home in The Villages w/ Lanai & Pool Access!

Sunny Home in The Villages w/ Lanai & Pool Access!

The Villages
7.4/10 Good! (13 reviews)
Chatham Villa
"Loved the Villa, the Tv was terrible. Could only watch Sling Free, with commercials every 3 minutes. The DVD was not hooked up and there wasn’t a Magnavox remote anywhere. So we were lucky had kindles. Therefore., we would not rent the Villa again."

Reviewed on Apr. 9, 2025

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Sunny Home in The Villages w/ Lanai & Pool Access!
Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
3434 Sw College Rd, Ocala, FL
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,545 reviews)
"Very nice place, I'm sure it won't be the last time."

Reviewed on Jul. 27, 2025

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Equus Inn Ocala
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive, The Villages, FL
The price is CA $172 per night from Aug 3 to Aug 4
CA $172
CA $184 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,194 reviews)
"Very accommodating staff. Great location. Slept very well."

Reviewed on Jul. 27, 2025

The Waterfront Inn
See all 2,222 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.
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Frequently asked questions

How much does a Chatham vacation package cost?
Starting from just CA $621, a package is your passport to affordable travel. Put together your Chatham adventure by picking from our huge range of hotels, flights and rental cars.
How do I get a cheap travel package to Chatham?
Crafting your own Chatham vacation package with Expedia is such a simple way to save. We offer access to over 550 airlines and 1,000,000 hotels all over the world. With such an awesome range to pick from, you'll have no issues pulling together your dream vacation.
Where should I stay in Chatham?
If you hope to check out Nancy Lopez Legacy Golf & Country Club, skip commuting and stay nearby. It's one of the best attractions in the area.
What are the top hotels in Chatham?
Whether you're planning to stay for one night or one week in Chatham, you'll get a wonderful night's rest at Sunny Home In The Villages With Pool Access. This option is popular with lots of travelers.
How far in advance should I book my Chatham vacation?
To bag discount prices, book as early as you can. Air carriers typically release flight tickets, along with some of the lowest fares, up to a year prior to departure. Hotels, car rental and activities should also be booked early to avoid disappointment. If you were hoping for a last-minute getaway in Chatham, there are always plenty of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Chatham travel package include?
From hotels and flights to rental cars, Expedia can help you shape a Chatham package that's right for you. Vacationing for a week or two? Consider a hotel, flight and rental car bundle. If you can only manage a quick getaway, a hotel and airfare deal could be more your style. Experiences can also be added after you've booked. Our vacation packages make it easy to plan and save.
What should I know before booking a Chatham travel package?
Tailor deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we've got everything you need to plan your getaway. You'll save precious cash just by combining your bookings. Whether you're going on a skiing adventure or sunning yourself on a warm beach, your dream getaway is only clicks away.
Can I choose my airline with a Chatham Expedia vacation package?
You certainly can. We offer more than 550 partner airlines throughout the world, so go with the carrier that's a good fit for your budget and travel needs.
If I'm not able to travel, can I cancel my Chatham vacation package?
Don't worry if you're rethinking your Chatham vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We totally understand life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that happens. When you're ready to make changes, we're here to help.

Discover the most popular places to visit in Chatham

The Villages Market Square

You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.

The Villages Market Square

Things to do

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

CA $75
per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in The Villages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.