Chatham Vacations from $228

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Your Chatham Vacation

Book one of our vacation packages to Chatham and immerse yourself in the charms of this interesting neighborhood. Especially known for its golfing, your next epic adventure begins right here. Love to take in the sights? Nancy Lopez Legacy Golf & Country Club and Glenview Champions Country Club are two nearby attractions to visit during your trip to Chatham. Whatever your ideal Chatham vacation may look like, you can turn it into reality with Expedia.

The Latest Chatham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

3.5 out of 5
Vilano Beach
Save 100% on your flight
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (540 reviews)
Nice Beach across the road, Very nice staff!

Reviewed on Jul 6, 2025

ette hotel

ette hotel

5 out of 5
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.8/10 Exceptional! (310 reviews)
very friendly helpful staff. nice area with many restaurants and grocery stores around. clean rooms. elegant hotel

Reviewed on Jul 4, 2025

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (354 reviews)
Nice place. Kids had a good time. Not encouraged to go there if you are a minority. You wont feel welcomed. The staff is great, but the type of people that go there arent really folks that likely share the same interests as you do. There are Confederate flags all over; etc. Hotel rooms are no bueno, old. IF you want something nice, you need to spend the money glamping or have your own trailer.

Reviewed on Jun 24, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
7.8/10 Good! (1,644 reviews)
Every single thing is awesome ❤️

Reviewed on Jul 6, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,274 reviews)
The property was nice, lots of things to do for everyone. However the shipwreck water park wasn’t included you have to pay for that separately. Also, be prepared to pay additional resort fees at the property.

Reviewed on Jul 11, 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
4.5/5(30 area reviews)

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

Get rates
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
$91 nightly
The price is $101 total per night from Jul 15 to Jul 16
$101 total
Jul 15 - Jul 16
Total includes taxes and fees
8.8/10 Excellent! (1,519 reviews)
Great Beds, Good for Families and affordable!
"The front staff person was very nice and friendly. Gave us a list of times for cookies, check out, and breakfast. The room was spacious and the beds were very comfortable. The air conditioner worked really well, almost too cold, LOL. The only thing wrong was the TV didn't work very well for my 9 ..."

Reviewed on Jul 9, 2025

Equus Inn Ocala
Best Western Ocala Park Centre
Best Western Ocala Park Centre
2.5 out of 5
3701 SW 38th Avenue, Ocala, FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $80 total per night from Jul 15 to Jul 16
$80 total
Jul 15 - Jul 16
Total includes taxes and fees
8.2/10 Very Good! (1,172 reviews)
Great stay
"Quick overnight stay with family on way to Port Canaveral. Clean, fairly priced, quiet, and we loved the Cracker Barrel next door! And service was excellent and very helpful. My daughter left something in the room when we left and we were able to go back and retrieve it five days later on our way ..."

Reviewed on Jul 12, 2025

Best Western Ocala Park Centre
See all 2,213 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Discover the most popular places to visit in Chatham

The Villages Market Square

4.5/5(174 reviews)

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

Nancy Lopez Legacy Golf & Country Club

Enjoy a round of golf in The Villages at Nancy Lopez Legacy Golf & Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Nancy Lopez Legacy Golf & Country Club

Glenview Champions Country Club

Enjoy a round of golf in The Villages at Glenview Champions Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Glenview Champions Country Club

Things to do

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

$55
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.