Chatham Vacations from $248

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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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $580, price is now $248 per person
$248
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (3,229 reviews)
Clean nice staff ❤️❤️❤️

Reviewed on Dec 5, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $892, price is now $370 per person
$370
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (2,232 reviews)
Visited the Florida Black Friday weekend. The proximity to the Florida mall makes it a great location for shopping. This is a huge mall with a large assortment of shops. We were impressed with the cleanliness in the hotel and the mall. Our room was clean and quiet. The bed was very comfortable. Crickets restaurant is in the hotel. They have a good assortment of meal and drink options. The waiters were very accommodating and attentive. The sun shone the afternoon we were there so we enjoyed the beautiful outdoor pool and hot tub. We would definitely stay at the Florida hotel again in the future.

Reviewed on Dec 3, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $762, price is now $327 per person
$327
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,085 reviews)
Loved it. Very clean and felt safe

Reviewed on Nov 30, 2025

Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Price was $889, price is now $408 per person
$408
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,549 reviews)
Great place. Well managed. Comfortable. Good location

Reviewed on Dec 5, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,578, price is now $748 per person
$748
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
No Beach view but beach is an10m walk so not too bad. Beach chairs falling apart. The pools and tiki bar were awesome. The two room suite was okay and for the most part pretty clean. But there were some dead bugs which is not what I expected for the price point.

Reviewed on Nov 6, 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

Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
3434 Sw College Rd Ocala FL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Dec 7 to Dec 8
$90 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,738 reviews)
The room was spotless, Free Breakfast was amazing, heated pool!

Reviewed on Dec 1, 2025

Equus Inn Ocala
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
$119 nightly
The price is $127 total per night from Dec 11 to Dec 12
$127 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (1,273 reviews)
Great hotel

Reviewed on Dec 1, 2025

The Waterfront Inn
Howard Johnson by Wyndham Ocala FL I-75

Howard Johnson by Wyndham Ocala FL I-75

3 out of 5
3951 NW Blitchton Road Ocala FL
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $65 total per night from Dec 7 to Dec 8
$65 total
Dec 7 - Dec 8
Total with taxes and fees
6.6/10 (1,014 reviews)
Great service

Reviewed on Dec 1, 2025

Howard Johnson by Wyndham Ocala FL I-75
See all 2,423 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.