Owner Direct Vacation
Rentals in Chatham
The Best Owner Direct Vacation Rentals in Chatham. Explore thousands of vacation home rentals, large cabins, and villas near Chatham
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Explore the Best Chatham Vacation Homes
Looking for the perfect place to stay in Chatham? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chatham character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Chatham Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Chatham
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Wednesday Feb 25
Chatham, The Villages
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Chatham vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Chatham
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How to Reserve Your Chatham Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Chatham Vacation Rental FAQs
1. What are the top vacation rentals in Chatham?
There are a lot of options in Chatham. If you plan on staying in the Chatham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chatham:
- Close to 2 squares and Glenview Country Club
- The Coconut Courtayrd-Private Pool& Tiki Hot Tub-Minutes From Fun-Walk 2 Golf
- Beautifully Refurbished villa in an exciting active retirement community.
- The Villages FL Community w/Elec. Golf Cart. Restaurants, Shopping & Hospitals.
- Summerfield Home w/Pool & Hot Tub!
- Well appointed home welcomes you PLEASE NOTE: We are outside of The Villages
- Beautiful Golf Front 3-2. All New Inside ! Cable , WI-FI and Golf Cart !
- Beautiful, updated, private, contemporary “beachy” Guest suite
- Private Heated Pool & Hottub - Pet Friendly- Close to L Sumpter & Spanish Spring
- Cheerful 3 bedroom home with free parking.
2. How many vacation rentals have private pools in Chatham?
There are 13 vacation rentals with private pools near Chatham. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Chatham are best for families?
If you are looking for a family-friendly vacation home in Chatham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chatham:
4. How many vacation rentals are available in Chatham?
Currently, the total number of properties listed in 2026 is over 322 in the Chatham area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chatham.