Chatham vacation rentals

We found 39 vacation rentals — enter your dates for availability

Discover a selection of 11 homes and other vacation rentals in Chatham that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. Whatever you're looking for, you'll find a rental for everyone's needs, including accessible or non-smoking choices.
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Find out more about Chatham

Find out more about Chatham

Why visit Chatham

  1. Scenic Outdoor Activities: Enjoy beautiful lakes and islands perfect for hiking, biking, and water sports.
  2. Family-Friendly Atmosphere: Chatham offers a welcoming environment ideal for family vacations with various engaging activities.
  3. Charming Village Experience: Stroll through the picturesque streets of Chatham Village, filled with quaint shops and friendly faces.
  4. Variety of Accommodations: Choose from private vacation homes, spacious villas, or cozy cottages for a tailored stay.
  5. Golf Enthusiast's Paradise: Play on stunning golf courses designed for players of all skill levels.

Popular types of accommodation around Chatham

If you’re planning a getaway to Chatham, you’ll find a variety of vacation rentals to suit your needs. The most popular options include charming houses, spacious villas, and inviting cottages. Whether you're searching for a cozy retreat or a comfortable base for your adventures, Chatham offers an array of choices beyond traditional hotels and motels. Enjoy your stay in this beautiful destination with the perfect vacation rental tailored just for you!

  • Houses: The top choice for visitors in Chatham, offering spacious and comfortable accommodations perfect for families or groups.
  • Villas: These stylish and luxurious residences are the second most sought-after option, providing a serene escape.
  • Cottages: Ideal for a quaint and charming stay, these are perfect for guests seeking a cozy atmosphere.
  • Apartments: A practical option for couples or solo travellers, offering convenience in a central location.
  • Condos: A popular choice that combines amenities with a home-like feel, perfect for longer stays.**

Top attractions around Chatham

Chatham in The Villages, Florida, is perfect for outdoor and family vacations, offering attractions like lakes, islands, and golf courses. Visitors can enjoy a scenic experience, with options for fun activities and great local experiences. It's recommended to explore reviews of Chatham vacation rentals and various points of interest to fully appreciate what the area has to offer. Whether you’re travelling solo or with family, Chatham promises memorable adventures.

  1. The Villages Market Square: This vibrant modern square, located 9.7km from Chatham, offers a lively atmosphere with an array of shops, restaurants, and entertainment. Experience the city vibes as you stroll through its charming streets, enjoy live music, and partake in community events.
  2. Nancy Lopez Legacy Golf & Country Club: Situated 1.6km from Chatham, this welcoming golf club features stunning courses and a family-friendly vibe. Enjoy friendly interactions with fellow golfers while appreciating the artful design of the greens.
  3. Florida Horse Park: Located 14.5km from Chatham, this expansive arena provides thrilling equestrian events and family entertainment. It's a great place to experience the excitement of horse shows and engage in various outdoor activities.

Things to do recommended for couples

Planning a romantic getaway in Chatham? Indulge in luxury at Glenview Champions Country Club, enjoy live music at the Orange Blossom Opry, or savour a delightful meal at Cane Garden Country Club. Each spot offers a unique atmosphere perfect for couples seeking unforgettable experiences.

Things to do recommended for families

Families visiting Chatham can enjoy a splashing good time at Wild Waters Theme Park, just 27.4km away, and experience the fun-filled Easy Street Family Fun Center, located 24.1km away, where adventure and excitement await everyone.

Things to do recommended for groups

Explore the vibrant Spanish Springs Town Square, only 8.0km from Chatham, for shopping and dining. Enjoy a round of golf at Stonecrest Country Club, situated 6.4km away, or visit Paddock Mall, 24.1km away, for family fun and entertainment.

What do I need to keep in mind when booking a vacation around Chatham

When planning your trip, whether you're travelling with a group, family, pets, or seeking longer stays, it's essential to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chatham with a group: Think about how many bedrooms you'll require, along with amenities like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Chatham with young kids: Travelling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your location in relation to family-friendly attractions is a wise decision.
  • Taking your pets with you to Chatham: For many, a family getaway isn’t truly fulfilling without their furry companions. If you can relate, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chatham: If you're in search of vacation rentals for a month or longer at great rates, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Chatham

Chatham, located in The Villages, Florida, offers a delightful mix of outdoor activities and family-friendly fun. Explore the charming streets of Chatham Village, relax on the beautiful beaches nearby, and enjoy a quaint atmosphere that is perfect for sports enthusiasts and families alike. With its inviting beach houses and vibrant community, Chatham promises an unforgettable experience filled with sun, sand, and friendly faces.

  • Calumet Grove: Calumet Grove is a charming neighborhood located 1.3km away from Chatham, offering a delightful blend of outdoor activities and family-friendly experiences. This area is perfect for those who enjoy sports, particularly golf, as it features a private country club and a well-maintained golf course. The surrounding landscape includes beautiful lakes, a nature reserve, and nearby beaches, making it an ideal spot for relaxation and outdoor adventures. Whether you’re hitting the greens or taking a leisurely stroll along the lake, Calumet Grove promises a memorable escape.
  • Piedmont: Situated 1.6km from Chatham, Piedmont is a vibrant neighborhood that is perfect for outdoor enthusiasts and families. Visitors can enjoy a variety of activities, including golf at the local country club and shopping in nearby retail areas. The proximity to a stunning nature reserve and inviting beaches enhances the travel experience, providing ample opportunities for picnicking, hiking, or simply enjoying a day by the river. Piedmont's charming atmosphere and recreational options make it a must-visit during your vacation.
  • Briar Meadow: Briar Meadow is another delightful neighborhood located 1.6km from Chatham, offering a similar focus on outdoor activities and family fun. This area is well-known for its excellent golf courses and private country club, attracting sports enthusiasts and casual players alike. Nature lovers will appreciate the nearby nature reserve, picturesque lakes, and serene rivers that provide a peaceful backdrop for exploration and relaxation. The inviting environment and recreational offerings of Briar Meadow make it an excellent choice for visitors seeking a wholesome getaway.

Best time to go to Chatham

If you're planning a trip to Chatham, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs from January to March, while off-peak times, like May and August to September tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January58.3°F (14.6°C)Light RainMostly SunnyModerately HighAverage
February62.4°F (16.9°C)Light RainMostly SunnyModerately HighSlightly High
March66.0°F (18.9°C)Light RainMostly SunnyModerately HighSlightly High
April71.6°F (22.0°C)Light RainMostly SunnyAverageAverage
May76.5°F (24.7°C)Light RainMostly SunnyModerately LowAverage
June80.6°F (27.0°C)Light RainMostly SunnyAverageAverage
July81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
August81.7°F (27.6°C)Light RainMostly SunnyModerately LowSlightly Low
September79.3°F (26.3°C)Light RainMostly SunnyModerately LowSlightly Low
October73.6°F (23.1°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
November66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
December62.2°F (16.8°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for an extended stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your needs!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient area for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved or reserved properties are now neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chatham?
According to our data, houses are the most popular vacation property type in Chatham. But naturally, everyone’s idea of an epic trip will differ. Vrbo has vacation homes with every size, shape and budget in mind, and we’ll help you find your ideal match.
How much does it cost to rent a vacation rental in Chatham?
Length of stay, property type and time of year are some factors that can determine the price of a vacation home. Simply add your dates of travel to find your ideal fit. From cozy cabins to plush villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Chatham?
The average price for a vacation rental close to the beach in Chatham will depend on when you’ll be there and the size and style of property you’re searching for. You can find prices easily and quickly on Vrbo by entering your destination and preferred travel dates. Then use the filter tool to pick the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.
Are there pet-friendly vacation rentals in Chatham?
Pack a squeezy toy and a bone for your beloved pooch because Chatham has 10 vacation homes that put out the welcome mat to pets. Let your furriest pal have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and dates, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Chatham?
Pack your swimming gear and swim ring, because there are 10 houses with a private pool in Chatham. Unwind at one of these sought-after vacation homes and let every day be a pool day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find a place to make a splash!
What are popular rental amenities in Chatham?
When it comes to rental amenities that guests are looking for in Chatham, tennis, a barbecue grill and nearby museums are at the top of the list. With Vrbo vacation homes, you’ll find options to match your taste and style, whether you’re planning to get away with relatives, friends or even pets.
Are there large group vacation rentals in Chatham?
There are two vacation rentals in Chatham that can accommodate a group of five or more people. From family trips to events like a friend’s birthday, these stays have ample room to chill out with the people you love.
Are there vacation rentals in Chatham that welcome kids?
Gather your whole family for an epic adventure in Chatham at one of our 10 family-friendly properties. These stays come with conveniences that are ideally suited to getaways with children, like laundries, extra bedrooms and pools. Just check the “Properties good for families” filter and pick your favorite.
What are the top attractions for families in Chatham?
If you’ve got the little ones in tow, include these family-friendly attractions in Chatham on your list of things to do:

  • The Villages Market Square
  • Nancy Lopez Legacy Golf & Country Club

Can I find two-bedroom vacation rentals in Chatham?
Take your pick of seven two-bedroom vacation properties in Chatham. Settle the kids into the second room or fill it with a couple of your best buddies. There’s ample space for whoever’s fortunate enough to be joining your journey.
Are there vacation rentals with WiFi in Chatham?
Chatham has four vacation rentals with WiFi, so you can stay connected during your trip. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movie blockbusters to scrolling social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Chatham?
You’ll have a choice of 10 Vrbo vacation homes with air conditioning in Chatham giving you that cooling breeze and extra level of comfort. Simply enter your travel dates and then make use of our filters to look for stays with air conditioning.
How old do you have to be to rent a vacation rental in Chatham?
We recommend you check with the Chatham vacation home you’re considering on Vrbo as age restrictions vary. However, it’s typically 16, 18 or 21.
How long can I rent a vacation rental in Chatham for?
How long you can rent a vacation rental in Chatham varies according to the property. Just enter your preferred travel dates to look at a list of options offering extended stays. With many amenities like full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to find the perfect place to call your home away from home in Chatham.

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