Chatham holiday homes

We found 45 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Chatham that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Chatham

  • Stunning natural beauty: Chatham features picturesque lakes and scenic islands, perfect for relaxation and exploration.
  • Family-friendly activities: Ideal for family vacations, with a range of outdoor adventures suitable for all ages.
  • Chatham Bay Beach: A beautiful spot for sunbathing and enjoying water activities with loved ones.
  • Charming local community: Experience the warmth of friendly locals while immersing yourself in rural Chatham's charm.
  • Variety of sports: Engage in a range of recreational activities, from golf to beach fun, ensuring a memorable holiday.

Top attractions near Chatham

Chatham, located in The Villages, Florida, is perfect for outdoor and family vacations, featuring stunning lakes, islands, and golf courses. Visitors can enjoy Chatham Bay Beach and explore the scenic Chatham Islands, making it an ideal spot for those seeking relaxation and adventure. Consider local vacation rentals for a comfortable stay while immersing yourself in the beautiful surroundings.

  • Lake Weir: A stunning lake 11.3km from Chatham, perfect for a romantic day out. Enjoy its beautiful beach and picturesque scenery, ideal for outdoor activities and relaxation.
  • Nancy Lopez Legacy Golf & Country Club: Located just 1.6km away, this family-friendly golf course offers a welcoming atmosphere. Ideal for golf enthusiasts and families looking to enjoy a round together.
  • The Villages Market Square: A vibrant modern square 9.7km from Chatham, bustling with city vibes, great shops, and lively entertainment, perfect for an afternoon stroll or evening out.

Things to do recommended for couples

For a romantic getaway in Chatham, unwind at the Glenview Champions Country Club for a touch of luxury, enjoy lively performances at the Orange Blossom Opry, or indulge in a lovely meal at Cane Garden Country Club, surrounded by charming vibes perfect for couples.

Things to do recommended for families

Families in Chatham can have a blast at Easy Street Family Fun Center, an arcade and adventure zone located 24.1km away. It's a fantastic spot for kids to enjoy games and activities, creating memorable experiences in a lively, family-friendly atmosphere.

Things to do recommended for groups

Explore Spanish Springs Town Square for a vibrant shopping experience, enjoy a round of golf at Stonecrest Country Club, or visit Paddock Mall for a mix of entertainment and shopping. Each location offers unique vibes perfect for your group adventure in Chatham.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're heading off on a trip with friends, family, pets, or planning an extended stay, it's important to prioritise your needs when filtering options. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Chatham with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group get-togethers. Luckily, you can narrow down your options for all these criteria and more on Vrbo.
  • Traveling to Chatham with young kids: Taking a trip with young kids can be quite tricky. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to Chatham: For many families, a holiday wouldn’t feel complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Chatham: If you’re on the hunt for holiday rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Chatham

Chatham, nestled in The Villages, offers a delightful blend of family-friendly activities and outdoor adventures. Explore the nearby Chatham Island for stunning landscapes, or venture to the nearby sand dunes for some fun in the sun. With its friendly locals and recreational options, this vibrant neighbourhood is perfect for a memorable family holiday. Experience the charm of rural Chatham while enjoying a variety of sports and leisure activities that the whole family will love.

  • The Villages: The Villages is a vibrant city that offers a blend of family-friendly activities and outdoor experiences. Nestled in the heart of Florida, it invites visitors with its well-planned shopping areas and numerous golf courses. The proximity to local landmarks like beautiful beaches and theme parks enhances the travel experience. With a strong community feel, The Villages is perfect for those looking to enjoy leisurely strolls, family outings, and engaging in various recreational activities.
  • Piedmont: Just one mile from Chatham, Piedmont is a charming neighborhood known for its outdoor and sports experiences. Visitors can enjoy activities at the local country private club and explore nearby shopping areas. Piedmont’s appeal is further enhanced by attractions like film studios and a lovely beach, making it an ideal spot for families. Whether you’re keen on a round of golf or a relaxed day out, Piedmont offers a delightful blend of leisure and adventure.
  • Summerfield: Located three miles from Chatham, Summerfield is a picturesque city that captures the essence of outdoor and romantic experiences. Surrounded by scenic landscapes, visitors can indulge in golfing at local courses or enjoy the tranquil beauty of nearby lakes and rivers. Summerfield is perfect for couples seeking a romantic getaway or anyone looking to connect with nature. With its charming town neighbourhoods and stunning views, it’s an inviting destination for relaxation and exploration.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January58.3°F (14.6°C)Light RainMostly Sunny
February62.4°F (16.9°C)Light RainMostly Sunny
March66.0°F (18.9°C)Light RainMostly Sunny
April71.6°F (22.0°C)Light RainMostly Sunny
May76.5°F (24.7°C)Light RainMostly Sunny
June80.6°F (27.0°C)Light RainMostly Sunny
July81.7°F (27.6°C)Light RainMostly Sunny
August81.7°F (27.6°C)Light RainMostly Sunny
September79.3°F (26.3°C)Light RainMostly Sunny
October73.6°F (23.1°C)No Rain (Dry)Mostly Sunny
November66.2°F (19.0°C)Light RainMostly Sunny
December62.2°F (16.8°C)Light RainMostly Sunny

Booking with Vrbo is a breeze

Are you keen to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. You can also enjoy noteworthy savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of accommodation. We're here to help you find the perfect spot for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a convenient way to plan your next adventures, pick up where you left off, or manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Chatham for a holiday rental?
The best time to visit Chatham for a holiday rental is during the peak season from February to April. This period attracts travellers eager to enjoy the pleasant weather and vibrant setting, making it ideal for outdoor activities such as boating, fishing, and exploring the beautiful coastal scenery. With temperatures generally ranging from the mid-teens to low 20s Celsius, visitors can comfortably enjoy the sun and partake in various sightseeing opportunities.September is particularly popular in Chatham, as it offers a lovely transition into autumn, with fewer crowds and warm temperatures. This month is superb for those who appreciate a more relaxed vibe while still soaking up the area's charm. You'll find plenty of local events and the chance to explore stunning beaches and nature trails.For those looking to save a bit, October is a wonderful option to consider. During this quieter month, you can still enjoy pleasant weather while experiencing the natural beauty of Chatham without the hustle and bustle of peak season.
Are all fees included in the Chatham holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chatham holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Chatham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chatham holiday homes?
You can find great discounts on holiday homes in Chatham on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chatham holiday home booking on Bookabach?
To find Chatham holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chatham?
A long-stay holiday home in Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chatham holiday home?
Book your Chatham holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chatham?
Prices for holiday homes in Chatham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chatham to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas