Discover Your Perfect Chessy Vacation Homes

Best Vacation Homes in Chessy

10.0
Exceptional
(9 Reviews)
753 ft² 6 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
R2,326/Night For 7 Nights R16,281
10.0
Exceptional
(3 Reviews)
1506.95 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Free Cancellation House
  • Pet Friendly
  • Parking
  • Internet
R6,015/Night For 7 Nights R42,108
9.8
Exceptional
(107 Reviews)
1 Bedroom 1 Bathroom
Family Friendly Bed & Breakfast
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
R1,876/Night For 7 Nights R13,127
10.0
Exceptional
(2 Reviews)
474 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Pool
  • Balcony/Terrace
  • Kitchen
R1,972/Night For 7 Nights R13,800
10.0
Exceptional
(3 Reviews)
807.29 ft² 6 Guests 1 Bedroom 1 Bathroom
Free Cancellation House
  • Fireplace/Heating
  • Balcony/Terrace
  • View
R1,786/Night For 7 Nights R12,502
10.0
Exceptional
(1 Review)
484 ft² 3 Guests 1 Bedroom 1 Bathroom
Ocean View House
  • Fireplace/Heating
  • Ocean View
  • Balcony/Terrace
R1,361/Night For 7 Nights R9,529
9.0
Exceptional
(2 Reviews)
431 ft² 4 Guests 1 Bedroom 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Breakfast
R2,018/Night For 7 Nights R14,129
8.0
Excellent
(1 Review)
215 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
R974/Night For 7 Nights R6,818

Chessy Luxury Rentals

10.0
Exceptional
(1 Review)
4951 ft² 29 Guests 10 Bedrooms 9 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
R39,580/Night For 7 Nights R277,059
New
34 Guests 11 Bedrooms 7 Bathrooms
Pet Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Air Conditioner
R28,255/Night For 7 Nights R197,789
New
2690.98 ft² 15 Guests 6 Bedrooms 6 Bathrooms
Family Friendly House
  • Pool
  • Balcony/Terrace
  • Parking
R24,539/Night For 7 Nights R171,766
New
13 Guests 5 Bedrooms 2 Bathrooms
Group Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
R21,894/Night For 7 Nights R153,250
9.0
Exceptional
(1 Review)
5381.95 ft² 14 Guests 5 Bedrooms 4 Bathrooms
Free Cancellation Villa
  • Pool
  • Balcony/Terrace
  • View
R20,322/Night For 7 Nights R142,259
10.0
Exceptional
(2 Reviews)
5920 ft² 30 Guests 8 Bedrooms 8 Bathrooms
Family Friendly Cottage
  • Private Pool
  • Fireplace/Heating
  • Pool
R19,617/Night For 7 Nights R137,314
New
14 Guests 5 Bedrooms 5 Bathrooms
Family Friendly House
  • Private Pool
  • Hot Tub
  • Spa
R19,348/Night For 7 Nights R135,441
New
3122 ft² 15 Guests 6 Bedrooms 6 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
R19,131/Night For 7 Nights R133,913

Chessy Pet Friendly Vacation Rentals

New
4 Guests 2 Bedrooms 1 Bathroom
Couples Retreat House
  • Fireplace/Heating
  • Pet Friendly
  • Internet
R2,375/Night For 7 Nights R16,626
9.5
Exceptional
(152 Reviews)
172.22 ft² 2 Guests 1 Bedroom 1 Bathroom
Free Cancellation Bed & Breakfast
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R1,692/Night For 7 Nights R11,845
10.0
Exceptional
(8 Reviews)
1830 ft² 12 Guests 5 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
R10,805/Night For 7 Nights R75,639
9.5
Exceptional
(132 Reviews)
258.33 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Ocean View Bed & Breakfast
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R1,577/Night For 7 Nights R11,040
10.0
Exceptional
(2 Reviews)
980 ft² 7 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Balcony/Terrace
  • Pet Friendly
  • Kitchen
R2,017/Night For 7 Nights R14,129
9.8
Exceptional
(6 Reviews)
1851 ft² 11 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Balcony/Terrace
  • Pet Friendly
  • Kitchen
R13,461/Night For 7 Nights R94,221
8.0
Excellent
(1 Review)
2476 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
R8,894/Night For 7 Nights R62,266
New
2153 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Pool
  • Balcony/Terrace
  • Pet Friendly
R12,678/Night For 7 Nights R88,750

Chessy Large Vacation Homes

10.0
Exceptional
(1 Review)
1507 ft² 13 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Balcony/Terrace
  • Kitchen
  • Parking
R3,845/Night For 7 Nights R26,911
9.3
Exceptional
(209 Reviews)
344.44 ft² 7 Guests 5 Bedrooms 2 Bathrooms
Free Cancellation House
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
R2,097/Night For 7 Nights R14,688
10.0
Exceptional
(1 Review)
4951 ft² 29 Guests 10 Bedrooms 9 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
R29,764/Night For 7 Nights R208,353
8.0
Excellent
(1 Review)
2583 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
R9,508/Night For 7 Nights R66,554
9.3
Exceptional
(5 Reviews)
269.1 ft² 10 Guests 3 Bedrooms 3 Bathrooms
Group Friendly Bed & Breakfast
  • Pool
  • Balcony/Terrace
  • Breakfast
R2,145/Night For 7 Nights R15,016
8.4
Excellent
(14 Reviews)
4844 ft² 15 Guests 8 Bedrooms 1 Bathroom
Family Friendly Other
  • Private Pool
  • Fireplace/Heating
  • Pool
R16,271/Night For 7 Nights R113,903
New
10 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
R19,343/Night For 7 Nights R135,392
New
592 ft² 11 Guests 6 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
R14,165/Night For 7 Nights R99,149

Why Choose Rent By Owner for your Chessy Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chessy

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation here can significantly enhance your experience, so consider visiting during the region's shoulder seasons when the area offers a perfect balance of pleasant weather and fewer crowds for an enjoyable stay.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities around the area.

Average Temperature Daytime: 25-30°C - Nighttime: 15-20°C
winter
Winter (December to February)

The winter season draws visitors seeking a festive atmosphere and picturesque snowy landscapes, perfect for holiday celebrations in this destination.

Average Temperature Daytime: 0-5°C - Nighttime: -5 to 0°C

Off-Season Highlights

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Spring (March to May)

This is an excellent time for travelers looking to explore with fewer crowds, as the region begins to bloom and enjoy milder weather.

Average Temperature Daytime: 12-20°C - Nighttime: 5-10°C
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Autumn (September to November)

Visit during the fall when the scenery transforms with colorful foliage, offering a tranquil atmosphere ideal for relaxing stays.

Average Temperature Daytime: 15-22°C - Nighttime: 8-14°C

Weekly Weather Forecast for Chessy

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • You can enjoy a private outdoor space such as a patio or terrace, perfect for relaxing after exploring the region.
  • Look forward to a well-maintained garden area where you can unwind amidst lush surroundings.
  • A pool might be available, offering a refreshing way to beat the summer heat in this scenic destination.
  • Many properties feature barbecue facilities, ideal for outdoor dining during your stay here.
  • Expect outdoor dining areas that allow you to savor meals while taking in the beautiful views of the surrounding countryside.
  • If you're seeking adventure, some rentals provide access to outdoor sports amenities like tennis courts or bike paths nearby.
  • Enjoy the convenience of parking spaces located right outside, facilitating easy exploration of the region's attractions.
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Family Activities

  • Disneyland Park Paris: Experience magical moments with your family at this world-famous theme park, just a short drive from here, offering enchanting rides and entertainment for all ages.
  • La Mer de Sable: Enjoy a fun-filled day at this adventure park in the region, where you can explore themed attractions, scenic rides, and live shows perfect for young explorers.
  • Chateau de la Rochepot: Discover the historic charm of this nearby castle, providing engaging tours and picturesque grounds that make for an educational family outing.
  • Local Nature Trails and Parks: Take advantage of the area's scenic walking paths and parks, ideal for picnics and outdoor activities that allow your family to connect with nature during your stay.
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Adult Activities

  • Wine Tasting Tours: Explore the region's renowned vineyards and indulge in wine tasting experiences that showcase the area's rich vinicultural heritage.
  • Gourmet Dining Experiences: Savor exceptional local cuisine at fine restaurants, offering authentic flavors that highlight the region's culinary excellence.
  • Historical Museum Visits: Discover the area's fascinating history and cultural heritage through engaging exhibits and collections curated for visitors.
  • Guided Nature Walks: Enjoy scenic trails and guided walks in the surrounding natural landscapes, perfect for relaxing and appreciating the region's beauty.

Other Places to Stay in Chessy

Chessy Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take the opportunity to enjoy authentic regional dishes at nearby eateries to fully immerse yourself in the local flavor of this destination.
  • Plan Convenience-Focused Activities: Schedule your days around major attractions and natural landmarks to maximize your experience and make the most of your stay here.
  • Choose a Prime Location: Select vacation rentals positioned close to key transportation routes or popular spots for easy access and added convenience during your visit.
  • Connect with the Community: Engage with local events or markets to gain insight into the area's culture and enhance your overall travel experience.

Transportation Options

  • Train Services: You can conveniently access high-speed rail connections here, making it easy to explore the region and beyond from this central transit point.
  • Bus Transportation: Local bus routes provide affordable and reliable options for getting around, connecting you to nearby attractions and surrounding towns.
  • Taxi and Ride-Sharing: Taxis and ride-sharing services are readily available, offering a flexible way to travel directly from your vacation rental in the area.
  • Car Rentals: Renting a car gives you the freedom to explore the region at your own pace, with several rental agencies operating close by for your convenience.

Local Customs Options

  • Local Greetings and Manners: When visiting this destination, it’s customary to greet neighbors with a polite handshake or a friendly "Bonjour," reflecting the region's warm hospitality.
  • Traditional Food Etiquette: Dining here often involves sharing local specialties with an emphasis on communal meals, where traditional table manners are highly valued.
  • Celebration of Local Festivals: Participating in regional festivals is a key custom, showcasing the area's rich cultural heritage through music, dance, and local costumes.
  • Respect for Historical Sites: Visitors are encouraged to honor the area's historical landmarks by maintaining decorum and adhering to guidelines to preserve the region's heritage.

Frequently Asked Questions About Chessy?

2. How many vacation rentals have private pools in Chessy?

There are 4 vacation rentals with private pools near Chessy. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Chessy are best for families?

If you are looking for a family-friendly vacation home in Chessy, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chessy:

4. How many Rentbyowner vacation rentals are available in Chessy?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 99 in the Chessy area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chessy. 

5. What is the cancellation policy for a vacation rental in this region?

The cancellation policy varies depending on the property listing. You should review the specific terms on the listing page and contact the owner directly for detailed information.

6. How do I ensure my stay in a vacation rental here meets my expectations?

You can find detailed descriptions, photos, and guest reviews on each listing to help you make an informed decision. It's also recommended to communicate with the property owner regarding any special requirements.

7. Are there any fees or additional charges when booking a vacation rental in this area?

Additional fees such as cleaning fees, security deposits, or service charges may apply. These are usually detailed in the listing, but it's best to confirm with the owner before completing your reservation.

8. What amenities are typically included in vacation rentals in this region?

Most properties offer essential amenities like Wi-Fi, kitchen facilities, and parking. Specific amenities vary by property, so be sure to review the listing details for the exact features available.

9. How can I communicate with property owners during my booking process?

You can send direct messages through the booking platform to clarify details or ask questions about the vacation rental. This ensures you have all the information needed before confirming your stay.

Chessy Top Rated Vacation Rentals

9.8
Exceptional
(92 Reviews)
538.2 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation Apartment
  • Oceanfront
  • Spa
  • Fireplace/Heating
R2,892/Night For 7 Nights R20,241
9.8
Exceptional
(56 Reviews)
538.2 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View House
  • Oceanfront
  • Hot Tub
  • Spa
R2,746/Night For 7 Nights R19,222
9.6
Exceptional
(70 Reviews)
1 Bedroom 1 Bathroom
Family Friendly House
  • Private Pool
  • Spa
  • Fireplace/Heating
R3,063/Night For 7 Nights R21,440
9.3
Exceptional
(82 Reviews)
172.22 ft² 2 Guests 1 Bedroom 1 Bathroom
Free Cancellation Bed & Breakfast
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
R1,669/Night For 7 Nights R11,681
9.2
Exceptional
(64 Reviews)
645.83 ft² 4 Guests 1 Bedroom 1 Bathroom
Free Cancellation Apartment
  • Oceanfront
  • Fireplace/Heating
  • Pool
R2,261/Night For 7 Nights R15,821
8.9
Fabulous
(103 Reviews)
322.92 ft² 15 Guests 5 Bedrooms 5 Bathrooms
Family Friendly Bed & Breakfast
  • Private Pool
  • Hot Tub
  • Spa
R3,733/Night For 7 Nights R26,122
8.8
Fabulous
(188 Reviews)
688.89 ft² 9 Bathrooms
Ocean View Hotel
  • Private Pool
  • Oceanfront
  • Hot Tub
R18,778/Night For 7 Nights R131,449
8.8
Fabulous
(69 Reviews)
360.6 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation Bed & Breakfast
  • Oceanfront
  • Fireplace/Heating
  • Pool
R1,587/Night For 7 Nights R11,106