Discover Your Perfect Chessy Vacation Homes

Best Vacation Homes in Chessy

House
Map-icon
like-icon10.0
Exceptional
(9 Reviews)
1 Bedroom 1 Bath 6 Guests 753 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $142/Night 7 Nights - US $992
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House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 6 Guests 807.29 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $109/Night 7 Nights - US $761
Bed & Breakfast
Map-icon
like-icon9.8
Exceptional
(108 Reviews)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $124/Night 7 Nights - US $868
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 2 Guests 474 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $134/Night 7 Nights - US $936
star-icons-3
Apartment
like-icon9.8
Exceptional
(4 Reviews)
1 Bedroom 1 Bath 4 Guests 645.83 ft²
  • Parking
    Parking
  • Internet
    Internet
More amenities
US $64/Night 7 Nights - US $446
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 3 Guests 484 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $83/Night 7 Nights - US $581
Apartment
Map-icon
like-icon9.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests 431 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $98/Night 7 Nights - US $689
House
Map-icon
like-icon8.0
Excellent
(1 Review)
1 Bedroom 1 Bath 2 Guests 215 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $59/Night 7 Nights - US $414

Chessy Luxury Rentals

House
Map-icon
11 Bedrooms 7 Baths 34 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $1,665/Night 7 Nights - US $11,657
House
like-icon10.0
Exceptional
(1 Review)
10 Bedrooms 9 Baths 29 Guests 4951 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $1,650/Night 7 Nights - US $11,550
House
Map-icon
5 Bedrooms 2 Baths 13 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
US $1,263/Night 7 Nights - US $8,840
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Villa
Map-icon
like-icon9.5
Exceptional
(2 Reviews)
5 Bedrooms 4 Baths 14 Guests 5381.95 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $1,237/Night 7 Nights - US $8,659
Cottage
like-icon10.0
Exceptional
(2 Reviews)
8 Bedrooms 8 Baths 30 Guests 5920 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $1,184/Night 7 Nights - US $8,289
House
Map-icon
6 Bedrooms 6 Baths 15 Guests 3122 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $1,160/Night 7 Nights - US $8,117
Other
Map-icon
like-icon8.4
Excellent
(14 Reviews)
8 Bedrooms 1 Bath 15 Guests 4844 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $1,018/Night 7 Nights - US $7,123
House
Map-icon
4 Bedrooms 2 Baths 8 Guests 2153 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $758/Night 7 Nights - US $5,309

Chessy Pet Friendly Vacation Rentals

House
Map-icon
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $142/Night 7 Nights - US $994
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Bed & Breakfast
Map-icon
like-icon9.7
Exceptional
(6 Reviews)
2 Bedrooms 2 Baths 4 Guests 134.55 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
US $80/Night 7 Nights - US $563
House
Map-icon
like-icon10.0
Exceptional
(9 Reviews)
5 Bedrooms 3 Baths 12 Guests 1830 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $581/Night 7 Nights - US $4,066
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Bed & Breakfast
Map-icon
like-icon9.6
Exceptional
(122 Reviews)
2 Bedrooms 2 Baths 8 Guests 258.33 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $96/Night 7 Nights - US $672
House
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 7 Guests 980 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
US $121/Night 7 Nights - US $845
House
like-icon9.8
Exceptional
(6 Reviews)
4 Bedrooms 2 Baths 11 Guests 1851 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
US $289/Night 7 Nights - US $2,026
House
Map-icon
like-icon8.0
Excellent
(1 Review)
4 Bedrooms 2 Baths 8 Guests 2476 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $546/Night 7 Nights - US $3,823
House
Map-icon
4 Bedrooms 3 Baths 8 Guests 1507 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $277/Night 7 Nights - US $1,938

Chessy Large Vacation Homes

House
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 13 Guests 1507 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
US $233/Night 7 Nights - US $1,631
star-icons-3
House
Map-icon
like-icon9.3
Exceptional
(209 Reviews)
5 Bedrooms 2 Baths 7 Guests 344.44 ft²
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
US $128/Night 7 Nights - US $894
House
like-icon10.0
Exceptional
(1 Review)
10 Bedrooms 9 Baths 29 Guests 4951 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $1,812/Night 7 Nights - US $12,682
Villa
Map-icon
like-icon8.0
Excellent
(1 Review)
4 Bedrooms 2 Baths 8 Guests 2583 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
US $583/Night 7 Nights - US $4,079
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.3
Exceptional
(5 Reviews)
3 Bedrooms 3 Baths 10 Guests 269.1 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $131/Night 7 Nights - US $914
House
Map-icon
5 Bedrooms 5 Baths 14 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
US $1,222/Night 7 Nights - US $8,556
House
4 Bedrooms 2 Baths 10 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $1,177/Night 7 Nights - US $8,241
House
Map-icon
6 Bedrooms 3 Baths 11 Guests 592 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $862/Night 7 Nights - US $6,035

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 5 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 98 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

star-icons-4
Apartment
like-icon9.8
Exceptional
(92 Reviews)
2 Bedrooms 2 Baths 4 Guests 538.2 ft²
  • Oceanfront
    Oceanfront
  • Spa
    Spa
More amenities
US $176/Night 7 Nights - US $1,232
star-icons-3
House
Map-icon
like-icon9.7
Exceptional
(64 Reviews)
1 Bedroom 1 Bath 2 Guests 538.2 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
US $167/Night 7 Nights - US $1,170
House
Map-icon
like-icon9.6
Exceptional
(72 Reviews)
1 Bedroom 1 Bath
  • Private Pool
    Private Pool
  • Spa
    Spa
More amenities
US $187/Night 7 Nights - US $1,310
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.6
Exceptional
(21 Reviews)
2 Bedrooms 1 Bath 2 Guests 161.46 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $124/Night 7 Nights - US $871
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.3
Exceptional
(82 Reviews)
1 Bedroom 1 Bath 2 Guests 172.22 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $102/Night 7 Nights - US $711
star-icons-3
Apartment
Map-icon
like-icon9.2
Exceptional
(64 Reviews)
1 Bedroom 1 Bath 4 Guests 645.83 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $138/Night 7 Nights - US $963
star-icons-4
Bed & Breakfast
Map-icon
like-icon9.0
Exceptional
(87 Reviews)
5 Bedrooms 5 Baths 15 Guests 322.92 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
US $251/Night 7 Nights - US $1,755
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Bed & Breakfast
Map-icon
like-icon8.8
Fabulous
(68 Reviews)
2 Bedrooms 2 Baths 4 Guests 360.6 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $97/Night 7 Nights - US $676