Cherry Valley holiday rentals

We found 385 holiday rentals — enter your dates for availability
Select from 82 homes, 13 cottages and other holiday rentals in Cherry Valley to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Cherry Valley

Showing deals for:18 Dec - 25 Dec

Dining Area
Waterfront cottage
Living Room
Master bedroom - King bed
Wonderful
(19 reviews)

West Lake Waterfront - YomanChic Cottage

Prince Edward

8% off
AU$4,126
for 7 nights, 1 cottage
AU$589 per night
includes taxes & fees
West Lake Waterfront - YomanChic Cottage
Interior
Property grounds
Outdoor spa tub
Interior
Exceptional
(66 reviews)

Nordic Hideaway at Wellington on the Beach

Prince Edward

8% off
AU$1,992
for 7 nights, 1 home
AU$285 per night
includes taxes & fees
Nordic Hideaway at Wellington on the Beach
Dining
Terrace/patio
Interior
Private kitchen
Exceptional
(33 reviews)

Cozy urban cottage in the heart of Picton

Prince Edward

7% off
AU$1,959
for 7 nights, 1 home
AU$280 per night
includes taxes & fees
Cozy urban cottage in the heart of Picton
Living area
Outdoor dining
Living area
Room
Exceptional
(6 reviews)

Charming Picton Bungalow! Dog friendly! Walk to the Millenium Trail and Main St!

Prince Edward

6% off
AU$2,553
for 7 nights, 1 home
AU$365 per night
includes taxes & fees
Charming Picton Bungalow! Dog friendly! Walk to the Millenium Trail and Main St!
Exterior
Room
Private kitchen
Private kitchen
Wonderful
(14 reviews)

Large 2BR, new beautiful modern fully renovated apt just off Main St. Picton

Prince Edward

7% off
AU$2,488
for 7 nights, 1 apartment
AU$355 per night
includes taxes & fees
Large 2BR, new beautiful modern fully renovated apt just off Main St. Picton
Pool
Outdoor spa tub
Interior
Interior
Excellent
(17 reviews)

Spacious Century 3-bed in Downtown Wellington with in Ground Pool and parking!

Prince Edward

15% off
AU$1,555
for 7 nights, 1 home
AU$222 per night
includes taxes & fees
Spacious Century 3-bed in Downtown Wellington with in Ground Pool and parking!
Exterior detail
The entrance to the beach from the Sandbanks Cafe
Your deck from the kitchen w/access to the backyard.
View of the living room from the kitchen
Exceptional
(50 reviews)

Peaceful, quiet & spacious retreat right in the heart of quaint downtown Picton!

Prince Edward

9% off
AU$1,214
for 7 nights, 1 apartment
AU$173 per night
includes taxes & fees
Peaceful, quiet & spacious retreat right in the heart of quaint downtown Picton!

  • 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

Travel to friendly Cherry Valley

The island views and other outdoor surroundings create an inviting atmosphere in Cherry Valley. This walkable city has many special qualities. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Cherry Valley

Are you looking for attractions to visit in the city? Venture out of your holiday home and experience everything that Cherry Valley has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Picton Golf and Country Club (6.6 mi / 10.6 km)
  • Huff Estates Winery (8.7 mi / 14 km)
  • Waupoos Winery (10.6 mi / 17 km)
  • Wellington on the Lake Golf Course (10.8 mi / 17.5 km)
  • Karlo Estates Winery (11.1 mi / 17.8 km)
  • County Cider Company (11.1 mi / 17.9 km)

Exploring the natural landscape of Cherry Valley

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Cherry Valley is a great spot to appreciate mother nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Sandbanks Provincial Park (6.2 mi / 9.9 km)
  • Prince Edward County Skateboard Park (5.5 mi / 8.8 km)
  • Lake on the Mountain Provincial Park (8.7 mi / 14 km)
  • Wellington Rotary Beach (9.3 mi / 15 km)
  • Wellington Main Street Park (9.7 mi / 15.6 km)
  • Prince Edward Point National Wildlife Area (13.4 mi / 21.6 km)

Frequently asked questions

What is the best area to stay in Cherry Valley when booking a holiday rental?
When considering a holiday rental in Cherry Valley, Ontario, the area around the village itself is an excellent choice. This quaint community is known for its charm and proximity to stunning natural landscapes. You'll find a variety of properties available, ranging from cosy cottages to more spacious homes, making it suitable for different group sizes and preferences.One of the top attractions nearby is the Sandbanks Provincial Park, renowned for its beautiful sandy beaches and expansive dunes, offering a great spot for sunbathing, swimming, or picnicking. Additionally, the picturesque scenery of the surrounding countryside makes it a fantastic destination for outdoor activities such as hiking and cycling.In Cherry Valley, visitors can also enjoy local art galleries and charming shops, which provide a glimpse into the area's creative spirit. The community hosts various events throughout the year, showcasing local culture and food, ensuring a vibrant setting during your stay.
What are the top attractions in Cherry Valley?
In Cherry Valley, Ontario, visitors can enjoy a variety of attractions that showcase the natural beauty and charm of the region. The nearby Sandbanks Provincial Park is a major highlight, renowned for its stunning sandy beaches and expansive dunes, great for swimming, sunbathing, and hiking. The park offers scenic views of Lake Ontario and is an ideal spot for outdoor activities.The quaint village itself features local shops and artisanal boutiques, providing visitors with a taste of the area's craftsmanship and produce. Exploring the nearby wineries in Prince Edward County is a delightful experience, where guests can sample local wines and enjoy picturesque vineyard landscapes.For those interested in history, the nearby Black River Cheese Company offers tours and tastings, allowing visitors to learn about the cheese-making process while indulging in delicious local products.
Are all fees included in the Cherry Valley holiday homes prices shown on Stayz?
Stayz 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 Cherry Valley holiday homes with parking?
Stayz offers a wide selection of holiday homes in Cherry Valley 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 Cherry Valley holiday homes?
You can find great discounts on holiday homes in Cherry Valley on Stayz, 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 Cherry Valley holiday home booking on Stayz?
To find Cherry Valley holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Cherry Valley?
A long-stay holiday home in Cherry Valley 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 Stayz?
Stayz'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 Cherry Valley holiday home?
Book your Cherry Valley 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cherry Valley?
Prices for holiday homes in Cherry Valley 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. Stayz offers something for every taste and budget, from affordable homes in Cherry Valley to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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