Cherry Valley holiday homes

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:25 Dec - 1 Jan

Living Room
Waterfront cottage
Dining Area
Professional Pool Table
Wonderful
(19 reviews)

West Lake Waterfront - YomanChic Cottage

Prince Edward

8% off
NZ$5,243
for 7 nights, 1 cottage
NZ$749 per night
includes taxes & fees
West Lake Waterfront - YomanChic Cottage
Outdoor spa tub
Property grounds
Private kitchen
Interior
Exceptional
(66 reviews)

Nordic Hideaway at Wellington on the Beach

Prince Edward

8% off
NZ$2,425
for 7 nights, 1 home
NZ$346 per night
includes taxes & fees
Nordic Hideaway at Wellington on the Beach
Dining
Terrace/patio
Private kitchen
Exterior
Exceptional
(34 reviews)

Cozy urban cottage in the heart of Picton

Prince Edward

8% off
NZ$2,385
for 7 nights, 1 home
NZ$341 per night
includes taxes & fees
Cozy urban cottage in the heart of Picton
Living area
Outdoor dining
Room
Living area
Exceptional
(6 reviews)

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

Prince Edward

6% off
NZ$3,154
for 7 nights, 1 home
NZ$451 per night
includes taxes & fees
Charming Picton Bungalow! Dog friendly! Walk to the Millenium Trail and Main St!
Private kitchen
Room
Private kitchen
Exterior
Wonderful
(14 reviews)

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

Prince Edward

7% off
NZ$2,973
for 7 nights, 1 apartment
NZ$425 per night
includes taxes & fees
Large 2BR, new beautiful modern fully renovated apt just off Main St. Picton
Interior
Outdoor spa tub
Dining
Interior
Excellent
(17 reviews)

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

Prince Edward

15% off
NZ$1,938
for 7 nights, 1 home
NZ$277 per night
includes taxes & fees
Spacious Century 3-bed in Downtown Wellington with in Ground Pool and parking!
View of the living room from the kitchen
The entrance to the beach from the Sandbanks Cafe
View of the kitchen from the living room
Your deck from the kitchen w/access to the backyard.
Exceptional
(50 reviews)

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

Prince Edward

9% off
NZ$1,589
for 7 nights, 1 apartment
NZ$227 per night
includes taxes & fees
Peaceful, quiet & spacious retreat right in the heart of quaint downtown Picton!
  • Peace of mind

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  • 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 Cherry Valley

  • Stunning nature reserves: Discover the breathtaking landscapes and serene environments perfect for outdoor adventures in Cherry Valley.
  • Cherry Blossom Festival: Experience the vibrant spring festival celebrating beautiful cherry trees and local culture.
  • Local wineries: Explore nearby wineries and indulge in the region's finest wines for a true taste of Ontario.
  • Historic lighthouse: Visit the iconic lighthouse that adds charm and history to the picturesque setting of Cherry Valley.
  • Family-friendly atmosphere: Enjoy the welcoming community vibe that's perfect for a relaxing getaway with loved ones.

Top attractions near Cherry Valley

Cherry Valley, Ontario, offers a delightful mix of beach relaxation, wellness, and cultural experiences. Visitors can explore the stunning nature reserves, local galleries, and the historic lighthouse, all while enjoying outdoor adventures. Don’t miss the vibrant Cherry Blossom Festival in spring, where you can admire the beautiful cherry trees and discover nearby local wineries for a taste of the region's finest wines. Perfect for a getaway that combines relaxation with exploration.

  • Lake on the Mountain Provincial Park: A stunning natural reserve located 14.5km from Cherry Valley, offering serene landscapes and tranquil vibes. It's perfect for a relaxing day out, with scenic views that inspire peace and reflection.
  • Bloomfield Studios and Gallery: Situated 8.0km away, this vibrant gallery showcases local culture through diverse artworks. Immerse yourself in the creative atmosphere and appreciate the talent of regional artists.
  • County Youth Park: Just 8.0km from Cherry Valley, this urban park is ideal for families. With outdoor spaces for play and relaxation, it offers a lively environment perfect for enjoying the city vibes.

Things to do recommended for couples

For a romantic getaway in Cherry Valley, explore Caddy Shack Mini Golf for some fun-filled competition. Then, indulge in the charm of Waupoos and Huff Estates Wineries, both offering delightful experiences just a short drive away, perfect for a couple’s retreat.

Things to do recommended for families

Families visiting Cherry Valley can enjoy the stunning Sandbanks Provincial Park, located 11.3km away. This recreational area is perfect for relaxation and fun, offering beautiful beaches and opportunities for swimming, picnicking, and exploring nature trails, ensuring a memorable experience for everyone.

Things to do recommended for groups

Enjoy a round of golf at Wellington on the Lake Golf Course, experience the charm of Casa-Dea Estates Winery for some delightful tastings, or unleash your competitive spirit at PRZ Paintball for an adventure-packed day, all within a short drive from Cherry Valley.

*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 in Cherry Valley

If you're heading off with a group, family, or pets, or if you're considering an extended stay, be sure to apply the right filters to meet your needs. Here are some handy Vrbo booking tips to assist you.

  • Traveling to Cherry Valley with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Cherry Valley with young kids: Traveling with little ones can be a bit 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 Cherry Valley: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your whole family feels comfortable and at ease.
  • Planning for a long term stay visiting Cherry Valley: 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. With the right filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Cherry Valley

Cherry Valley, nestled in Prince Edward, Ontario, offers a delightful blend of beach relaxation and family-friendly vibes. Explore the enchanting Cherry Blossom destination, stroll through the picturesque Blossom Valley, and immerse yourself in the local culture at the Cherry Valley Festival. With its friendly people and tranquil atmosphere, this charming village is perfect for a rejuvenating getaway, where you can enjoy the beauty of cherry trees and the warmth of the community.

  • Prince Edward: Prince Edward is a vibrant city that encompasses Cherry Valley, offering a mix of business, family, and urban experiences. Nestled in the heart of Ontario's beautiful countryside, this area is perfect for those looking to unwind amidst nature while still enjoying city conveniences. Popular activities include visits to local recreational areas and shopping centres. You can explore stunning local landmarks like the picturesque beaches and serene lakes, as well as the lush nature reserves that provide ample opportunities for hiking and wildlife spotting.
  • Picton: Located a mere 8.0km from Cherry Valley, Picton is a charming village that welcomes visitors with its delightful atmosphere. Known for its family-friendly vibe and business-friendly amenities, Picton offers a range of activities including shopping at local stores and enjoying recreational areas. The village is surrounded by natural beauty, with nearby beaches and lakes ideal for relaxing or engaging in outdoor adventures. Don't miss the chance to visit the local nature reserves, which are perfect for a day of exploration and connecting with the region's diverse ecosystems.
  • Milford: Milford is a quaint village located 4.8km from Cherry Valley, providing a peaceful retreat for travellers. Like its neighbours, Milford is known for its welcoming atmosphere and a blend of business and family experiences. The village features recreational areas and shopping outlets, making it easy to enjoy a leisurely day. With proximity to beautiful beaches, tranquil lakes, and lush nature reserves, Milford offers numerous outdoor activities, ensuring that visitors can immerse themselves in the stunning natural landscape that defines this part of Ontario.

Best time to go to Cherry Valley

If you're planning a trip to Cherry Valley, it's a good idea to check both the weather and property rates. The warmest month is July.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.6°F (-5.8°C)Light RainMostly Cloudy
February22.5°F (-5.3°C)Light RainMostly Cloudy
March31.5°F (-0.3°C)Light RainMostly Cloudy
April42.6°F (5.9°C)Light RainMostly Cloudy
May55.6°F (13.1°C)Light RainMostly Sunny
June64.0°F (17.8°C)Light RainMostly Sunny
July70.5°F (21.4°C)Light RainMostly Sunny
August69.4°F (20.8°C)Light RainMostly Sunny
September62.8°F (17.1°C)Light RainMostly Sunny
October51.1°F (10.6°C)Light RainMostly Sunny
November39.0°F (3.9°C)Light RainMostly Sunny
December29.7°F (-1.3°C)Light RainMostly Cloudy

Booking with Vrbo is a breeze

Planning your next adventure and want to save some dosh? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, if you book a longer stay, you could enjoy some substantial savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new holidays, manage your existing arrangements, or keep track of your bookings. The properties you’ve saved or reserved are neatly categorised into Potential, Upcoming, or Current Trips. To check out your Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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)
  • Bay of Quinte (15 mi / 24.2 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 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 Cherry Valley holiday homes with parking?
Bookabach 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 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 Cherry Valley holiday home booking on Bookabach?
To find Cherry Valley 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 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 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 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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Cherry Valley 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.

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