This luxury 10-acre private estate, a detached house, is situated in Rural Caledon, a mere 5-minute drive from Bolton town centre and 48 kilometres from Toronto Pearson International Airport. This expansive property accommodates eight guests across four bedrooms and two bathrooms, boasting a chef's kitchen, a sunken living room, a 69-square-metre two-level cedar deck, and ample parking, all offering total privacy with pond views.
Bolton
27/06 – 04/07
$271/nighttotal: $1897 (7 )
Guesthouse In Brampton-caledon 2br 2.5ba
1 2
apartment , Bolton
This private, spacious walkout basement guest suite is located on the Brampton-Caledon border, a 36-kilometre drive from Toronto Pearson Airport and a 2-minute walk to a local park. This self-contained apartment offers two en-suite bedroom suites accommodating up to six guests, featuring a fully equipped kitchen, dedicated workspace, 85-inch smart TV, keyless entry, free driveway parking for two cars, and access to a private backyard.
Bolton
16/07 – 14/08
$352/nighttotal: $10208 (29 )
House - Near Toronto Pearson Airport
3 3
apartment , Toronto
This three-bedroom, three-bathroom flat is situated in Brampton, a family-friendly district, offering convenient access to amenities such as a grocery store, gym, bank, and restaurants within a 500-meter walk, and is located 10 kilometres from Historic Bovaird House and 12 kilometres from Black Creek Pioneer Village. This spacious accommodation accommodates up to five guests and features air conditioning, with nearby access to Downsview Park and Heart Lake Conservation Area for outdoor pursuits and Donald M. Gordon Chinguacousy Park for entertainment.
9.7 6 reviews
Bolton
27/06 – 04/07
$286/nighttotal: $2002 (7 )
Qsc Luxury 2 Bedroom Basement Apartment
1 2
apartment , Toronto
This basement flat is conveniently located in a desirable area of Toronto, just a short distance from downtown and within walking distance of major attractions like the CN Tower and the waterfront. It has consistently received excellent ratings for location, cleanliness and overall user experience. This two-bedroom property can comfortably accommodate up to six guests. The flat is equipped with modern amenities such as air conditioning, a fully equipped kitchen, parking for two cars, and high-speed internet.
Bolton
16/07 – 14/08
$1069/nighttotal: $31001 (29 )
3+1 Bedroom 3 Bath Detached Home For Rent
1 3
apartment , Bolton
This apartment is located in a quiet district of Bolton, offering a peaceful retreat perfect for families seeking a relaxing getaway close to the town's key attractions. This property accommodates up to 8 guests and features 3 bathrooms, air conditioning, and a kitchen, with internet access provided for your convenience.
9.8 12 reviews
Bolton
16/07 – 14/08
$367/nighttotal: $10643 (29 )
Cozy Kleinburg Home Near Yyz/wonderland
1 3
house , King
This three-bedroom, two-bathroom house in Kleinburg, Ontario, is situated approximately 10 km from the McMichael Canadian Art Collection and 24 km from Toronto Pearson International Airport. The 3-bedroom property sleeps 5 guests, offers a fully equipped kitchen including a dishwasher, air conditioning, a garden, parking, and internet access; nearby attractions include Canada's Wonderland and LEGOLAND Discovery Centre.
8.6 4 reviews
Bolton
27/06 – 04/07
$568/nighttotal: $3976 (7 )
Cozy And Private Basement Apartment / Ideal For Relaxation Or Work
2 2
apartment , Toronto
This Brampton apartment, a 16km drive from Toronto and a 24km drive from Toronto Pearson International Airport, provides easy access to Canada's Wonderland and Woodbine Racetrack. The two-bedroom, one-bathroom property sleeps six guests and features a well-equipped kitchen, high-speed Wi-Fi, air conditioning, and pet-friendly accommodation.
Bolton
27/06 – 04/07
$2160/nighttotal: $15120 (7 )
Perfect Group Getaway Large House With Style
6 2
apartment , Bolton
This spacious six-bedroom, six-bathroom Caledon holiday home in Bolton offers ample room for up to 16 guests and boasts extensive front and back gardens, perfect for outdoor events, with the option of a walkout basement suite providing additional living space. Situated near the Claireville and Heart Lake Conservation Areas, this property provides convenient access to outdoor pursuits, with Landmark Cinemas Caledon, Copper Creek Golf Club, and the Zanchin Automotive Soccer Centre all within a short drive.
Bolton
16/07 – 14/08
$354/nighttotal: $10266 (29 )
5brdm Luxury Home, Wit Game Room
1 3
apartment , Toronto
This five-bedroom apartment is ideally located in a convenient area of Toronto, just a short distance from major attractions and amenities. The surrounding area offers a relaxed atmosphere, perfect for families and groups seeking a comfortable stay. The property is spacious and can accommodate up to 10 guests, making it ideal for larger families or groups of friends. The apartment is equipped with modern amenities, including a fully equipped kitchen, a games room with entertainment options for all ages, and a spacious outdoor patio for enjoying the warm weather.
8.3 3 reviews
Bolton
16/07 – 14/08
$406/nighttotal: $11774 (29 )
3300 Sqft - Modern And Comfort - 3 Bdrm Getaway - Relax - Unwind - Explore - Near Toronto Pearson Airport & Toronto Downtown
3 3
house , Toronto
This Brampton property, located approximately 10.9 kilometres from Toronto Pearson International Airport, offers convenient access to attractions such as Vaughan Mills, the Mississauga Convention Centre, York University, and Casa Loma, which are between 17.7 and 29 kilometres away. This spacious 307 square metre residence accommodates up to 11 guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, complimentary private parking, and free WiFi, making it a comfortable base for exploring the Toronto area.
9.0 25 reviews
Bolton
16/07 – 14/08
$194/nighttotal: $5626 (29 )
Tosam Luxury Lodge Two Bedroom Suite
2 3
apartment , Toronto
This two-bedroom flat is located in Brampton, a suburb just west of Toronto, 30 kilometres from Canada's Wonderland and 37 kilometres from Casa Loma. The apartment has received excellent user ratings and very good ratings for location and cleanliness. The 93 square metre flat comfortably sleeps four guests. It offers a range of amenities, including free Wi-Fi, private parking, a fully equipped kitchen, outdoor dining space, and air conditioning.
10 2 reviews
Bolton
27/06 – 04/07
$830/nighttotal: $5810 (7 )
Big House With Big Backyard Pool & Pool Table
6 2
bungalow , King
This six-bedroom property in King, Ontario, is situated approximately 32km from Canada's Wonderland, 48km from Toronto Pearson International Airport, and 64km from downtown Toronto. Sleeping up to 14 guests, this self-catering apartment boasts a private pool (seasonal), BBQ, full kitchen, family room, laundry facilities, pool table, ample parking, and is close to golf courses.
Best family friendly Bolton vacation rentals
Among the 20 accommodations in Bolton, here are the 4 best family friendly rentals
9.0 25 reviews
Bolton
16/07 – 14/08
$194/nighttotal: $5626 (29 )
Tosam Luxury Lodge Two Bedroom Suite
2 3
apartment , Toronto
This two-bedroom flat is located in Brampton, a suburb just west of Toronto, 30 kilometres from Canada's Wonderland and 37 kilometres from Casa Loma. The apartment has received excellent user ratings and very good ratings for location and cleanliness. The 93 square metre flat comfortably sleeps four guests. It offers a range of amenities, including free Wi-Fi, private parking, a fully equipped kitchen, outdoor dining space, and air conditioning.
9.8 12 reviews
Bolton
16/07 – 14/08
$367/nighttotal: $10643 (29 )
Cozy Kleinburg Home Near Yyz/wonderland
1 3
house , King
This three-bedroom, two-bathroom house in Kleinburg, Ontario, is situated approximately 10 km from the McMichael Canadian Art Collection and 24 km from Toronto Pearson International Airport. The 3-bedroom property sleeps 5 guests, offers a fully equipped kitchen including a dishwasher, air conditioning, a garden, parking, and internet access; nearby attractions include Canada's Wonderland and LEGOLAND Discovery Centre.
8.3 3 reviews
Bolton
16/07 – 14/08
$406/nighttotal: $11774 (29 )
3300 Sqft - Modern And Comfort - 3 Bdrm Getaway - Relax - Unwind - Explore - Near Toronto Pearson Airport & Toronto Downtown
3 3
house , Toronto
This Brampton property, located approximately 10.9 kilometres from Toronto Pearson International Airport, offers convenient access to attractions such as Vaughan Mills, the Mississauga Convention Centre, York University, and Casa Loma, which are between 17.7 and 29 kilometres away. This spacious 307 square metre residence accommodates up to 11 guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, complimentary private parking, and free WiFi, making it a comfortable base for exploring the Toronto area.
8.6 4 reviews
Bolton
27/06 – 04/07
$568/nighttotal: $3976 (7 )
Cozy And Private Basement Apartment / Ideal For Relaxation Or Work
2 2
apartment , Toronto
This Brampton apartment, a 16km drive from Toronto and a 24km drive from Toronto Pearson International Airport, provides easy access to Canada's Wonderland and Woodbine Racetrack. The two-bedroom, one-bathroom property sleeps six guests and features a well-equipped kitchen, high-speed Wi-Fi, air conditioning, and pet-friendly accommodation.
Best Bolton vacation rentals with parking
Bolton
27/06 – 04/07
$181/nighttotal: $1267 (7 )
The Refresh Stream
2 2
apartment , Toronto
This Brampton basement flat, a 25-30 minute drive (approx. 32-39km) from Square One Shopping Centre and 15 minutes (approx. 16km) from Bramalea City Centre, offers convenient access to Toronto Pearson International Airport (YYZ). Sleeping up to six guests, this two-bedroom, one-bathroom self-contained apartment features two fireplaces, a fully equipped kitchen including a conventional oven and toaster oven, air conditioning, parking, and internet access; nearby amenities include walking trails and Canada's Wonderland.
Bolton
27/06 – 04/07
$144/nighttotal: $1008 (7 )
Cozy Private Basement Near Toronto Airport
1 2
apartment , Toronto
This self-contained basement flat is located in Ebenezer East, Brampton, offering a peaceful retreat just 5 kilometres from Toronto Pearson International Airport and conveniently situated for access to Vaughan Mills Mall, Yorkdale Shopping Centre, Downsview Park, Rogers Centre, and Canada's Wonderland. This one-bedroom, one-bathroom flat accommodates two guests and features air conditioning, Wi-Fi, and parking, with pets welcome, making it a practical choice for travellers seeking a well-equipped base with easy access to major transport links and entertainment venues.
Bolton
27/06 – 04/07
$174/nighttotal: $1218 (7 )
Cozy And Charming Apartment With A Living Room And Bedroom In Brampton
1 2
apartment , Toronto
This Brampton apartment, conveniently located near grocery stores, medical clinics, and a library, offers easy access to Toronto attractions such as Canada's Wonderland and Vaughan Mills shopping centre, approximately 30-40km away. The one-bedroom, one-bathroom flat sleeps two guests and includes private laundry, Wi-Fi, Netflix, and a dedicated workspace; nearby amenities include a gym and plazas.
10 2 reviews
Bolton
27/06 – 04/07
$1351/nighttotal: $9457 (7 )
Fields & Sunsets
5 2
apartment , Caledon East
This five-bedroom Caledon East property is situated 5km from Downey's Farm Market and within a 10-16km radius of the Brampton Fair Grounds, Royal Ambassador Banquet Hall, and Albion-Bolton Fairgrounds. The self-catering house sleeps ten guests, boasting four bathrooms, a fully equipped kitchen including a dishwasher, a patio, and a Smart TV; in-unit laundry facilities are also provided.
Frequently Asked Questions about vacation rentals in Bolton
Which neighborhood in Bolton should you consider for a vacation rental?
For a central location, Bolton Town Square is ideal. You'll be close to shops, restaurants, and the Bolton Museum. If you prefer a quieter setting, Glen Williams offers a more rural feel with beautiful scenery.
What are the best Airbnb and vacation rentals in Bolton?
What are the top family-friendly attractions in Bolton?
The Bolton Fairgrounds hosts many events throughout the year, including the popular Bolton Fall Fair. For a fun day out, the Caledon Animal Shelter is a great place to visit and interact with animals. The Caledon Trailway offers scenic cycling and walking trails, perfect for a family outing.
When is the best time to book a vacation rental in Bolton?
The best time to book is in the spring or autumn when the weather is pleasant and there are fewer crowds. The Bolton Fall Fair is a popular event in September, so if you want to attend, book well in advance.
What are the best vacation rentals with a pool in Bolton?
What events or festivals should visitors check out in and around Bolton?
The Bolton Fall Fair is a must-see, with live music, food stalls, and agricultural displays. For something different, the Caledon Hills Arts Festival in June showcases local artists and musicians.
What are the best rentals for families and kids in Bolton?
What are the best budget-friendly activities in Bolton?
A stroll through Bolton Town Square is free and offers a glimpse of local life. The Caledon Trailway is perfect for a budget-friendly walk or cycle, and you can pack a picnic lunch to enjoy along the way.
What are the best rentals or Airbnbs with a jacuzzi in Bolton?
What are the best restaurants with local dishes in Bolton?
The Bolton Grill is a local favourite, known for its burgers and fries. For a more upscale dining experience, The Millcroft Inn offers a sophisticated menu with fresh, seasonal ingredients.
What are the best walking or cycling routes in Bolton?
The Caledon Trailway is a popular choice, offering over 40km of paved trails. For a shorter walk, the Bolton Town Square loop is a pleasant route with plenty of shops and cafes to stop at along the way.
Are there pet-friendly attractions in Bolton?
The Caledon Trailway is a great option for a walk or cycle with your furry friend. Many of the cafes and restaurants in Bolton Town Square also have outdoor seating where you can enjoy a meal with your dog.
What are the benefits of choosing a vacation rental in Bolton?
Vacation rentals offer more space and privacy than a hotel room. They can also be a more affordable option, especially for families or groups. You'll often find that they have a more homey feel, making you feel more at ease.
What are the top sports attractions and facilities in Bolton?
Bolton is home to the Caledon Community Complex, which offers a variety of sports facilities, including an indoor pool, ice rink, and fitness centre. The Bolton Golf Club is another great option for those who enjoy the sport.
Destinations nearby
Best Bolton vacation rentals with a balcony
Bolton
27/06 – 04/07
$2160/nighttotal: $15120 (7 )
Perfect Group Getaway Large House With Style
6 2
apartment , Bolton
This spacious six-bedroom, six-bathroom Caledon holiday home in Bolton offers ample room for up to 16 guests and boasts extensive front and back gardens, perfect for outdoor events, with the option of a walkout basement suite providing additional living space. Situated near the Claireville and Heart Lake Conservation Areas, this property provides convenient access to outdoor pursuits, with Landmark Cinemas Caledon, Copper Creek Golf Club, and the Zanchin Automotive Soccer Centre all within a short drive.
Bolton
27/06 – 04/07
$174/nighttotal: $1218 (7 )
Cozy And Charming Apartment With A Living Room And Bedroom In Brampton
1 2
apartment , Toronto
This Brampton apartment, conveniently located near grocery stores, medical clinics, and a library, offers easy access to Toronto attractions such as Canada's Wonderland and Vaughan Mills shopping centre, approximately 30-40km away. The one-bedroom, one-bathroom flat sleeps two guests and includes private laundry, Wi-Fi, Netflix, and a dedicated workspace; nearby amenities include a gym and plazas.
Best pet friendly Bolton vacation rentals
Among the 20 accommodations in Bolton, here are the 3 best pet friendly rentals
Bolton
16/07 – 14/08
$337/nighttotal: $9773 (29 )
Four Bedroom House Walking Distance From Downtown
1 3
apartment , Bolton
This four-bedroom house in Bolton is located in a quiet neighbourhood, a short walk from the town's shops and restaurants, and directly beside a park with a walking trail. This fully furnished property accommodates up to eight guests with two king and two queen beds, featuring a well-equipped kitchen with coffee pods, a smart TV, and dedicated driveway parking for one large or two smaller vehicles.
Bolton
27/06 – 04/07
$1520/nighttotal: $10640 (7 )
Whispering Ridge Retreat
1 2
apartment , Bolton
This five-bedroom, three-bathroom house in Bolton, precise location unspecified, offers comfortable accommodation for up to ten guests. The property includes a kitchen, air conditioning, parking, and internet access; further details on amenities and proximity to Bolton attractions, such as the Bolton Museum and Art Gallery, are needed.
Bolton
27/06 – 04/07
$495/nighttotal: $3465 (7 )
Best Neighborhood In King City And Vaughan
1 2
apartment , Nobleton
This four-bedroom, three-bathroom flat for up to ten guests offers a peaceful retreat in a quiet area of Nobleton, just a short distance from the town centre and local attractions. This well-equipped apartment features air conditioning, a garden, and a kitchen complete with a fridge, freezer, microwave, and dishwasher, with pets welcome and internet provided.