This six-bedroom Bolton bungalow, perfect for large groups, offers convenient access to local amenities and Bolton's attractions, though precise distances aren't specified. Sleeping up to 16 guests, the property boasts three bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, a garden, parking and WiFi.
9.7 59 reviews
Bolton
01/09 – 30/09
$194/nighttotal: $5626 (29 )
Simple Plain Comfort
1 2
house , Bolton
This Bolton house, sleeping six, is ideally located for exploring the town centre, with its proximity to Bolton's attractions needing further clarification to determine precise distances in kilometres. The three-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, garden, parking, and is tastefully furnished for a comfortable stay, offering exclusive access for families or small groups.
This luxury flat is located in a prime district of King, offering convenient access to major landmarks and attractions. This spacious dwelling is ideal for events and creative projects, featuring an elegant stone fireplace, a full bar, and customizable lighting themes for up to 16 guests, with high-end finishes and a flexible layout that facilitates seamless setup.
Bolton
21/06 – 24/06
$1039/nighttotal: $3117 (3 )
Luxury Estate Pool Bbq Near Airport 4-bdrm
1 2
apartment , Toronto
This luxurious Castlemore estate, located in the Vales of Castlemore North, Brampton, is situated 20 kilometres from Toronto Pearson International Airport and 36 kilometres from Downtown Toronto, offering convenient access to major motorways and retail centres. This expansive property accommodates up to 12 guests, featuring a chef-ready kitchen, spa-inspired bathrooms, a private garden with a seasonal pool, and is ideal for families or executive stays with amenities including air conditioning and Wi-Fi.
9.4 32 reviews
Bolton
22/06 – 29/06
$177/nighttotal: $1239 (7 )
Cozy 1bdr Apt In Palgrave
1 2
apartment , Caledon East
This cosy one-bedroom flat is situated in Palgrave, just 10 kilometres north of Bolton/Caledon, and is located across from Caledon Hills Brewing Company. It's also just a short distance from the Trans Canada Trail and Bruce Trail, offering easy access to nature. The apartment has received excellent ratings for location, cleanliness and user experience. The flat offers one bedroom and one bathroom, accommodating up to two guests. It comes equipped with a fridge, freezer, microwave oven, dishwasher, air conditioning, internet and parking, making it a comfortable and convenient stay.
8.4 45 reviews
Bolton
20/06 – 27/06
$263/nighttotal: $1841 (7 )
Newly Built Luxurious 3brm Town Hs/airport/parking
3 2
house , Bolton
This spacious three-bedroom house in Brampton, conveniently located 11km from Toronto Pearson International Airport, offers easy access to York University (18km) and the Aviva Centre (16km). The 186 square metre property boasts a fully equipped kitchen, private parking, a garden and terrace, and sleeps up to six guests comfortably, making it ideal for families or groups visiting the area.
9.1 15 reviews
Bolton
21/06 – 24/06
$567/nighttotal: $1701 (3 )
Modern Rustic Stay Near City~entertainment Escape
1 2
apartment , Bolton
This spacious 4-bedroom detached house offers a luxurious 1-acre retreat in a nature-filled setting in Caledon, located approximately 6 kilometers from the centre of Bolton. This property boasts 4 bathrooms, accommodates up to 8 guests, and features a year-round hot tub, indoor entertainment options including a home theatre, pool table, and air hockey, a large deck for outdoor enjoyment, and a fully equipped modern kitchen, with ample parking for up to 6 cars.
9.3 122 reviews
Bolton
01/09 – 30/09
$137/nighttotal: $3973 (29 )
Chic & Cozy Basement Suite
1 2
apartment , Toronto
This Toronto basement flat, situated in a quiet neighbourhood approximately 24km from Pearson International Airport, 40km from the CN Tower, and 30km from Canada's Wonderland, offers convenient access to major attractions. The self-contained two-bedroom dwelling sleeps four guests, features a fully equipped kitchen with laundry facilities, a private entrance, and a four-piece bathroom; nearby amenities include restaurants and shopping centres.
Bolton
20/06 – 27/06
$409/nighttotal: $2863 (7 )
* Private Suite W Full Kitchen *
1 2
apartment , Toronto
This self-contained basement apartment in Toronto offers a private entrance via the garage, its precise location within the city currently unspecified, meaning proximity to downtown Toronto and specific landmarks remains undetermined. The 1-bedroom, 1-bathroom suite sleeps 4, features a full kitchen, 55" Smart TV, in-suite laundry (available after 7 pm on weekdays), and a queen-sized bed, providing comfortable self-catering accommodation for short or long stays.
Bolton
01/09 – 30/09
$200/nighttotal: $5800 (29 )
Chic & Cozy 2-bedroom Townhouse With All Amenities
2 2
apartment , Toronto
This stylish, fully furnished two-bedroom apartment is located in Brampton, offering convenient access to attractions such as Canada's Wonderland and shopping centres like Vaughan Mills Mall, approximately 18 kilometres from central Toronto. This accommodation accommodates up to four guests and features air conditioning, Wi-Fi, and allows pets, with a check-out time of 11:00 AM.
10 4 reviews
Bolton
21/06 – 24/06
$142/nighttotal: $426 (3 )
Garden-level 1-bdrm Suite With Private Entrance
1 2
house , King
This garden-level suite is located in Kleinburg, Ontario, a village known for its scenic trails and boutique shops, offering a peaceful residential setting. This brand-new, self-contained apartment accommodates two guests and features air conditioning, internet, and parking, providing a modern retreat close to Kleinburg's refined dining establishments.
Bolton
01/09 – 30/09
$199/nighttotal: $5771 (29 )
Modern 2 Bedroom Private Suite, Prime Location
2 2
apartment , Caledon East
This modern 2-bedroom flat in Caledon East is situated 17.7 kilometres from the Mississauga Convention Centre and 19.3 kilometres from Toronto Pearson International Airport, with Canada's Wonderland and Vaughan Mills Shopping Centre both 30.6 kilometres away. This 139 square metre suite accommodates up to five guests and features a fully equipped kitchen, air conditioning, complimentary private parking, and free WiFi, with check-out between 8:00 AM and 11:00 AM.
Best family friendly Bolton vacation rentals
Among the 20 accommodations in Bolton, here are the 4 best family friendly rentals
8.3 3 reviews
Bolton
01/09 – 30/09
$433/nighttotal: $12557 (29 )
3300 Sqft - Modern And Comfort - 3 Bdrm Getaway - Relax - Unwind - Explore - Near Toronto Pearson Airport & Toronto Downtown
3 2
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.
10 3 reviews
Bolton
21/06 – 24/06
$404/nighttotal: $1212 (3 )
Modern 3br Group Suite 2 Kitchens Near Airport
3 2
apartment , Toronto
This three-bedroom, two-bathroom lower suite in Brampton, Ontario, offers convenient access to major highways (Highway 427, 407, and 410), situated approximately 24km from Pearson International Airport and under 10 minutes from local amenities. The self-catering property sleeps six comfortably, boasting two fully equipped kitchens, two living areas with 65" smart TVs, premium queen beds, and kid-friendly amenities available on request; on-site driveway parking is also available.
9.0 25 reviews
Bolton
01/09 – 30/09
$194/nighttotal: $5626 (29 )
Tosam Luxury Lodge Two Bedroom Suite
2 2
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.
9.1 41 reviews
Bolton
01/09 – 30/09
$428/nighttotal: $12412 (29 )
Avid Vacation Palace In Castlemore , Brampton
3 2
house , Toronto
This holiday home is located in Castlemore, Brampton, just 19 kilometres from Aviva Centre and 21 kilometres from York University, offering easy access to both Toronto attractions and the suburbs. The property has received excellent ratings for cleanliness, location, and overall user experience. This three-bedroom property offers 1000 square metres of space and can accommodate up to six guests. The home includes a fully equipped kitchen with a dishwasher and oven, a private garden, and a comfortable living area with a flat-screen TV, air conditioning, and a fireplace.
Best Bolton vacation rentals with parking
8.6 4 reviews
Bolton
21/06 – 24/06
$610/nighttotal: $1830 (3 )
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.
10 10 reviews
Bolton
01/09 – 30/09
$276/nighttotal: $8004 (29 )
Luxurious Family Retreat Near Canada's Wonderland
1 2
apartment , Toronto
This three-bedroom house in Brampton offers convenient access to Toronto Pearson International Airport (a 15-minute drive), Canada's Wonderland (14 km), and Wet'n'Wild (8 km). The 1700 sq ft property features a fully equipped kitchen, two bathrooms, and can comfortably accommodate six guests, with amenities including a 55-inch HD TV and private parking for two cars.
9.7 5 reviews
Bolton
20/06 – 27/06
$247/nighttotal: $1729 (7 )
House ∙ 1 Bedroom ∙ 2 Guests
1 2
house , King
This off-grid cabin, situated approximately 64km north of Toronto Pearson International Airport in a rural area near King, Ontario, boasts a private bass pond and tranquil views. The self-catering cottage sleeps two, features a double bed, wood-burning fireplace, outdoor barbecue, composting toilet, and provides all linens (guests need to bring towels); nearby activities include exploring the surrounding countryside.
10 3 reviews
Bolton
01/09 – 30/09
$455/nighttotal: $13195 (29 )
Luxury Retreat With Workspace & Spacious Backyard
4 2
apartment , Bolton
This luxurious five-bedroom apartment, located in Toronto Gore Rural Estate, Brampton, is approximately 20.1 km from Toronto Pearson Airport and offers easy access to major highways and attractions such as Woodbine Racetrack and Canada's Wonderland. The 334-square-metre property boasts multiple living areas, a fully equipped kitchen with dishwasher, six bathrooms, a private garden, parking for three cars, high-speed internet (up to 1TB), and accommodates up to 16 guests.
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.
This family-friendly apartment in Brampton, Toronto, offers a riverside location with convenient access to the Heart Lake Conservation Area, just a 5-minute drive away, and Trinity Commons Shopping Centre, a 10-minute drive from the property. This spacious 358 square meter holiday home features 6 bedrooms, 5.5 bathrooms, a full kitchen with a dishwasher and oven, air conditioning, free Wi-Fi, and a private garden with a terrace, accommodating up to 22 guests.
9.0 9 reviews
Bolton
01/09 – 30/09
$621/nighttotal: $18009 (29 )
Fifa 2026 Kleinburg Luxe Town Residence 9 Queen Beds Sleeps 18
1 2
house , King
This Kleinburg Luxe Crown Town Residence is situated in Vaughan, Ontario, approximately 11 kilometres from Toronto Pearson International Airport, 11 kilometres from Canada's Wonderland, and 13 kilometres from Vaughan Mills Shopping Centre. The 214-square-metre property offers a spacious four-bedroom, three-bathroom layout sleeping up to 31 guests, complete with a fully equipped kitchen, Wi-Fi, private parking, air conditioning, and a garden.
9.4 44 reviews
Bolton
21/06 – 24/06
$509/nighttotal: $1527 (3 )
Luxury 4-bedrooms Home…
4 2
apartment , Toronto
This four-bedroom flat is located in Brampton, just a short drive (around 30km) from Toronto's attractions, including Vaughan Mills Shopping Centre, Canada's Wonderland, and Aviva Centre. The property has consistently received excellent ratings for cleanliness, location, and overall user experience. The spacious 167 square metre apartment comfortably accommodates up to eight guests and offers a fully equipped kitchen, a private patio, a balcony, free parking, and free Wi-Fi. Enjoy relaxing in the living area with a flat-screen TV and cable channels, or take advantage of the modern amenities, including air conditioning, a washing machine, a walk-in shower, and a bath.
Bolton
20/06 – 27/06
$2238/nighttotal: $15666 (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.
Best pet friendly Bolton vacation rentals
Among the 20 accommodations in Bolton, here are the 4 best pet friendly rentals
Bolton
20/06 – 27/06
$507/nighttotal: $3549 (7 )
Four Bedroom House Walking Distance From Downtown
1 2
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
20/06 – 27/06
$1356/nighttotal: $9492 (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
21/06 – 24/06
$350/nighttotal: $1050 (3 )
2br Suite | Near Pearson | Full Kitchen | Netflix
2 2
apartment , Toronto
This Brampton flat, situated 24km from Pearson International Airport and with easy access to Toronto's city centre and Niagara Falls, offers a convenient base for exploring the Greater Toronto Area. The 75-square-metre property features two bedrooms, one bathroom, sleeps six guests, and includes a fully equipped kitchen, laundry facilities, and a 65-inch Smart TV; nearby attractions include Canada's Wonderland and Vaughan Mills shopping mall.
9.1 14 reviews
Bolton
01/09 – 30/09
$273/nighttotal: $7917 (29 )
The Gore Retreat
1 2
apartment , Caledon East
This spacious four-bedroom house in Caledon East offers stunning country views and is situated approximately 48km from Toronto Pearson Airport and a short drive from Bolton and Brampton. The 5-bed property sleeps eight guests, boasts a large deck, microwave, dishwasher, air conditioning, parking, internet access, and is available for outdoor event rentals during warmer months.