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Vacation rentals in Bolton

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Top-rated vacation rentals in Bolton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite in Vaughan

4.93 out of 5 average rating, 608 reviews

Luxury Modern Two Bedrooms Basement Apartment

No 3rd party booking! No parties! No visitors! Tons of upgrades and high end modern features! High ceiling above grade basement unit. Open concept living space include fireplace, smart TV, full kitchen, laundry and large wardrobe 1 parking Enjoy scenic trails in Woodbridge 10min to Vaughan Mills outlets & Canada's wonderland 15min to Pearson airport 24hr Exterior Surveillance. One camera over looking driveway. One camera above the front door and one outside the storm door to the Airbnb unit

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 294 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Home in Vaughan

4.99 out of 5 average rating, 209 reviews

Cozy One-Bedroom Retreat in Vaughan, ON

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, and transit. Smoke- and pet-free space

Guest suite in Kleinburg

4.92 out of 5 average rating, 133 reviews

Walkout Guest Suite in Vaughan

Fully furnished, luxury, legal, two bedrooms basement apartment with new appliances and beds. The apartment has a private wide entrance to the backyard, south facing, sunny, with natural gas fireplace, air condition, and wood subflooring for comfort, private washer, dryer, dishwasher, stove, kitchen appliances, and fridge. It is close to Kleinburg Humber River Trail, McMichael Art Gallary, and not too far from Vaughan Mills and Canada Wonderland. Easy access to Toronto pearson Int'l Airport.

Tiny home in Acton

4.98 out of 5 average rating, 272 reviews

Farmview Sunrise Cabin located at Molinaro Ranch

Welcome to our Farmview Sunrise tiny cabin that are nestled in the middle of our private oasis located in Acton ON. Our 50 acre farm has spectacular views from every direction. Our horses, longhorn cattle, swans and miniature goats are here to greet you as well. This unique space will allow you to enjoy the beautiful outdoors during the day and a cozy warm space in the evenings. Breakfast fixings are included. Our in house chef is happy to accommodate vegan/plant based meals as well.

Guest suite in Orangeville

4.92 out of 5 average rating, 706 reviews

Headwaters Retreat - HotTub & Cozy Fireplace Suite

Escape to our cozy and rustic queen suite with a modern touch and hottub right at your door. Private entrance overlooking our peaceful conservation area. Spacious fireplace in main suite with ensuite bathroom, Apple TV, steaming option and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Farm stay in Essa

4.99 out of 5 average rating, 165 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Guesthouse in Orangeville

4.96 out of 5 average rating, 123 reviews

A bright & stylish urban studio

Come & relax...in privacy. The "Carriage House" is a 634 square foot studio-style unit is unique & intimate. You will be away from the main house, in your own building. Amazing kitchen, complete with gas range. Spacious & elegant over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for your convenience. Diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Guest suite in Schomberg

4.92 out of 5 average rating, 453 reviews

Romantic Country Suite for Couples with King Bed

Our Country Suite is all about Rustic Elegance. Come to our farm for a night, a weekend, or longer. Perfect place for a quiet, peaceful & relaxing weekend escape or a romantic getaway. You’ll love our rural location, full kitchen, wifi internet, 55" 4K Smart TV, three piece bathroom, laundry, propane BBQ, Patio access to propane fire pit. Enjoy walking trails in our bush, biking, close to nature and much more. Located about 50 min. from Toronto.

Guest suite in Caledon

4.98 out of 5 average rating, 112 reviews

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway on 3 acres of land The suite is close to conservation areas Cheltenham Badlands, Fork of the Credit and Terra Cotta Bruce trail, golf courses, restaurants, bakeries, butchers, farm produce and city needs are close Each season is wonderful Spring/summer has lush forests, the pond and fire pit Fall walks with the beautiful colours Winter has a white blanket and access to winter sports

Tiny home in Schomberg

4.89 out of 5 average rating, 277 reviews

HONE Retreat - An Honest Designed Tiny House

Experience a retreat to the country and a beautifully effective space. Designed as an experiment in creating the perfect get away space that could be taken off-grid. Within the space is a kitchen (stovetop, wall oven, double sink & fridge), full washroom (a beautiful cedar shower, sink, custom composting toilet & mirror), washing machine, radiant heating, AC & loft sleeping space with king bed and a skylight to view the stars!

Guest suite in Orangeville

5 out of 5 average rating, 120 reviews

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. Newly renovated 1 bdrm apartment located downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Bolton vacation rentals

Free parking on premises

Air conditioning

Stay near Bolton's top sights

Pizzaville12 locals recommend

Symposium Cafe Restaurant & Lounge10 locals recommend

Landmark Cinemas Caledon, Bolton5 locals recommend

Garden Foods Ltd5 locals recommend

Cold Creek Conservation Area4 locals recommend

Walmart Supercentre3 locals recommend

Other great vacation rentals in Bolton

Shipping container in Caledon

4.91 out of 5 average rating, 33 reviews

High Meadows Escape

Rental unit in Caledon

5 out of 5 average rating, 17 reviews

The Luxe Hideout - Guest Suite Basement Apartment

Dome in Utopia

4.93 out of 5 average rating, 67 reviews

Glamping Dome Riverview Utopia

Rental unit in Schomberg

5 out of 5 average rating, 20 reviews

Mill Dam Inn

Home in Kleinburg

4.88 out of 5 average rating, 86 reviews

Spacious 2-Bedroom Unit-Close to YYZ Airport

Farm stay in Loretto

4.95 out of 5 average rating, 43 reviews

Character-filled farm guest house on 8 acres

Rental unit in Brampton

4.9 out of 5 average rating, 30 reviews

Stylish Retreat | Luxe Comfort | Cozy Queen Beds

Home in Kleinburg

5 out of 5 average rating, 45 reviews

Charming Log Home - 25 private acres in Caledon

Quick stats about vacation rentals in Bolton

Total rentals
20 properties
Total number of reviews
420 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Frequently Asked Questions

What are the most popular amenities for House Rentals in Bolton?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Bolton?
Bolton has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Bolton have free parking?
Absolutely! We offer over 10 house rentals with free parking in Bolton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Bolton have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Bolton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Bolton have wifi?
Absolutely! We offer over 10 house rentals with wifi in Bolton. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Bolton?
Yes! Work meets play with ease at over 10 vacation rentals in Bolton featuring dedicated workspaces. Stay connected and productive in your home away from home.

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