Discover Your Perfect Milton Vacation Homes

Best Vacation Homes in Milton

Apartment
Map-icon
like-icon10.0
Exceptional
(13 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $95/Night 7 Nights - US $665
House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
1 Bedroom 1 Bath 2 Guests 301.39 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $233/Night 7 Nights - US $1,633
Hotel
Map-icon
like-icon8.6
Fabulous
(1074 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
US $107/Night 7 Nights - US $750
Apartment
Map-icon
like-icon10.0
Exceptional
(12 Reviews)
2 Bedrooms 1 Bath 4 Guests 1250 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $116/Night 7 Nights - US $811
star-icons-4
Apartment
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 2 Guests 645.83 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
US $104/Night 7 Nights - US $725
Apartment
Map-icon
like-icon10.0
Exceptional
(10 Reviews)
1 Bedroom 1 Bath 5 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
US $84/Night 7 Nights - US $587
Apartment
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $146/Night 7 Nights - US $1,024
Apartment
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $78/Night 7 Nights - US $543

Milton Luxury Rentals

Other
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4 Bedrooms 2 Baths 16 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
US $2,353/Night 7 Nights - US $16,469
Other
Map-icon
like-icon7.4
Very Good
(3 Reviews)
3 Bedrooms 2 Baths 9 Guests 2500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $2,252/Night 7 Nights - US $15,764
House
Map-icon
6 Bedrooms 4 Baths 15 Guests
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
More amenities
US $1,044/Night 7 Nights - US $7,310
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
6 Bedrooms 3 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $763/Night 7 Nights - US $5,344
House
Map-icon
like-icon3.0
Average
(2 Reviews)
4 Bedrooms 2 Baths 10 Guests 2600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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US $589/Night 7 Nights - US $4,126
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House
Map-icon
4 Bedrooms 4 Baths 15 Guests 2098.96 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $554/Night 7 Nights - US $3,881
Cottage
Map-icon
like-icon9.4
Exceptional
(6 Reviews)
5 Bedrooms 4 Baths 10 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $508/Night 7 Nights - US $3,556
House
Map-icon
5 Bedrooms 3 Baths 14 Guests 4000 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $432/Night 7 Nights - US $3,025

Milton Pet Friendly Vacation Rentals

Apartment
Map-icon
like-icon9.0
Exceptional
(4 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $99/Night 7 Nights - US $694
star-icons-4
Apartment
Map-icon
like-icon9.7
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 5 Guests 1076.39 ft²
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
More amenities
US $68/Night 7 Nights - US $476
Apartment
Map-icon
2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $122/Night 7 Nights - US $854
Apartment
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2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $200/Night 7 Nights - US $1,397
House
Map-icon
like-icon8.5
Fabulous
(2 Reviews)
1 Bedroom 2 Baths 10 Guests 2604.87 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
US $259/Night 7 Nights - US $1,815
House
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
4 Bedrooms 2 Baths 8 Guests 2200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $329/Night 7 Nights - US $2,303
House
Map-icon
like-icon8.0
Excellent
(1 Review)
5 Bedrooms 2 Baths 10 Guests 2600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $273/Night 7 Nights - US $1,912
House
Map-icon
like-icon8.0
Excellent
(1 Review)
3 Bedrooms 2 Baths 9 Guests
  • Pet Friendly
    Pet Friendly
  • Kitchen
    Kitchen
More amenities
US $200/Night 7 Nights - US $1,398

Milton Large Vacation Homes

Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
5 Bedrooms 2 Baths 9 Guests 2400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $299/Night 7 Nights - US $2,094
star-icons-4
Villa
Map-icon
like-icon9.5
Exceptional
(4 Reviews)
3 Bedrooms 3 Baths 6 Guests 1700.7 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
US $356/Night 7 Nights - US $2,494
House
Map-icon
5 Bedrooms 2 Baths 10 Guests 2300 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $396/Night 7 Nights - US $2,774
New
House
Map-icon
like-icon9.0
Exceptional
(2 Reviews)
6 Bedrooms 5 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
More amenities
US $71/Night 7 Nights - US $499
House
Map-icon
3 Bedrooms 2 Baths 90 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Parking
    Parking
More amenities
US $150/Night 7 Nights - US $1,052
House
Map-icon
like-icon9.8
Exceptional
(34 Reviews)
4 Bedrooms 3 Baths 10 Guests
  • Private Pool
    Private Pool
  • Spa
    Spa
More amenities
US $682/Night 7 Nights - US $4,774
House
Map-icon
like-icon8.0
Excellent
(1 Review)
4 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $810/Night 7 Nights - US $5,672
House
Map-icon
like-icon8.0
Excellent
(1 Review)
4 Bedrooms 3 Baths 13 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $462/Night 7 Nights - US $3,236

Discover & compare premier experiences around Milton

We understand the importance of quality and reliability in your travel experiences. That's why we've curated options from the most reputable tour and activity providers globally, ensuring you have access to top-tier adventures.

Why Choose Rent By Owner for your Milton Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Milton

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can enhance your experience by aligning with the region’s mild climate and local events, ensuring you enjoy your stay to the fullest while exploring the destination’s unique charm.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you can enjoy warm weather ideal for outdoor activities and exploring the natural beauty of the region. This is the most popular time to visit, so booking early ensures you secure a comfortable vacation rental.

Average Temperature Daytime: around 25°C - Nighttime: about 15°C
autumn
Fall (September to November)

The autumn season offers stunning foliage and mild temperatures, making it a desirable time for sightseeing and outdoor adventures in this destination. The pleasant climate draws many travelers seeking a scenic escape.

Average Temperature Daytime: approximately 20°C - Nighttime: roughly 10°C

Off-Season Highlights

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Winter (December to February)

In winter, the area transforms into a peaceful retreat with colder temperatures perfect for enjoying the quiet charm of the region. Booking a vacation rental now allows you to experience the serene side of here without the crowds.

Average Temperature Daytime: -2°C - Nighttime: -10°C
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Spring (March to May)

Spring brings milder weather and blooming landscapes, offering a refreshing time to explore the region's natural scenery. Off-peak rates make it an attractive option for those seeking a tranquil getaway.

Average Temperature Daytime: around 12°C - Nighttime: about 3°C

Weekly Weather Forecast for Milton

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or deck for relaxing and dining al fresco.
  • Benefit from access to a lush backyard or garden area perfect for outdoor gatherings.
  • Take advantage of outdoor grilling facilities to prepare meals in the fresh air.
  • Make use of nearby parks or open spaces ideal for walking, jogging, or picnicking.
  • Experience the convenience of provided bicycles for exploring local trails and scenic routes.
  • Relax in a landscaped yard with seating areas designed for enjoying the regional climate.
  • Utilize available parking spaces within outdoor settings for easy access during your stay.
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Family Activities

  • Wild Waterworks Park: Dive into family fun at this popular water park, perfect for cooling off and enjoying the sun during your stay here.
  • Kelso Conservation Area: Explore scenic hiking trails, enjoy a picnic, or admire stunning views of the river in this outdoor haven near the region.
  • Milton Education Centre and Museum: Engage with local history and discover educational exhibits that entertain and inform children and adults alike in this nearby cultural spot.
  • Rattlesnake Point Conservation Area: Experience breathtaking vistas and take part in outdoor activities like rock climbing and hiking suitable for family adventures in the area.
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Adult Activities

  • Explore the Milton Farmers' Market: Enjoy browsing fresh local produce and artisanal goods at this vibrant market, a perfect way to experience community life here.
  • Visit the Rattlesnake Point Conservation Area: Take in stunning views and indulge in hiking or rock climbing amidst natural beauty that highlights the area's outdoor appeal.
  • Discover the Milton Historical Museum: Dive into the region's rich heritage and learn about its development through engaging exhibits and displays.
  • Relax at Kelso Lake and Beach: Unwind by the water with activities like kayaking or simply soaking up the sun at this popular lakeside destination here.

Milton Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Shopping: Take advantage of the area's vibrant local markets and eateries to immerse yourself in the regional flavors and craftsmanship.
  • Visit Outdoor Parks and Trails: Make the most of the natural beauty here by exploring scenic parks and walking or biking along the region’s well-maintained trails.
  • Plan Your Trip Around Seasonal Events: Check the local event calendar to experience seasonal festivals and activities that highlight the area's community spirit.
  • Choose Strategic Accommodation Locations: Opt for vacation rentals situated near key attractions and public transportation to maximize your convenience during your stay.

Transportation Options

  • Milton Transit: This local bus service offers convenient transportation within the area, making it easy for you to explore Milton without a car.
  • GO Transit: Connecting here to larger regional hubs, GO Transit provides commuter rail and bus options for traveling to Toronto and beyond.
  • taxis and Rideshare Services: Ridesharing apps and local taxi services provide flexible and direct transportation around the region and to nearby attractions.
  • Car Rentals: Renting a vehicle gives you the freedom to visit surrounding parks, lakes, and other destinations at your own pace in this part of Ontario.

Local Customs Options

  • Local Festivals and Community Events: Participating in the area's seasonal festivals and community gatherings offers an authentic way to experience the region's vibrant culture during your stay.
  • Respect for Nature and Outdoor Etiquette: Observing proper outdoor etiquette when exploring parks and natural reserves ensures you honor the region’s commitment to preserving its scenic beauty.
  • Traditional Dining Customs: Embracing local dining etiquette, such as table manners and sharing dishes, allows you to enjoy authentic culinary experiences in this destination.
  • Greetings and Social Interactions: Familiarizing yourself with customary greetings and polite gestures helps foster friendly interactions with residents here.

Milton Vacation Rental Frequently Asked Questions

2. How many vacation rentals have private pools in Milton?

3. Which vacation homes in Milton are best for families?

If you are looking for a family-friendly vacation home in Milton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Milton:

4. How many Rentbyowner vacation rentals are available in Milton?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 252 in the Milton area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Milton. 

5. What is the cancellation policy for vacation rentals in Milton, Ontario?

The cancellation policies vary depending on the specific property listing. You should review the terms outlined on the property's page or contact the property owner directly to understand the cancellation timeframe and any associated fees.

6. How do I confirm availability and make a reservation in Milton's vacation rentals?

Availability can be checked directly through the listing. Once you find a suitable property, you can proceed with the booking by following the booking process provided, which typically includes contacting the owner or completing an online reservation form.

7. Are there any additional fees or deposits required when booking a vacation rental here?

Additional fees such as cleaning fees, security deposits, or service charges are often listed on the property page. It's recommended to review these details carefully or reach out to the host to clarify any extra costs before finalizing your reservation.

8. What amenities are usually included with vacation rentals in the area?

Most vacation rentals in this destination come equipped with essential amenities like Wi-Fi, parking, and kitchen facilities. However, specific features may vary, so it’s best to check each listing for detailed information about what is included during your stay.

9. What should I know about check-in and check-out procedures for these rentals?

Check-in and check-out times are determined by the property owner and are typically outlined in the listing. For a smooth arrival and departure experience, review these details ahead of time or contact the owner if you have any questions.

Milton Top Rated Vacation Rentals

star-icons-3
Hotel
Map-icon
like-icon8.6
Fabulous
(1003 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $122/Night 7 Nights - US $856
star-icons-3
Hotel
Map-icon
like-icon8.4
Excellent
(496 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $107/Night 7 Nights - US $747
Hotel
Map-icon
like-icon7.9
Very Good
(358 Reviews)
4 Baths
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $177/Night 7 Nights - US $1,239
star-icons-3
Hotel
Map-icon
like-icon7.9
Very Good
(190 Reviews)
4 Baths 243.26 ft²
  • Private Pool
    Private Pool
  • Skiing
    Skiing
More amenities
US $224/Night 7 Nights - US $1,569
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Hotel
Map-icon
like-icon7.8
Very Good
(284 Reviews)
1 Bath 281.21 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $112/Night 7 Nights - US $785
House
Map-icon
1 Bedroom 1 Bath 2 Guests 269 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $130/Night 7 Nights - US $910
Apartment
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $88/Night 7 Nights - US $618
House
Map-icon
like-icon5.4
Average
(3 Reviews)
3 Bedrooms 3 Baths 6 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $724/Night 7 Nights - US $5,066