Discover Your Perfect Chelmsford Vacation Homes

Best Vacation Homes in Chelmsford

Bed & Breakfast
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
1 Bedroom 1 Bath 3 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R1,016/Night 7 Nights - R7,113
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Apartment
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like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 2 Guests 4305.56 ft²
  • Parking
    Parking
  • Internet
    Internet
More amenities
R2,280/Night 7 Nights - R15,963
Hotel
Map-icon
like-icon8.8
Fabulous
(960 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Breakfast
    Breakfast
More amenities
R2,146/Night 7 Nights - R15,020
House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
2 Bedrooms 1 Bath 5 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
R3,147/Night 7 Nights - R22,034
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Apartment
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like-icon9.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 2 Guests 495.14 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R2,361/Night 7 Nights - R16,525
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
R3,436/Night 7 Nights - R24,052
Apartment
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like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 3 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
R2,981/Night 7 Nights - R20,876
Cabin
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 6 Guests 400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
R2,379/Night 7 Nights - R16,658

Chelmsford Luxury Rentals

Hotel
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1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
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R13,795/Night 7 Nights - R96,571
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Hotel
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like-icon7.6
Very Good
(1480 Reviews)
4 Baths 548.96 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R8,089/Night 7 Nights - R56,622
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
6 Bedrooms 3 Baths 14 Guests 3500 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R7,957/Night 7 Nights - R55,696
New
House
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3 Bedrooms 1 Bath 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R6,014/Night 7 Nights - R42,099
House
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like-icon9.2
Exceptional
(11 Reviews)
4 Bedrooms 2 Baths 8 Guests 1500 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R4,940/Night 7 Nights - R34,589
Apartment
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3 Bedrooms 4 Baths 6 Guests
  • Kitchen
    Kitchen
  • Parking
    Parking
More amenities
R4,908/Night 7 Nights - R34,357
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Cabin
Map-icon
like-icon7.1
Very Good
(90 Reviews)
24 Bedrooms 1 Bath 6 Guests 301.39 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R4,797/Night 7 Nights - R33,580
New
Apartment
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3 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
R4,359/Night 7 Nights - R30,520

Chelmsford Pet Friendly Vacation Rentals

Apartment
Map-icon
like-icon9.6
Exceptional
(14 Reviews)
1 Bedroom 1 Bath 4 Guests 1100 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R1,423/Night 7 Nights - R9,958
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Apartment
Map-icon
like-icon8.5
Fabulous
(4 Reviews)
1 Bedroom 1 Bath 4 Guests 495.14 ft²
  • View
    View
  • Pet Friendly
    Pet Friendly
More amenities
R1,084/Night 7 Nights - R7,593
Apartment
Map-icon
like-icon3.0
Average
(2 Reviews)
3 Bedrooms 1 Bath 10 Guests
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
R3,119/Night 7 Nights - R21,835
House
Map-icon
like-icon8.6
Fabulous
(21 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Pet Friendly
    Pet Friendly
  • Kitchen
    Kitchen
More amenities
R2,900/Night 7 Nights - R20,297
Apartment
Map-icon
like-icon8.0
Excellent
(1 Review)
1 Bedroom 1 Bath 2 Guests 495.14 ft²
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
More amenities
R2,676/Night 7 Nights - R18,742
Apartment
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2 Bedrooms 1 Bath 5 Guests 700 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R2,748/Night 7 Nights - R19,238
Apartment
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1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R1,813/Night 7 Nights - R12,688
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests 400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R1,798/Night 7 Nights - R12,588

Chelmsford Large Vacation Homes

House
Map-icon
like-icon8.8
Fabulous
(3 Reviews)
5 Bedrooms 2 Baths 8 Guests 2000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R4,292/Night 7 Nights - R30,040
Apartment
Map-icon
like-icon7.1
Very Good
(73 Reviews)
70 Bedrooms 1 Bath 5 Guests 796.53 ft²
  • Skiing
    Skiing
  • Kitchen
    Kitchen
More amenities
R1,224/Night 7 Nights - R8,569
House
Map-icon
like-icon7.6
Very Good
(5 Reviews)
5 Bedrooms 1 Bath 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R4,173/Night 7 Nights - R29,213
Villa
Map-icon
like-icon6.8
Good
(9 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R1,213/Night 7 Nights - R8,486
Apartment
Map-icon
like-icon6.0
Good
(2 Reviews)
2 Bedrooms 1 Bath 10 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R2,782/Night 7 Nights - R19,470
House
Map-icon
like-icon9.0
Exceptional
(6 Reviews)
3 Bedrooms 2 Baths 10 Guests 2600 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
R8,620/Night 7 Nights - R60,344
Apartment
Map-icon
like-icon4.0
Average
(5 Reviews)
3 Bedrooms 1 Bath 10 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R3,953/Night 7 Nights - R27,674
Apartment
Map-icon
like-icon4.0
Average
(3 Reviews)
5 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R6,233/Night 7 Nights - R43,621

Why Choose Rent By Owner for your Chelmsford 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 Chelmsford

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can enhance your experience, so consider planning your trip during the region’s most favorable seasons to enjoy optimal weather and local events in Chelmsford, Ontario, Canada.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you can enjoy longer daylight hours and pleasant weather, making this an ideal time to explore the region around Chelmsford through outdoor activities or relaxation at your vacation rental.

Average Temperature Daytime: around 24°C (75°F) - Nighttime: approximately 14°C (57°F)
autumn
Fall (September to November)

Autumn brings vibrant foliage and mild temperatures, providing a scenic backdrop for your stay and an excellent opportunity to experience the area's natural beauty during this popular season for visitors seeking a peaceful retreat.

Average Temperature Daytime: around 15°C (59°F) - Nighttime: approximately 5°C (41°F)

Off-Season Highlights

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Winter (December to February)

The winter months offer a quieter period with cooler weather, perfect for those who prefer a tranquil escape and don’t mind bundling up while enjoying the serene snowy landscape around here.

Average Temperature Daytime: -5°C (23°F) - Nighttime: -15°C (5°F)
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Spring (March to May)

As the region transitions from winter to summer, spring features moderate temperatures and blooming scenery, making it a less crowded time to find cozy vacation rentals and experience peaceful surroundings.

Average Temperature Daytime: about 10°C (50°F) - Nighttime: around 0°C (32°F)

Weekly Weather Forecast for Chelmsford

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

  • You can enjoy a spacious outdoor area with private patios or decks to relax and unwind.
  • Many properties feature lush gardens or landscaped yards perfect for outdoor gatherings.
  • Expect amenities such as grills or barbecue stations to enhance your outdoor cooking experience.
  • Access to outdoor fire pits or fireplaces provides cozy evenings under the stars.
  • There are often options for outdoor recreational activities like nearby hiking trails or walking paths.
  • You might find outdoor furniture, including loungers and dining sets, to make the most of the fresh air.
  • Some rentals include direct access to waterfronts or lakes for boating, swimming, or fishing in the region.
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Family Activities

  • Laurentian Ski Hill: Experience family-friendly winter activities, including downhill skiing and snowboarding, perfect for enjoying the snowy landscapes here during the winter months.
  • Lake Laurentian Conservation Area: Explore scenic trails and picnic spots at this natural reserve, offering a peaceful retreat suitable for outdoor adventures with kids.
  • Discovery North: Discover interactive exhibits and engaging science displays designed to inspire curiosity and learning for children of all ages in the region.
  • New Liskeard Golf Course: Enjoy a relaxing day on the links at this nearby golf course, ideal for family outings and beginner-friendly golfing experiences.
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Adult Activities

  • Exploring Local Nature Reserves: Discover the region’s natural beauty through scenic walks and birdwatching at nearby nature reserves, perfect for outdoor enthusiasts staying in Chelmsford.
  • Enjoying the Regional Trails: Take advantage of well-maintained trails that wind through this destination, offering a peaceful setting for hiking or cycling amidst the area's lush landscape.
  • Visiting Cultural Spots: Immerse yourself in local history and art by exploring cultural landmarks and galleries that showcase the region’s unique heritage.
  • Participating in Outdoor Recreation: Engage in activities such as fishing or picnicking at popular outdoor spots, ideal for relaxing days during your stay here.

Chelmsford Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Outdoor Activities: Take advantage of the region’s natural scenery by engaging in outdoor pursuits such as hiking, fishing, or kayaking, which are easily accessible from your vacation rental here.
  • Visit Community Events: Check out local festivals or markets to immerse yourself in the area's culture and connect with residents during your stay in this destination.
  • Plan Your Meals Strategically: Opt for accommodations close to dining options or prepare meals at your rental to enjoy fresh local ingredients and save time exploring.
  • Discover Nearby Attractions: Use your vacation rental as a comfortable base to explore nearby sites, ensuring you maximize your time and experience the best this part of Ontario has to offer.

Transportation Options

  • Public Transit: The area is served by local bus services, providing an affordable and convenient way to explore nearby attractions and amenities.
  • Taxis and Rideshare Services: Taxis and rideshare options like Uber are widely available here, offering flexible transportation for your trips around the region.
  • Car Rentals: Several car rental agencies operate nearby, giving you the freedom to explore this destination and its surroundings at your own pace.
  • Bike Rentals: For eco-friendly travel or a leisurely experience, bike rentals are accessible in the area, ideal for navigating local paths and scenic routes.

Local Customs Options

  • Ontario Hospitality:** You’ll notice a warm and welcoming attitude towards visitors, reflecting the region's friendly community spirit.
  • Local Cuisine Etiquette:** Sharing meals at communal gatherings is common here, and it’s polite to participate in these traditions with gratitude and appreciation.
  • Respect for Nature:** The area's natural beauty encourages eco-friendly practices and respect for outdoor spaces during your stay.
  • Cultural Celebrations:** Attending seasonal festivals and events offers insight into regional customs and traditions unique to this part of Ontario.

Frequently Asked Questions About Chelmsford?

1. What are the top vacation rentals in Chelmsford?

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

There are 1 vacation rentals with private pools near Chelmsford. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 156 in the Chelmsford 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 Chelmsford. 

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

Cancellation policies vary depending on the property owner and listing details. You should review the specific rental's cancellation terms listed on the property page or contact the host directly for clarification.

6. How do I ensure my booking in Chelmsford complies with local regulations?

To comply with local regulations, carefully read the listing description and house rules provided by the host. If you have questions, reaching out directly to the property owner can help clarify any requirements or restrictions.

7. Are there any additional fees when booking a vacation rental in this part of Ontario?

Additional fees such as cleaning, service charges, or security deposits are often itemized in the listing details. Always review the total cost during the booking process or contact the host for confirmation.

8. Can I get a custom stay experience in Chelmsford, Ontario, such as early check-in or late check-out?

Special requests like early check-in or late check-out depend on the host’s policies and availability. It’s best to communicate your needs directly with the property owner before confirming your reservation.

9. What amenities are typically included in vacation rentals here in Ontario?

Most listings will specify included amenities such as Wi-Fi, parking, kitchen facilities, and laundry options. To ensure the property meets your needs, review the amenities section or contact the host for detailed information.

Chelmsford Top Rated Vacation Rentals

star-icons-3
Hotel
Map-icon
like-icon8.6
Fabulous
(1223 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
R2,137/Night 7 Nights - R14,954
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Hotel
Map-icon
like-icon8.4
Excellent
(1002 Reviews)
1 Bath
  • Pool
    Pool
  • Kitchen
    Kitchen
More amenities
R2,126/Night 7 Nights - R14,888
Hotel
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like-icon7.8
Very Good
(1004 Reviews)
1 Bath
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R1,892/Night 7 Nights - R13,250
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Hotel
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like-icon7.4
Very Good
(341 Reviews)
7 Baths 316.77 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R2,467/Night 7 Nights - R17,270
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Hotel
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like-icon7.1
Very Good
(1817 Reviews)
9 Baths 271.49 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R1,978/Night 7 Nights - R13,845
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Hotel
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like-icon7.1
Very Good
(903 Reviews)
14 Baths 258.33 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R1,498/Night 7 Nights - R10,487
star-icons-4
Hotel
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like-icon7.0
Very Good
(529 Reviews)
13 Baths 235.27 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R1,382/Night 7 Nights - R9,677
Bed & Breakfast
Map-icon
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R1,247/Night 7 Nights - R8,734