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Tottenham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Tottenham vacation rentals

A deck with two white lounge chairs and a red railing overlooking a lake.

1. Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)
Loretto
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay, the place was clean and comfortable. Thank you so much."
Canada
Michael W.
$105 nightly
The price is $119
Sep 27 - Sep 28
Total with taxes and fees
Lakeside Private suite (Queen bed room)
A spacious hallway with a neutral color scheme, a beige sofa, and a shower area with a glass door.

2. Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
8.4 out of 10, Very good, (6 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
$174 nightly
The price is $197
Sep 28 - Sep 29
Total with taxes and fees
Clean & Cozy Home Near Downtown
A modern living room with a sofa, a TV, and large windows.

3. Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful

Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
Bond head
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and the host was very accommodating. One of the best places to stay in the area."
United States
A A.
$170 nightly
The price is $193
Oct 8 - Oct 9
Total with taxes and fees
Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

4. Lakeview private suite with kitchen (Twin or King)

Lakeview private suite with kitchen (Twin or King)
Loretto
8.6 out of 10, Excellent, (8 reviews)
"Beautiful spot to stay! Highly recommended "
United States
Patrick S.
$126 nightly
The price is $143
Oct 1 - Oct 2
Total with taxes and fees
Lakeview private suite with kitchen (Twin or King)
A backyard with a patio, a small shed, and a wooden fence.

5. Studio Apartment in the heart of Caledon

Studio Apartment in the heart of Caledon
CALEDON EAST
8.4 out of 10, Very good, (6 reviews)
"Beautiful flat !"
Canada
Jaivyn
$62 nightly
The price is $70
Oct 8 - Oct 9
Total with taxes and fees
Studio Apartment in the heart of Caledon
A modern kitchen with stainless steel appliances, a microwave, oven, and a refrigerator.

6. Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400

Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
Kettleby, King City
7.4 out of 10, Good, (3 reviews)
"Nice place"
Canada
mike
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

7. Resort style entire guesthouse with kitchen (2 rooms)

Resort style entire guesthouse with kitchen (2 rooms)
Loretto
5.4 out of 10, (3 reviews)
"Very easy check in "
Canada
Carly C.
$161 nightly
The price is $182
Sep 27 - Sep 28
Total with taxes and fees
Resort style entire guesthouse with kitchen (2 rooms)
A front-loading LG washer and dryer unit with a control panel, a digital display, and a vent hose.

8. Spacious | Private | Quiet | 2 BR Walkout Suite

Spacious | Private | Quiet | 2 BR Walkout Suite
Aurora
10.0 out of 10, Exceptional, (1 review)
"This property is an amazing, family-friendly retreat located in a peaceful, quiet neighborhood. The spacious unit is impeccably clean and features a fully equipped kitchen. The host provides outstanding, responsive service, making this an ideal choice for both short-term and long-term stays. Highly recommended."
Canada
Ayla
$258 nightly
The price is $292
Sep 28 - Sep 29
Total with taxes and fees
Spacious | Private | Quiet | 2 BR Walkout Suite
A two-story brick house with a patio area.

9. Entire place, Ground level walkout Basement with Huge backyard

Entire place, Ground level walkout Basement with Huge backyard
Orangeville
7.4 out of 10, Good, (40 reviews)
"This place needs lots of upgrades and no privacy at all. No blinds for the widows front door is unsecured. Needs more lights."
Canada
Nilantha
$104 nightly
The price is $118
Sep 30 - Oct 1
Total with taxes and fees
Entire place, Ground level walkout Basement with Huge backyard
A modern living room with a glass coffee table, two armchairs, a sofa, a wall-mounted neon sign, and a framed picture.

10. Bright 3BR Home with Balcony & Free Parking

Bright 3BR Home with Balcony & Free Parking
Bradford West Gwillimbury
Bright 3BR Home with Balcony & Free Parking
A modern hallway with wooden flooring, white walls, and a door leading to a room with a large window.

11. Luxury, Brand-New, Spacious , Modern Apartment with One Parking.

Luxury, Brand-New, Spacious , Modern Apartment with One Parking.
Richmond Hill
8.4 out of 10, Very good, (7 reviews)
"Host was very accommodating place was very clean and spacious bathroom and shower were absolutely perfect definitely will be back again!"
Canada
Keyonna G.
$118 nightly
The price is $133
Oct 8 - Oct 9
Total with taxes and fees
Luxury, Brand-New, Spacious , Modern Apartment with One Parking.
A modern kitchen with white cabinets, stainless steel appliances, and a black sink.

12. New, Clean and Comfortable Apartment with Private Entrance.

New, Clean and Comfortable Apartment with Private Entrance.
East Gwillimbury
9.0 out of 10, Wonderful, (12 reviews)
"easy to check in and a great place to stay! very helpful hosts."
United States
Kwame A.
$143 nightly
The price is $161
Oct 1 - Oct 2
Total with taxes and fees
New, Clean and Comfortable Apartment with Private Entrance.
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a bar stool.

13. Cozy Basement Apartment (700 sq ft) with Full Kitchen

Cozy Basement Apartment (700 sq ft) with Full Kitchen
Orangeville
9.0 out of 10, Wonderful, (2 reviews)
"Great location!"
Canada
Kefa
$100 nightly
The price is $113
Oct 17 - Oct 18
Total with taxes and fees
Cozy Basement Apartment (700 sq ft) with Full Kitchen
A modern living room with a dark sofa, light-colored ottomans, and a coffee table. There is a red armchair and a dining area with a table and chairs. The kitchen is visible in the background with white cabinets and appliances.

14. Spacious 2 BR, 3 beds, sleeps 6, kitchen, laundry

Spacious 2 BR, 3 beds, sleeps 6, kitchen, laundry
Richmond Hill
9.8 out of 10, Exceptional, (6 reviews)
"Great host! And very clean place"
Canada
KABIR
$190 nightly
The price is $214
Oct 8 - Oct 9
Total with taxes and fees
Spacious 2 BR, 3 beds, sleeps 6, kitchen, laundry
A two-story house with a garage, double doors, and a nameplate reading "247 Walter English Drive".

15. The Luxe Haven

The Luxe Haven
East Gwillimbury
$227 nightly
The price is $257
Sep 28 - Sep 29
Total with taxes and fees
The Luxe Haven

16. Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking

Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking
Aurora
10.0 out of 10, Exceptional, (15 reviews)
"My daughter and I stayed here for one week and we had the most amazing time. The owner answered all our questions so that everything went smoothly - from the moment of check-in to how to get to the neighbourhood grocery shop. This area was very safe and quiet and most of all, this very well-kept and welcoming place made our trip so memorable and pleasurable. She even shared her fresh baked croissants with us!! We are so satisfied to be able to stay here."
Canada
Hitomi
$133 nightly
The price is $151
Oct 6 - Oct 7
Total with taxes and fees
Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking
A wooden staircase with a handrail, leading to a landing with a chandelier.

17. Peaceful country home on 25 acres of wooded land

Peaceful country home on 25 acres of wooded land
Loretto
8.0 out of 10, Very good, (1 review)
"Check in was easy, the house was a good size to fit my party of 9. It would have been nice if some of the back yard grass was cut to play games and for my small dog. It would help to have a few more towels. The house was clean n comfortable."
Canada
Bev C.
$489 nightly
The price is $553
Sep 28 - Sep 29
Total with taxes and fees
Peaceful country home on 25 acres of wooded land
A spiral staircase with wooden handrails and carpeted steps.

18. Spacious 4BR Orangeville Home, Private Deck, Sleeps 10—Near Headwaters Hospital!

Spacious 4BR Orangeville Home, Private Deck, Sleeps 10—Near Headwaters Hospital!
Orangeville
$333 nightly
The price is $376
Sep 29 - Sep 30
Total with taxes and fees
Spacious 4BR Orangeville Home, Private Deck, Sleeps 10—Near Headwaters Hospital!
A living room with a gray sofa, a coffee table, and a painting of a coastal landscape.

19. Luxurious Spacious Dream Home with Parking!

Luxurious Spacious Dream Home with Parking!
Richmond Hill
8.8 out of 10, Excellent, (25 reviews)
"Large house great for our family and dog. Would stay again"
Canada
Sarah C.
$211 nightly
The price is $238
Oct 1 - Oct 2
Total with taxes and fees
Luxurious Spacious Dream Home with Parking!

20. Nice and clean cosy apartment basement

Nice and clean cosy apartment basement
Newmarket
$168 nightly
The price is $189
Oct 1 - Oct 2
Total with taxes and fees
Nice and clean cosy apartment basement
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Tottenham Hotel Reviews

Best Western Plus Orangeville Inn & Suites

Best Western Plus Orangeville Inn & Suites

10/10 Excellent
"Great, Clean place. I’d recommend it."
Christine 1-night trip
Posted 3 hours ago
Best Western Plus Orangeville Inn & Suites

Find out more about Tottenham

Everything you need to know about Tottenham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tottenham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tottenham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tottenham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tottenham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Tottenham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $133 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tottenham rentals

At Expedia, we put the best Tottenham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tottenham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tottenham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tottenham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Tottenham?

Yes, there are vacation rentals in Tottenham near South Simcoe Railway, or you can choose a secluded option if you're looking for extra privacy while you relax.

What are some of the best vacation rentals that Tottenham has to offer?

Large Estate with Luxury Collection of Amenities : Visitors like this Tottenham vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Tottenham?

While you're exploring the area, Albion Hills Conservation Area and Island Lake Conservation Area are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find South Simcoe Railway and Caledon Equestrian Park.

What’s a vacation rental in Tottenham like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in Tottenham. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.