Holiday rentals in Essa

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Top-rated holiday rentals in Essa

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

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Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 213 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...

12–19 Nov

$163 SGD per night

Guest favourite

Guest house in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

15–22 Aug

$191 SGD per night

Guest favourite

Flat in Egbert

4.91 out of 5 average rating, 45 reviews

Lovely one bedroom guest suite in the country

Looking for a quiet, country get away? We offer 1 bed, 1 bath guest suite with fireplace. Furnished, attached to host house, separate entrance Equipped with books, games, TV, semi-stocked kitchen, coffee/hot chocolate bar, deck, gazebo and field for walking Simcoe County/Bruce Trails close to hike, x-country ski, bike, dirt bike, ATV. Beaches within driving distance. 15 min to Barrie/Alliston for all amenities, Snow Valley Ski. 45 min in any direction to TO, Blue Mt, Mt St Louis, Wasaga, Muskoka

10–17 Aug

$170 SGD per night

Guest favourite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 191 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

14–21 Oct

$187 SGD per night

Guest favourite

Loft in Barrie

4.95 out of 5 average rating, 190 reviews

The Penthouse | Luxury at the Lake

Live the good life at 'The Penthouse' on Lake Simcoe. This is a luxurious and historical loft with stunning views of the bay. It's beautiful, bright, clean and spacious - perfect for romance and adventure with friends. Steps to the sandy beach, waterfront trails and the heart of downtown. Enjoy a meal downstairs at the legendary 'Farmhouse Restaurant'. Perfect all-in-one wedding venue, room to get ready and a party downstairs. If you're looking to unwind or a night on the town, it's all yours!

7–14 Jul

$224 SGD per night

Guest favourite

Home in Barrie

4.94 out of 5 average rating, 49 reviews

Tranquility Haven

Stylish Ambiance: Our space is a basement thoughtfully designed to provide you comfort. Spacious Comfort: Relax and unwind with plenty of room to stretch in our Family-Friendly space Central Location: Enjoy easy access to dining and shopping options minutes away. Outdoor Adventures: Adventure awaits with lakes, beaches, and skiing sites in close proximity. Book your stay with us today and experience the best of Barrie. We invite you to enjoy the peace, style, and natural beauty that awaits you

27 Jun – 4 Jul

$136 SGD per night

Guest favourite

Guest house in Angus

4.98 out of 5 average rating, 140 reviews

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to your private oasis! Our 600 sq/ft bachelor suite offers a clean and cozy retreat. Relax and unwind in the hot tub or with WIFI, Netflix & Prime TV. Just a 2-min drive to restaurants and groceries. CFB Borden & the North Trillium Trail within 5-min. Looking for more R&R? Discover Scandinavia Spa or Vetta Nordic Spa, both within 40-min. Barrie, Creemore, & Wasaga Beach are all within 30-mins, while Collingwood & Blue Mountain are just 40 min. Book now for your ultimate getaway!

16–23 Jun

$115 SGD per night

Guest favourite

Farm stay in Essa

5.0 out of 5 average rating, 118 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!

2–9 Dec

$239 SGD per night

Guest favourite

Flat in Wasaga Beach

4.95 out of 5 average rating, 338 reviews

The Upper Deck

The upper deck is an amazing one bedroom studio with a full newly renovated bathroom, a sweet kitchenette, an amazing king size bed, a 65 “ inch HD smart Samsung TV with a live edge counter- a great workspace or eating area. One wall is floor to ceiling windows -lots of great natural light!!! Outdoors has an amazing hot tub , rustic firepit area , a beautiful covered outdoor eating area with Bbq and you can hear the lake!! Note- the studio is a separate but is part of a house.

8–15 Oct

$175 SGD per night

Guest favourite

Barn in Utopia

4.89 out of 5 average rating, 37 reviews

Country Solitude

Brand New Barn, set on family farm land that dates back to 1845. The upper level living space is open concept that has everything you need for a relaxing time. A 10 minute drive from downtown Barrie and 10-30 minutes from multiple ski resorts, steps from endless snowmobile & hiking trails. You will have the peace and privacy of country living set in quiet comfort. The apartment faces west towards Niagara escarpment which provides outstanding views and sunsets.

7–14 Mar

$137 SGD per night

Guest favourite

Flat in Innisfil

4.99 out of 5 average rating, 495 reviews

Cozy One bedroom Apartment by the Lake

A clean and inviting upper level one-bedroom apartment across the street from beautiful Lake Simcoe & Innisfil Beach Park! A short walk to all amenities in town, (Tim's, LCBO, Pizza, Nofrills, Canadian Tire & More) just 20 minutes to Barrie and 50 minutes to Toronto. This apartment is perfect for a summer weekends to the beach. Also ideal for ice fishing in winter. You have your own private outdoor space with a BBQ and plenty of parking for car & boat.

8–15 Oct

$103 SGD per night

Guest favourite

Flat in Angus

5.0 out of 5 average rating, 23 reviews

New Two Bedroom Entire Basement Apartment in Angus

Spacious two-bedroom and one-bathroom basement apartment in Angus. Guests will have access to a fully stocked kitchen, washer/dryer, free high-speed internet 1000mbps & smart TV with popular streaming services. All popular stores and amenities are nearby within five minutes. - 3 min to restaurants and groceries - 5 min to River & Fishing - 5 min to CFB Borden - 5 min to Trillium Trail - Different Ski resorts around 15 to 40 min

10–17 Feb

$103 SGD per night