Holiday rentals in Head Lake

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 384 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...

4.97 out of 5 average rating, 184 reviews

Treehouse in Huntsville

Muskoka A-Frame I HotTub, Pet-Friendly, Near Beach

Escape to our charming A-Frame TreeHouse nestled among Muskoka trees. Relax, disconnect and immerse yourself in this truly unique getaway. Whether you seek serenity or outdoor adventures like hiking, biking, SUP boarding or skiing, the Door25 TreeHouse offers the ideal blend of relaxation & adventure for a unforgettable escape from the city. Features: *Hot Tub & Fireplace *Pet-Friendly *Beautiful Views *Free Provincial Park Pass *10 Min Walk to Lake & Ski Hill 📷 Check us out @door25stays

4.99 out of 5 average rating, 121 reviews

Cottage in Bracebridge

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage with loft is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

5 out of 5 average rating, 185 reviews

Cabin in Bracebridge

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

4.86 out of 5 average rating, 307 reviews

Cabin in Reaboro

Cedar Springs Cabin - A Cozy Hideaway in the Woods

Tucked away between the hills of Reaboro Ontario, this 175+ year old pioneer log cabin has been brought back to life with the comfort of all new modern amenities, while still keeping the rich historic character of its past. The cabin homestead was crafted in 1847, before Canada was a country. With your significant other, family or friends, come cozy up to the fire, soak in the hot tub and enjoy swimming in the spring fed pond. Board games and movies are provided for your entertainment.

4.99 out of 5 average rating, 122 reviews

Island in Lakefield

Suite Island Retreat

We invite you to relax and recharge with this unique island glamping experience; a tiny lakefront cabin with modern touches. From your private dock, swim in the deep water, play on the floaty mat, lounge, read, paddle in the canoe, and catch -both- a sunrise and a sunset… absolute perfection. Amenities also include an outdoor kitchen and BBQ, a fire pit, an outdoor shower, and a clean and airy outhouse. Oh, and a lovely hammock, made for two! Come and enjoy! :) -Minimum 3 nights-

Tiny home in Minden Hills

4.91 out of 5 average rating, 222 reviews

A cozy cabin for intimate wilderness escape

An absolutely private site of a former hunting camp above a peaceful lake surrounded by a quiet forest. Three comfortable cabins on site, each with a screened porch, kitchenette, running water, and a tree-house-like sleeping loft, can accommodate up to six guests double occupancy. This completely private property has many trails to explore, comes with a canoe and a rowboat, and is perfect for people of all ages seeking adventure or a tranquil atmosphere to relax and rejuvenate.

4.98 out of 5 average rating, 131 reviews

Cabin in Baysville

Luxury cabin on private 60 acre forest in Muskoka

Disconnect and reconnect in nature at this unforgettable luxury off-grid cabin escape. The vibe is modern simplicity, with everything you need to truly relax in nature. Luxurious linens, kitchen essentials, and a curated selection of books invite you for a slow stay. The cabin runs on solar panels and is designed to stay warm in winter and cool in summer. Although there is wifi, we hope you forgo using it for stargazing at night or cozying up in front of the wood stove.

4.99 out of 5 average rating, 356 reviews

Yurt in Irondale

Tall Pines Nature Retreats ~ L’Orange

Reconnect with nature at Tall Pines Nature Retreats, where a luxurious hand-painted yurt with an indoor soaker tub offers comfort and calm in a forest sanctuary on a boutique horticultural farm. Stargaze by the fire, unwind beneath intricate ceiling art, or explore a magical riverside. Paddle, swim, or float with seasonal use of canoe, kayak, SUPs, or snowshoes. This is a registered agri-tourism farm offering a nature and wellness retreat—not a typical short-term rental.

Cottage in Kawartha Lakes

4.85 out of 5 average rating, 130 reviews

Year-Round Relaxation, a Modern Riverfront Cottage

Welcome to Somerville Lodge, a thoughtfully designed cottage with all the modern amenities you need to make the most of your relaxing getaway In Kawartha Lakes, under 2.5 hours from Toronto, our cottage sits on an acre of land along 350ft of the Burnt River, perfect for swimming, kayaking and paddle boarding. A large deck has space for lounging, or relax in the hot tub. The large living room, dining room and kitchen give plenty of space for any family or group.

4.96 out of 5 average rating, 234 reviews

Treehouse in Dorset

Raven's Roost- private luxury treehouse with sauna

Unplug your tech and let the sights and sounds of the forest be your muse. Treat your body to the healing powers of a eucalyptus sauna. Cool down in the outdoor shower, stargaze, crack a book, play some Scrabble, colour or write. Sing with the wolves, skate through the forest, canoe, climb, swim, ski or snowmobile from your door to the OFSC trail. The quaint town of Dorset is in the center of one if Canada's most impressive landscapes. Escape. Exhale.

4.91 out of 5 average rating, 352 reviews

Cabin in Tory Hill

The Nest on Irondale River in Geocaching Capital

The Nest is a one room cabin with a screened in porch. There is a queen bed with sheets, queen pillows and comforter. Relax by the river or take out a kayak and paddle upstream to the rapids. After a BBQ dinner, enjoy smores at the large campfire pit. Meander the trails throughout the property and just be. Everything is here for a simple but soul restoring getaway. There is no shower and the toilet is in an outhouse.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Head Lake holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Head Lake

5 out of 5 average rating, 66 reviews

Cabin in Lake of Bays

Cozy Waterfront Muskoka Cabin

SteveRating, 5 stars2 weeks ago

We had a really lovely stay - the cottage is spacious and tastefully appointed, and the location is perfect, with long sunsets over the water. Highly recommended base from which to explore the gorgeous Muskoka district, whether as an escape from Toronto or for out-of-towners.

4.8 out of 5 average rating, 44 reviews

Cabin in Kirkfield

Beautiful 3 Bedroom Cabin with a Sauna & Canoes

JennRating, 5 stars3 weeks ago

This cottage was our dream place for our small friend group’s getaway. The back patio and waterfront make the perfect setting. The interior is clean and spacious with full kitchen, living room and 3 bedrooms. Thank you for a perfect trip!

4.92 out of 5 average rating, 39 reviews

Cabin in Huntsville

Waterfront A-frame Retreat with Sauna & Hot tub

JasonRating, 5 stars2 weeks ago

We had a great stay at Lisa's place. Our family spent a lot of time on the water exploring the lake in the available canoe and kayaks and really enjoyed the sauna and hot tub in the evenings. The outdoor space is setup perfectly for living outside on those sunny days and inside the cabin is cozy and has all the amenities you need if the weather isn't great.

Cottage in Kawartha Lakes

4.88 out of 5 average rating, 52 reviews

Cozy 3bed-1Bath Cottage w/fire pit, pet friendly

AbhinavRating, 5 stars1 month ago

Amy & David's place is peaceful heaven, when you need quite break from your work and city. Its a good quiet neighbourhood with all necessary resources. Although everything nearby closes at 8pm can be challenging. So stock up your food in advance. Amy & David are friendly and responsive whenever needed. All the nearby attractions are just 15-20 mins away. The best part is star gazing at night. Pro tip: bring your tripod to get a breathtaking snap of sky full of stars. Thank you guys, it was a wonderful time.

5 out of 5 average rating, 66 reviews

Cabin in Haliburton

LakeKabin: Lakefront, HotTub, Arcade, Kayaks&SUP

MehrdadRating, 5 stars1 week ago

The cottage is very clean, cozy and full of things to do, the lake that it’s located on is spectacular. There are a bunch of ways to enjoy the water, kayaks, a canoe, paddle board and row boat. The hosts are very friendly and responsive we had a great time visiting their place

5 out of 5 average rating, 37 reviews

Cottage in Huntsville

Priolo on the Bay Moody Escape -Lake Sauna Hot Tub

BhanuRating, 5 stars3 weeks ago

We had the absolute pleasure of staying at Priolo on the Bay – Moody Escape, and it was nothing short of magical. From the moment we arrived, it was clear that Andy is a truly exceptional host. Every detail was thoughtfully curated to create a luxurious yet cozy escape. The cottage itself is immaculate – modern, stylish, and unbelievably comfortable. It strikes the perfect balance between high-end living and rustic charm. Tucked away in the heart of nature, it still offers every convenience imaginable: from fully stocked cutlery and snacks to campfire treats, firewood for both the sauna and outdoor firepit, a gas oven, extra lighters—you name it, it was there.The interiors are spotless and beautifully designed, making the entire space feel like a warm, peaceful retreat. Sitting by the fire, unwinding in the sauna, or just enjoying the serene forest surroundings—it all felt like a dream.This is the kind of place that makes you not want to leave!

4.84 out of 5 average rating, 61 reviews

Tiny home in Harcourt

Tiny Home Experience

BrookeRating, 5 stars2 weeks ago

My husband and I spent 4 nights at the tiny home on our honeymoon! The place was beautiful, private, and we LOVED the sauna and cold plunge amenity. One thing I will say is that the location is VERY remote, and you will be 25 minutes from the nearest store, gas station, or restaurant. So make sure to stock up on any supplies! We only had one roll of paper towels and one trash bag for our stay which was fine, but considering the remoteness, you’re definitely gonna need some more supplies than that! There is also a fork in the road where you must choose between two cabin names we weren’t aware of, but take the left road! While this place is very private because of the location, be prepared to be VERY exposed due to lack of any blinds or privacy curtains. At night with lights on, you can clearly see into the entire cabin and bathroom from outside, so that was quite an adjustment for us, especially sleeping. Overall we had so much fun at this cabin and would definitely return!