House holiday rentals in Highlands East

4.96 out of 5 average rating, 161 reviews

A spacious guest suite features a cozy seating area with a sectional sofa and a decorative rug. A large queen bed is positioned against the wall, accompanied by modern window treatments. A small table and chair add functionality, while recessed lighting brightens the room.

Home in Bancroft

2nd Floor Guest Suite

2nd floor guest suite located only 5 minutes to downtown Bancroft. This large suite has a queen bed, queen pull out sofa bed, mini fridge with freezer, microwave, smart tv, keurig machine (tea, coffee, sweeteners and creamers provided) and spacious bathroom with walk in shower. Please note that a full flight of stairs must be climbed to access this unit once inside the door. Please also note there is no kitchen in this suite, cooking appliances & candles are prohibited due to fire risk.

FamilyValueAccuracy

4.94 out of 5 average rating, 229 reviews

A modern two-storey home features a sleek design with large glass windows and balconies. The outdoor area includes a spacious deck with seating arrangements, while a decorative neon sign reads 'Water's Edge' against a textured green wall, enhancing the contemporary aesthetic.

Home in Belleville

Spectacular Waterfront Home in PEC

Situated on the edge of the beautiful Bay of Quinte, this brand new modern build is sure to steal your breath. Built in 2023, this stunning two-storey waterfront oasis, Water’s Edge, is located just over the Bay Bridge in spectacular Prince Edward County. Featuring two kayaks, fishing gear, outdoor propane fire table, and an upper and lower deck with front row seats to the most unforgettable sunsets. Water’s Edge is conveniently located to both Belleville and all that PEC has to offer.

LocationFamilyNearby

4.96 out of 5 average rating, 140 reviews

A cozy interior features warm wooden walls and ceiling, illuminated by natural light from the large window. A comfortable couch and wooden dining table are present. A wood stove is positioned beside the window, offering a snug atmosphere. A vibrant rug adds texture to the floor.

Home in Havelock

All Season Secluded Cabin Rental in the Woods

This secluded cabin in the woods is near Peterborough Ontario, about two hours from Toronto. Getaways offer a peaceful escape into nature. One queen and one twin bed up in the loft. The kitchen has a 2 burner counter top stove, fridge, toaster oven and kettle. Air Conditioning . Charcoal BBQ. No running water. .water jugs and bottled water are provided. .clean outhouse plus port-a-potty in loft Please bring your own sheets, pillow cases and towels No pets please.

LocationFamilyComfort

A bright and inviting living area features a yellow accent chair paired with a patterned throw pillow. A round area rug anchors the space, while a wooden side table and a glass-front cabinet add warmth. A large artwork adorns the wall opposite a dining area.

4.95 out of 5 average rating, 104 reviews

Design-Forward Luxury Retreat w/ Pool + Hot Tub

Welcome to Valley Road House — a secluded, design-forward retreat in complete privacy, surrounded by nature. Open living spaces and natural light create a calm, elevated feel. Enjoy a sleek chef’s kitchen, curated interiors, and games room. Outside, relax in a heated pool, spacious seating area, and 7-person hot tub. End your day by the firepit under open skies. With no neighbors in sight, this is a rare escape of space, stillness, and quiet luxury. Perfect for groups and families.

ValueFamilyView

4.97 out of 5 average rating, 156 reviews

The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.

Home in Barrie

Waterfront Home, City/Sunset View & Steps to Beach

Waterfront w/ private dock. Renovated upscale home + new hot tub, full city bay views w/summer sunsets+sunrise. Steps to Minet's Point beach & park. 4 proper bdrms & 2 pull out couches(Queen & Twin) 3 full bthrms + sauna, over 2400+sqft. Prking for 3 cars, additnal prking available via lot beside. Gas BBQ, fire pit, 2x gas FP, fast Wifi & 77" TV, wshr/dryr. 48amp EV pwr. Minutes to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

LocationFamilyIndoor spaces

4.88 out of 5 average rating, 215 reviews

Kennisis Lake Luxury | Lakefront Retreat & Hot Tub

Escape to modern luxury on Kennisis Lake! 🌊 Enjoy a private water front with rare shallow entry. Unwind in the premium 7x7’ hot tub under the stars. ✨ The designer interior features a chef's kitchen w/ dishwasher, AC, full laundry, and High-Speed Wi-Fi—perfect for remote work. 🚣 Included: 3 kayaks, Gas BBQ, and lakeside fire pit. Easy year-round access on paved roads. A high-end retreat for families/couples. Book your 2026 summer getaway now! 🌲

ValueFamilyCheckout

Home in Monteagle, Ontario.

A spacious bedroom features a large bed with soft bedding and decorative pillows. A colorful floral artwork adorns the wall above the bed, while large windows provide a serene view of the snowy landscape outside.

4.97 out of 5 average rating, 186 reviews

Rose Door Cottage

Quaint and cozy 1 bedroom cottage tucked along the southeastern shore of a small, quiet lake. Recently renovated, the cottage is the perfect romantic getaway. It's located 1 km from snowmobile/ATV trails, 15 minutes from Bancroft and 45 minutes from Algonquin Park. The cottage includes a floating dock with swim ladder, bbq, woodburning outdoor firepit, canoe, kayaks, woodburning indoor fireplace, smart tv with starlink satellite.

FamilyValueSolo travel

The charming exterior of a converted church is presented, showcasing a striking red brick facade and a steeply pitched roof. Tall trees and lush greenery surround the building, adding to the serene setting. A welcoming entrance with a dark door and steps leads to the front.

4.97 out of 5 average rating, 309 reviews

The Prince Edward County Church, A Unique Escape

Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.

LocationValueRiver

4.97 out of 5 average rating, 143 reviews

A modern cabin is nestled among tall trees, showcasing large floor-to-ceiling windows that invite natural light. A spacious covered porch, framed by lush greenery, features outdoor seating. The grassy area surrounding the cabin adds to the serene atmosphere of the wooded retreat.

Home in Eagle Lake

HyggeHaus—sleek snuggly secluded apres-ski cabin

For a getaway that merges serenity with style; imagination with intention, look no further than HyggeHaus and its private Haliburton Highlands wooded retreat. Indulge in a stay where there is time and space for both leisure and adventure, and where beautiful design enables beautiful experiences. To view a short property video, search Youtube for "HyggeHaus Eagle Lake Haliburton". STR Licence# STR-26-00031

LocationFamilyBackyard

4.98 out of 5 average rating, 237 reviews

An exterior view of a modern black tiny house is depicted, surrounded by trees and natural foliage. Two sets of stairs lead to the entrance, with a gravel pathway visible. Window placements create a unique design, and soft lighting illuminates the scene against the evening sky.

Home in Gravenhurst

Woodland Muskoka Tiny House

**BOOK 7 NIGHTS, PAY FOR 5 (28% OFF)** Enjoy the sounds of nature when you stay in this unique tiny house. This 600 sq ft home is nestled amongst 10 acres of towering trees, granite rock and trails to explore. The tiny home will not feel so tiny once inside. With high ceilings, plenty of windows, and surprisingly spacious rooms - it is the perfect hideaway for those wanting to unplug in Muskoka.

ValueLocationAccuracy

4.95 out of 5 average rating, 136 reviews

The custom-built A Frame cabin is set amidst lush greenery, featuring a striking black exterior and a distinctive peaked roof. A spacious deck extends at the front, furnished with seating, and surrounded by nature for a serene environment.

Home in Bracebridge

Secluded Muskoka A-Frame | Hot Tub, Dock, Firepit

Escape to a private, custom-built A-Frame on 3 acres in the heart of Muskoka—complete with your own dock on a quiet stretch of the Muskoka River. Unwind in the hot tub, paddle the river, or relax by the fire under the stars. ★ Guest favourite with 4.9★ rating ★ One of the few stays in the area with a private hot tub + river access *Please note-all guests must have a minimum of two reviews to book*

ValueLocationHiking

4.96 out of 5 average rating, 168 reviews

The exterior of the A-frame home is showcased, featuring a striking black facade and tall triangular roof. Large windows illuminate the interior, and a spacious wooden deck extends across the front, surrounded by lush greenery that encapsulates the natural setting.

Home in Georgian Bay

A-Frame Hidden in the Forest Muskoka, Georgian Bay

Welcome to our A-frame /Triangle House, Wifi, Sauna, Kitchen, A/C, Free Parking, King Bed, FIFA friendly, Smart Tv, Peaceful, Social Media Favourite, Top Choice for city escape, and an ideal weekend getaway. Come heal, enjoy the light luxury in nature, and enjoy the slow living at this premium vacation experience. Rare architecture, designer cabin. Come and gather energy in this forest sanctuary.

ValueLocationQuiet

Popular amenities for Highlands East house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 61 reviews

A serene backyard view showcases a well-maintained lawn bordered by diverse greenery and a calm river. Several seating areas, including white chairs and a shaded gazebo, provide relaxation spots. A swimming pool is visible, reflecting the clear blue sky above, creating a peaceful outdoor setting.

Home in East Gwillimbury

Private river access with pool, canoes, kayak

FamilyLocationRiver

4.8 out of 5 average rating, 125 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Horseshoe Valley

King Bed, Pool, Gym, Ravine View, Your Getaway!

ValueFamilyHot tub

4.9 out of 5 average rating, 139 reviews

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

ValueFamilyTV

4.94 out of 5 average rating, 247 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

LocationFamilyAccess

4.94 out of 5 average rating, 207 reviews

Dragonfield House: a beautiful stay in central PEC

ValueFamilyDecor

4.89 out of 5 average rating, 84 reviews

A hot tub is positioned on a wooden deck, offering a view of expansive greenery and Rice Lake in the background. Lush greenery and blooming white flowers frame the scene, and the sky above is clear with soft clouds, enhancing the serene outdoor setting.

Home in Gores Landing

Oriole Ridge Retreat, Hot Tub, King Suite

ValueFamilyCondition

The exterior of a spacious home is showcased, featuring a well-maintained lawn and a gravel driveway. Large windows provide natural light, and the above-ground pool is visible nearby, surrounded by greenery. A sunset sky adds a warm ambiance to the setting.

4.86 out of 5 average rating, 103 reviews

Welcome to The Fairview! Arcade, Hot tub, and Pool

LocationValueOutdoor spaces

4.86 out of 5 average rating, 108 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

ValueLocationHospitality

Weekly house rentals

4.98 out of 5 average rating, 100 reviews

The exterior of the cottage is presented, featuring a large deck with ample outdoor seating. Below, a fire pit area surrounded by red chairs is visible, along with stone pathways leading through the lush greenery. Large windows reflect the natural surroundings.

Home in Barry's Bay

LUX Lakefront: 6 Bedrooms, 12 Guests, w/Hot Tub

FamilyLocationLayout

4.97 out of 5 average rating, 151 reviews

Home in Trent Lakes

Luxury 5000sqft+ Waterfront Cottage: Sauna Hot Tub

LocationFamilyWalkability

4.97 out of 5 average rating, 245 reviews

An A-frame house is presented with a blue exterior amidst a snowy landscape. The structure showcases a sloped roof with multiple windows and a door leading to a deck. Surrounding trees, partially covered in snow, create a serene and natural setting.

Home in HUNT

Modern & Charming Eh-Frame | 4-Season Chalet

ValueLocationWalkability

4.88 out of 5 average rating, 17 reviews

Designer A-Frame | Percy Lake + Cube Sauna

FamilyLocationView

Home in Algonquin Highlands

4.91 out of 5 average rating, 256 reviews

Stunning Lakefront Retreat: Sauna, Hot Tub, EV Chg

ValueFamilyHeating

4.89 out of 5 average rating, 140 reviews

A serene lakeside deck features wooden planks and blue lounge chairs, providing a comfortable space for relaxation. A long dock extends over the calm water, surrounded by greenery, offering an ideal spot for swimming and enjoying the natural scenery.

Home in Eagle Lake

Lively Lakehouse with hot tub

LocationValueGetting around

5 out of 5 average rating, 63 reviews

NEW Aframe w/ sauna, outdoor shower & 2km to town

LocationFamilyQuiet

4.87 out of 5 average rating, 262 reviews

An aerial view captures a two-story cabin surrounded by vibrant autumn foliage. The landscape is adorned with various shades of orange, yellow, and green, showcasing the natural beauty of the wooded area. The winding path leading to the cabin is lined with scattered rocks and red outdoor chairs.

Home in Bobcaygeon

52 Acre Luxury Cabin - Hot Tub, Firepit & Trails

FamilyLocationBathroom

Private house rentals

4.96 out of 5 average rating, 49 reviews

The image captures a private lakeside setting during sunrise. Adirondack chairs surround a fire bowl on a circular stone area. A private dock extends into the calm lake, reflecting the soft hues of morning light. Lush greenery frames the scene, enhancing the tranquility.

Home in Kawartha Lakes

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

LocationFamilyKitchen

5 out of 5 average rating, 25 reviews

Home in Huntsville

Muskoka Waterfront Cottage | Canoes, FirePit & BBQ

LocationFamilyCheckout

4.95 out of 5 average rating, 93 reviews

The exterior view showcases a two-level cottage nestled among trees. A spacious wooden deck is emphasized, featuring a large dining table and comfortable seating. A staircase leads from the deck to the yard, where a landscaped area invites relaxation and connection with nature.

Home in Wilberforce

Lakeside getaway with hot tub

LocationFamilyAccuracy

5 out of 5 average rating, 3 reviews

Home in Fenelon Falls

Cedar Barrel Lakehouse - Hot Tub|Water Toys|Views

LocationFamilyCleanliness

A modern retreat is nestled among lush greenery, featuring expansive glass windows that invite natural light into the living spaces. The structure's sleek lines and natural stone accents contrast beautifully with the surrounding forest. A gently sloping landscape leads to the entrance.

5 out of 5 average rating, 22 reviews

Luxury Lakefront Retreat | Haliburton

FamilyLocationView

5 out of 5 average rating, 25 reviews

Home in Kawartha Lakes

Stonegate Retreat | Sauna, Fire Pit, Lake Access

LocationFamilyNearby

4.9 out of 5 average rating, 30 reviews

Home in Burk's Falls

Luxe Lakehouse Retreat with Sauna

LocationValueSleep quality