Holiday rentals in Highland

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Top-rated holiday rentals in Highland

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Top guest favourite
An open kitchen and living area are presented, featuring a large kitchen island with seating. Modern appliances, including a refrigerator and stove, complement the sleek cabinetry. A cozy sofa area is seen in the foreground, providing a view into this well-lit and spacious design.
Home in Milford Charter Township
4.97 out of 5 average rating, 185 reviews

Downtown Milford 1 BR Flat

Enjoy a special experience in your luxury, private one bedroom flat, located in charming downtown Milford. While apart of a triplex, you will have your very own flat that includes everything you will need to have an outstanding stay. This recently remodeled flat includes an open floor plan with a well equipped kitchen, inviting living room, spacious bedroom with a queen size bed and even an over-sized desk so that you can "work from home", and a "to die" for bathroom. Two blocks from Mainstreet.

Guest favourite
The exterior of the A-frame house is framed by lush trees, featuring a welcoming front porch and a distinct triangular roof. Inside, a spacious living area showcases large, open spaces with comfortable seating and a lofted balcony that overlooks the lower level, offering a bright and airy atmosphere.
Home in White Lake charter Township
4.95 out of 5 average rating, 237 reviews

MOD Mid Century 1964 A-frame with game room

1964 Mid Century A-Frame - romantic getaway. Short walk to lake, large wooded lot, outdoor fire pit, dining, BBQ grill, hot tub & bikes. Large bathroom w/ jacuzzi tub, open floor plan w/ large kitchen & living area w/ electric fireplace. Two upstairs bedrooms. Master has queen sized bed, work space & balcony. Front bedroom w/2 futons & overlooks the living room. Basement game room w/ sauna, pool table, foosball, shuffleboard, Jenga & laundry. Close to shopping, golf, ski resort, cider mill.

Guest favourite
A well-maintained single-story home is set on a grassy lawn, framed by trees and bushes. The structure features a symmetrical design with large windows reflecting natural light. A clear blue sky completes the serene outdoor scene, enhancing the home's inviting presence.
Home in Milford Charter Township
4.95 out of 5 average rating, 369 reviews

Luxury Home - Indoor Pool - Fabulous Location

Our neighbors love that we DO NOT ALLOW parties & LATE NIGHT, AFTER 9pm outdoor activities. We are required to limit the total number of individuals at our home to no more than 10 at any time, including visitors. Include visitors in guest count. At the end of a quiet cul-de-sac on 2 acres. When we are not using our 2nd home, it is available for Airbnb guests. Our family home since 1986; when I designed & personally built it for my parents. Fully renovation in 2018, with continual updates.

Top guest favourite
A bright dining area features a wooden table surrounded by chairs, positioned beside a large bay window. On the opposite side, a modern kitchen is showcased with sleek cabinetry and bar seating at the island, illuminated by pendant lights.
Home in Plymouth
4.97 out of 5 average rating, 195 reviews

Charming Plymouth retreat • hot tub • fire pit

Welcome to our 1913 modern yet charming 3 bed (2 ensuite), 2-full bathroom home nestled just a short stroll away from the heart of downtown Plymouth. With a walk score of 75, this is an unbeatable location with an array of amenities. Enjoy this perfect retreat for your next getaway. 3 mins → DT Plymouth 19 mins → Detroit Metropolitan Wayne County Airport ✈ 20 mins → Ann Arbor Retreat w/ hot tub, hammocks, game & entertainment rooms, fire pit, washer/dryer, gated yard, cozy family home!

Guest favourite
A serene lakeside view is captured, showcasing gentle ripples on the water's surface under a soft sky. A rainbow arches gracefully above the horizon, with lush trees framing the scene and enhancing the tranquil ambiance.
Guest suite in Brighton
4.84 out of 5 average rating, 472 reviews

Lakeside Hilltop

Private 2-bedroom hilltop apartment overlooking two lakes, less than a mile to both I96 and US23, and 20 minutes to downtown Ann Arbor, 30 minutes to Lansing, 15 minutes to Novi, Farmington, Livonia, Northville, Plymouth and 45 minutes to downtown Detroit! Bring your canoe, kayak, bike, boards/skis, golf clubs, hiking gear for a vacation away that is still close by. Within minutes of downtown Brighton, Kensington Metro Park, Island Lake Recreation Area, Brighton Rec Trails and Mt Brighton.

Guest favourite
The living area features a spacious sectional sofa centered around a coffee table. Artwork adorns the walls, and natural light floods in through a large window, illuminating the room. A lamp stands nearby, and a dark patterned rug adds contrast to the floor.
Apartment in Milford Charter Township
4.94 out of 5 average rating, 127 reviews

Rivers Edge Condo in Downtown Milford

Cozy, stylish two bedroom condo in the heart of the Village of Milford. Milford is a safe, vibrate, and fun neighborhood, with many restaurants, bars, breweries, and within walking distance. You can stop by the coffee shop, bakery, or raw juice bar in the morning as you walk through town. Later, enjoy shopping- or go for a hike or kayak at one of several beautiful parks nearby! This is an excellent spot for people looking for a fully furnished short-term rental with modern characteristics

Top guest favourite
Two blue Adirondack chairs are positioned on a green lawn overlooking the calm surface of the river. A fire pit is situated nearby, and a wooden dock extends into the water. Lush trees and colorful flowering plants line the opposite bank, reflecting a serene atmosphere.
Home in Milford Charter Township
4.99 out of 5 average rating, 67 reviews

River Retreat West

Unique home on the bank of the Huron River, a half-mile walk to the pedestrian-friendly Village of Milford, known for its array of shops, restaurants, outside dining, concerts, and festivals. Dine or relax on one of two decks overlooking the river. You’ll see abundant wildlife depending on the season. There’s a fire pit at river's edge for relaxing or roasting marshmallows, and a gas grill on the dining deck. Four sit-in kayaks available May 15–Oct. 15, more for rent nearby.

Top guest favourite
The exterior of the cottage is surrounded by lush greenery, featuring a small patio with a table and chairs under an umbrella. Two kayaks are resting on the grass nearby, and a gentle slope leads to the entrance of the cottage.
Cottage in Milford Charter Township
4.95 out of 5 average rating, 160 reviews

Caroline Cottage

Unique one-room cottage on the bank of the Huron River. A half-mile walk to the pedestrian-friendly Village of Milford, known for its array of shops, restaurants, outside dining, concerts, and festivals. Perfect bungalow for single, couple, or small family. Living area has double sofa bed. Tiny home with many unique features. Fire pit at river's edge for relaxing or roasting marshmallows, and a gas grill on the dining patio. Two sit-in kayaks available May 15–Oct. 15.

Top guest favourite
The cottage is illuminated by soft outdoor lights, casting a warm glow across the yard. Reflections shimmer in the calm lake water, creating a serene atmosphere. The surrounding trees provide a natural frame, enhancing the peaceful setting at night.
Island in Springfield Township
5 out of 5 average rating, 32 reviews

Serene Island getaway for 2 in Clarkston Michigan

Island Living! This peaceful cottage is on an island, we will take you there by boat & drop you off, it’s a short ride. You have access to kayaks & paddle pontoon to come and go. Queen bed 1.5 baths. Full kitchen area. Decks all the way around. Watch the sunrise from the back deck & the sunset from the front deck. Bonfire wood is included as well. Parking for one vehicle. A quiet & romantic getaway for 2. Downtown Clarkston & Renaissance Festival both close to island.

Top guest favourite
An aerial view showcases a serene lake surrounded by lush greenery and forested areas. The water reflects the sky, creating a peaceful atmosphere. The expansive landscape reveals meadows and trails, highlighting the natural beauty of the environment.
Guest suite in Hartland
4.93 out of 5 average rating, 71 reviews

Entire Lower Level walkout on Private lake.

Great Retreat. Private nonmotor Dunham Lake. Two level 4500 Square Foot home on 2 acre lot. Private entrance lower level 2000 square feet guest suite is yours. Living area w Great Room, Kitchen, full size refrigerator, cooktop and microwave. Barbeque. Firepit. Pool Table. Large Screen TV. Fireplace. Sauna. Separate Furnace/AC for your convenience. Walkout to 32 acres of woods/trails, sandy beaches, park area. Looking forward to providing a wonderful retreat.

Top guest favourite
A cozy bedroom features a spacious bed dressed in red and white linens, positioned beside a framed piece of floral artwork. A flat-screen television is mounted above a wooden fireplace, which is complemented by lanterns and decorative items on a nearby shelf.
Guest suite in Springfield Township
4.96 out of 5 average rating, 449 reviews

Cozy Apartment in our Log Home.

Trim Pines is the perfect small space for a quiet stay and is enjoyed by guests in every season. Our lower one room walk-out is comfortable for 1 to 2 people for short or long term stays. It is a great place to unwind and relax. This tranquility is located 8 miles from I-75 in Davisburg, Michigan. Our guests enjoy local festivals and concerts at Pine Knob Music Theater, golf at nearby courses and biking and hiking at local County, Metro and State Parks.

Top guest favourite
A spacious living area features two couches in neutral tones, arranged around a low coffee table. Natural light filters through large windows, with sheer curtains adding softness. A dining area with a small table and chairs is visible in the background, leading to a modern kitchen.
Flat in Holly
4.96 out of 5 average rating, 74 reviews

Boxcar Bunker - Downtown living at its finest.

The Boxcar Bunker will delight and refresh your senses with the fully updated interior and appliances. Take a walk to downtown Holly and enjoy the many shops and restaurants along with multiple festivals and events happening all year round! This unit is universally designed to accommodate everyone including those with mobility issues and wheelchairs. All essentials are at your fingertips to provide an effortless and worry free stay here in Holly, MI.

Popular amenities for Highland holiday rentals

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  2. United States
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  4. Oakland County
  5. Highland