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Holiday rentals in Hillsdale

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Quick stats about holiday rentals in Hillsdale

  • Total holiday rentals

    Explore 40 holiday rentals in Hillsdale

  • Nightly prices starting at

    Hillsdale holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 3,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Hillsdale holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Hillsdale rentals

  • 4.9 Average rating

    Hillsdale stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Hillsdale

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

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Guest favourite
Home in Hillsdale
4.96 out of 5 average rating, 57 reviews

Hillsdale Cottage | Whole House

This recently renovated home offers the perfect blend of historic charm and modern comfort, with original architecture, cozy interiors, and a welcoming porch. Ideal for both short- and long-term stays, with a fully stocked kitchen and four comfortable beds. Walking distance from Hillsdale College and directly across from Handmade sandwich shop. Exclusively 100% cotton sheets and non-toxic cleaning products are used! (Be sure to specify the accurate # guests when booking a stay at the Cottage!)

Guest favourite
A stainless steel mug featuring the words 'Bear Lake' with a bear silhouette stands on a wooden dock. In the background, a clear blue sky is visible, along with boats anchored on the shimmering lake. Lush greenery borders the water's edge.
Cottage in Hillsdale
4.94 out of 5 average rating, 86 reviews

Bear Lake access/Getaway/family friendly-Bears Den

Bear Lake welcomes you. Relax with friends/family at this peaceful and sometimes spirited getaway steps away from ALL SPORT Bear Lake. Shared dock where you can swim, Kayak, fish, or merely float. A Public access launch is just yards away for personal watercraft. Evenings sprinkle the sky with plenty of stars to gaze at. Fishing, boating, kayaking, or just relaxing are all at your finger tips. Golfing, restaurants, shopping, and walking/ biking trails nearby. Pontoon/Kayak rentals available.

Guest favourite
A living room area features a stone fireplace, which is complemented by a wooden mantel displaying a clock and a decorative item. Sunlight streams in, highlighting a nearby bookshelf and a vintage wooden cabinet, creating an inviting scene.
Home in Hillsdale
5 out of 5 average rating, 10 reviews

The Lake Cottage

Welcome to your perfect getaway. This quiet and comfortable, two bedroom home offers the ideal balance of relaxation and adventure. The Lake Cottage is located right on Lake Baw Beese and is perfect for families, couples, or friends looking to unwind and explore Hillsdale, Michigan. Whether you’re here to kayak, grill, or just enjoy a mug of coffee and breathe in the fresh air from one of our porches, this home is your base for a peaceful and beautiful day. 3.4 miles from Hillsdale College.

Top guest favourite
A hot tub is positioned under a wooden pergola, surrounded by lush greenery. The lake reflects a colorful sunset sky, and a well-maintained outdoor area features seating and a shed, creating a serene space for relaxation and enjoyment.
Home in Hillsdale
4.96 out of 5 average rating, 112 reviews

Sapphire Shores: Lakefront W/Hot Tub & Fireplace

Welcome to Sapphire Springs, your lakefront retreat on South Sand Lake, MI! Perfect for all seasons, this home offers endless fun indoors and out. Outside, enjoy a sandy beach, kayaks, paddleboards, a grill, fire pit, hot tub, and outdoor games. Indoors, unwind in the game room with a pool table, arcade games, and TV. Relax in the living room, spin some vinyl on the turntable, and cook up a feast in the fully equipped kitchen. The coffee station has an espresso machine, drip, and Chemex.

Top guest favourite
The exterior of Frogmore Cottage features a welcoming deck with handmade Adirondack chairs overlooking the surrounding greenery. Bright kayaks are stacked beside the cottage, ready for use. The driveway runs alongside, providing parking access. A neatly landscaped area enhances the cottage's inviting exterior.
Cottage in Hillsdale
4.98 out of 5 average rating, 50 reviews

The Frogmore on Baw Beese Lake!

Welcome to Frogmore Cottage, located on the shoreline of Baw Beese Lake! Newly renovated and stocked with all you'll need, Frogmore is a clean, cozy, bright and airy, two bedroom, one bathroom, 550 square foot cottage. Frogmore is just two miles from downtown Hillsdale and three miles from Hillsdale College. Relax on the deck that overlooks the lake and enjoy the kayaks to explore the shoreline of the largest lake in Hillsdale County!

Guest favourite
A serene lakeside scene is depicted at dusk, featuring silhouetted trees against a colorful sky. Four white Adirondack chairs are positioned neatly near the water's edge, inviting a moment of relaxation as vibrant hues reflect on the lake's surface.
Flat in Hillsdale
4.9 out of 5 average rating, 154 reviews

Come Stay At The Lake!

Enjoy your stay in this very private apartment on beautiful, Baw Beese Lake. If you are seeking a quiet stay where you can sit, relax and read a book at the water's edge, then look no further. There is parking for most any size vehicle from economy size to motor homes. This is a fully furnished apartment with kitchenette. This second story apartment is within 1 mile of downtown Hillsdale and within 2 miles of Hillsdale College.

Guest favourite
Cabin in Osseo
5 out of 5 average rating, 11 reviews

Cowboy's Wolf Den

This unique little hand crafted canin is close to everything, making it easy to plan your visit. This is a rustic primitive cabin with a full size bed This cabin Sits in our Rustic hand crafted Cowboy Town 🐎 complete with horses, pond for fishing or paddling around, river for exploring, lots of hiking and horse trails, close to bathroom and outdoor shower along with the kitchen area lots of wildlife and wilderness to enjoy

Top guest favourite
A historic home is framed by vibrant autumn trees, showcasing hues of red, orange, and yellow. A wide front porch invites relaxation, and an American flag adds a touch of character. The surrounding walkways are lined with fallen leaves, creating a welcoming outdoor space.
Home in Hillsdale
5 out of 5 average rating, 26 reviews

The Hillsdale Haven

Welcome to Hillsdale Haven, a beautiful historic home located along one of the nicest streets of downtown Hillsdale, Michigan. This cozy, three bedroom, two bathroom home is 2 blocks from Hillsdale Hospital, 4 blocks from the commercial district, and a short drive (1 mile) from Hillsdale College. Loaded with charm, the Hillsdale Haven has everything you need for a restful stay in Hillsdale, Michigan.

Top guest favourite
A modern, single-story home is depicted, featuring a combination of red and gray siding. The structure includes large windows and a welcoming entrance with a sign that reads 'Proctor House.' A landscaped area with stone retaining walls and a grassy lawn is visible in the foreground.
Home in Hillsdale
4.89 out of 5 average rating, 292 reviews

Comfy home in recreational town

We renovated the house with a modern kitchen, laundry room, new bathroom with spacious shower, new bedrooms with plenty of closet space, secure parking and new sidewalks. Close to historic weekly country market, Hillsdale College, bike trail, lakes in historic town. The North Country Trail and the Baw Beese Trail are closeby, as is Baw Beese Lake, Lost Nation State Game Area and the St. Joe River.

Top guest favourite
A well-equipped kitchen is observed with modern appliances and ample counter space. Open shelving displays colorful dishware above a stainless steel sink, while a bowl of fruit is placed on the countertop. Natural light pours in through the windows, illuminating the space.
Home in Hillsdale
5 out of 5 average rating, 24 reviews

The Farmhouse

Retreat to the timeless elegance of this newly renovated 1908 home. Complete with 3 bedrooms, 2 full bathrooms, a cozy living area with a flat screen TV, and a spacious, farm-style kitchen, this Michigan vacation rental is a short walk to Hillsdale’s charming downtown. ‼️The third floor of this home contains another queen bed and two twins. It can be booked for an additional fee.

Guest favourite
The exterior of a charming white house is framed by vibrant autumn foliage. A mix of orange and red leaves from nearby trees can be seen, along with a green lawn and a white picket fence in the background. An American flag is visible, adding to the inviting atmosphere.
Home in Jonesville
4.95 out of 5 average rating, 120 reviews

The Garden House

Relax with the whole family in this charming old home, with swings on the front porch and an overgrown English cottage garden in back. Less than ten minutes from Hillsdale College with a fully equipped kitchen, this makes a great home base for college families. When we travel, we enjoy places with character, and we have maintained the character of this old fashioned family home.

Top guest favourite
Home in Hillsdale
4.99 out of 5 average rating, 77 reviews

Hillsdale’s Hidden Condo Hideaway

This is a newly built, luxurious condo with 3 bedrooms and 2 bathrooms featuring cathedral ceilings, a large kitchen island, and gorgeous master bathroom. It is located in a quiet, rural neighborhood. If you enjoy the outdoors, there is a paved walking path to Baw Beese Lake. This home is 2 miles from Hillsdale College and just minutes from downtown Hillsdale.

Popular amenities for Hillsdale holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Hillsdale

Superhost
A well-maintained home is featured, showcasing a welcoming front porch with white railings and an American flag. Lush greenery surrounds the entrance, and a pathway leads to a stone-lined garden. The exterior reflects a traditional aesthetic against a clear blue sky.
Home in Hillsdale
4.68 out of 5 average rating, 34 reviews

Private home near Hillsdale Hospital

Guest favourite
A spacious bedroom is highlighted by a large iron bed adorned with a blue and white patterned bedspread. Soft lighting comes from two bedside lamps. A colorful area rug with floral designs complements the serene blue walls, and a doorway leads to an adjoining bathroom.
Home in Hillsdale
5 out of 5 average rating, 6 reviews

A Place of Rest

Guest favourite
A charming cabin is positioned amidst lush greenery, featuring a prominent stone chimney. A paved walkway leads to the inviting entrance, framed by well-maintained lawns and tall trees under a clear blue sky.
Home in Hillsdale
4.93 out of 5 average rating, 30 reviews

Cozy Cottage Near Campus

Superhost
A charming one-level cottage is positioned near Bear Lake, featuring a large concrete patio with patio furniture. A sandy area leads to the water, showcasing a private dock. The landscape includes green trees and grassy areas, contributing to a serene environment.
Home in Hillsdale
4.74 out of 5 average rating, 320 reviews

Bear Lake Cottage ... Pontoon Available for Rent

Top guest favourite
A sunlit sunroom features multiple glass sliding doors that offer views of the lake and surrounding greenery. Four cozy, woven chairs are arranged around two small, round wicker tables, creating a relaxing space. Natural light fills the area, enhancing the serene atmosphere.
Home in Hillsdale
5 out of 5 average rating, 34 reviews

Lovely 6Bed 4Bath Lakefront home with Game Garage

Top guest favourite
The exterior of a single-story home features large, dark-framed windows and a decorative arched window above the entrance. A well-maintained lawn is surrounded by trees, providing a serene backdrop. A small bush is planted near the front door.
Flat in Hillsdale
5 out of 5 average rating, 36 reviews

wildlife sanctuary 3 bed 2 bath Townhouse

Top guest favourite
The exterior of the lake cottage features a light-colored facade and a well-maintained front yard with decorative bushes. A screened porch extends across the front with large windows, allowing for natural light. A gravel pathway leads to the entrance, bordered by a low railing.
Guest house in Reading
5 out of 5 average rating, 7 reviews

Relaxation Party of 2

Guest favourite
A charming two-story home is framed by leafy trees and greenery. The exterior features light-colored siding, dark shutters, and a front porch with steps leading to the entrance. A well-maintained yard displays shrubbery and seasonal flowers, enhancing the inviting appearance of the property.
Home in Hillsdale
4.93 out of 5 average rating, 57 reviews

The Homestead at Hillsdale (.4 miles from campus)

When is the best time to visit Hillsdale?

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Frequently Asked Questions

  • What are the best places to stay in Hillsdale?

    Many visitors choose to stay near Hillsdale’s historic downtown, which has walkable streets and local shops. Around local lakes and near the college, vacation rentals are frequently suggested for scenic views and convenient access to activities.

  • What are the best things to do in Hillsdale with kids?

    Families often explore local parks, enjoy playgrounds, or visit nearby lakes for fishing and boating. Community events, seasonal festivals, and small museums are also popular for children.

  • What are some of the best things to do in Hillsdale?

    Explore the historic downtown, relax at local parks, or spend time on the water at one of the area’s lakes. Community events, small galleries, and neighborhood eateries add to the city’s inviting atmosphere.

  • How is the weather in Hillsdale?

    Hillsdale has cold winters around 20–39°F (-7–4°C) with occasional snow, while spring and fall stay mild. Summers are warm, averaging 64–87°F (18–30°C), and tend to be sunnier and more humid with occasional rain.

  • When is the best time to visit Hillsdale?

    Late spring through early fall is often recommended, as Hillsdale has comfortable daytime temperatures near 60–83°F (16–28°C) and many outdoor activities. Seasonal events and changing foliage also make autumn a popular time to visit.

  • What are the best places to visit in Hillsdale?

    The downtown district is often recommended for its historic buildings, galleries, and shops. Lakes in the area and college gardens draw visitors interested in outdoor activities and campus traditions.

  • What are some hiking trails in Hillsdale?

    Hillsdale has nature preserves and local parks with walking and hiking trails, suitable for different activity levels. Trails often wind through wooded areas, lakeshores, and open fields, providing a chance to explore local scenery.

  • What are some family activities we can do in Hillsdale?

    Hillsdale has family-friendly activities like exploring public parks, attending outdoor concerts, or participating in community events. Lakeside picnics and visits to small museums also create engaging experiences for all ages.

  • What are some of the best day trip ideas from Hillsdale?

    Day trips from Hillsdale often include exploring neighboring lakes, nature reserves, or small towns known for antique shops and local markets. Outdoor recreation, historic sites, and seasonal fairs in the surrounding region are frequently suggested.

  • Are there any pet friendly accommodations available in Hillsdale?

    Hillsdale has a variety of pet friendly accommodation options, including vacation rentals and private homes where pets are welcome. Many hosts in the area provide outdoor spaces or nearby parks, making it simple to bring your pet along.

  • What are some local tips for visiting Hillsdale?

    Locals suggest checking the community calendar for events, exploring the downtown shops and cafes, and enjoying early mornings at nearby lakes. Seasonal markets are also a favorite for sampling fresh produce and connecting with residents.

  • What is Hillsdale known for?

    Hillsdale is known for its locally rooted college campus, vibrant small-town traditions, and historic downtown area. The city has a blend of lake recreation, agricultural heritage, and annual community events.

  • What are the best hidden gems to explore in Hillsdale?

    Locals appreciate quieter park trails, family-run bakeries, and small art exhibits tucked into the downtown area. Markets and nearby nature preserves also provide a glimpse into the community’s slower pace and distinct charm.

  • What are the best foods to try in Hillsdale?

    Local diners and cafes in Hillsdale serve Midwestern comfort foods, including handmade pies and hearty breakfasts. Farm-to-table flavors and seasonal produce, especially during summer and fall harvests, are frequently suggested.

  • What should I bring for a trip to Hillsdale?

    Pack layers for weather shifts, comfortable walking shoes for exploring parks or downtown, and a rain jacket for spring or fall visits. In summer, sun protection is helpful, while winter calls for warm coats and gloves.

  • What is the nightlife in Hillsdale like?

    Hillsdale has a relaxed nightlife scene, with neighborhood pubs, casual restaurants, and local bars often hosting live music or trivia nights. Evenings are generally low-key, reflecting the community-oriented atmosphere.

  • What are the most popular events or festivals in Hillsdale?

    Hillsdale has annual fairs, seasonal festivals around Labor Day weekend, and traditions linked to the college calendar. Community parades, holiday celebrations, and farmers markets are frequently suggested throughout the year.

  • Are there family friendly vacation rentals in Hillsdale?

    Hillsdale has a selection of family friendly vacation rentals, including entire homes and cottages with multiple bedrooms and shared living spaces. Many are located near parks or lakes, making it easy to spend time outdoors together.

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