Vacation rentals in Hillsdale

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Top-rated vacation rentals in Hillsdale

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

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Top guest favorite
Cabin in Pittsford
5 out of 5 average rating, 25 reviews

Lost Nations Cowboy Town Mining Company Cabin

The whole group will be comfortable in this unique space. This cabin is hand crafted with old time decor, Sits in the one of a kind Cowboy Town close to the kitchen for cooking flushing bathroom and shower. Cabin has electric with ceiling fan, small fridge, coffee pot, pull out double bed and a single bed, two tables and chairs and a small couch, deck for sitting deck lights with fire ring, over looking the Cowboy town old cedar bridge horse pasture, pond for fishing trails, camping in a cabin

Guest favorite
The open floor plan showcases a spacious dining area with a circular table surrounded by upholstered chairs. Natural light enters through multiple windows, illuminating the living space with a sectional sofa and a lamp. A staircase leads to the loft area, where four twin beds are visible.
Home in Homer
4.97 out of 5 average rating, 136 reviews

Benham Schoolhouse

Take a quiet vacation at this fully renovated historical schoolhouse built in the 1800's. It offers an open floorplan with a loft area where the four twin beds are located *can be made more private by closing the barn doors. There is two full bathrooms, a large kitchen area, living space, dining space, and an open area we can set up to be used for craft activities or other activities upon request. It also has a Halo air purification system, stopping virus particles to travel through the HVAC.

Top guest favorite
Home in Hillsdale
4.96 out of 5 average rating, 106 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 favorite
Bungalow in Jackson
4.95 out of 5 average rating, 428 reviews

Barn Quilt Bungalow

The Barn Quilt Bungalow- Views of horses right out your window! Includes 1 bedroom (queen), 1 pull out mattress (queen), 1 bathroom (shower), living room, kitchen, heat & A/C. Walk the trails or walk to the winery. MAX OCCUPANCY is TWO guests. You can add a third for $30/night. Guests may not bring additional people, no matter how long. Airbnb will be contacted immediately if you exceed the max occupancy. No children, animals, or service animals (allergy/ health hazard).

Top guest favorite
The kitchen features black cabinetry and a stainless steel refrigerator. Open shelves display an array of glassware, plates, and mugs. The backsplash showcases exposed brick, adding character. A modern sink is accompanied by a sleek faucet, completing the functional and stylish space.
Apartment in Marshall
4.99 out of 5 average rating, 106 reviews

The Lofts@128:Downtown Marshall!

Welcome to ELAINE The Lofts @ 128! One of Two modern retreats nestled in the heart of Downtown Historic Marshall located above The Hub. As you enter Elaine, you'll be captivated by the tasteful blend of exposed brick walls, high ceilings, and sleek furnishings. The moment you walk out the door you are steps away from Main Street dining, shopping and entertainment in charming Downtown Marshall. Get excited about your stay, check out more pics: IG:@ thelofts_128

Top guest favorite
A serene lakeside view showcases a calm water surface reflecting the blue sky, surrounded by greenery. A sandy beach area is visible with a small fire pit nearby, while kayaks and a dock are positioned along the water's edge.
Home in Coldwater
4.93 out of 5 average rating, 126 reviews

Jake's Lake Place w/pontoon rental

Jake's Place is on a private beautiful all sports lake (all DNR regulations apply) This is the perfect spot for your next family getaway. Spring feed lake, very clean and sandy bottom. This property has access to a second empty lot for additional yard. Multiple indoor and outdoor games, paddle boat, 4 kayaks and bond fire pit for relaxing after a great day on/in the lake. Jake's place faces the west for Gorgeous sunset viewing to end your day.

Top guest favorite
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, 45 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!

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

Keep life simple at this peaceful and centrally-located home. This home is walking distance to Hillsdale Hospital, minutes from the fairgrounds, and a short drive to Hillsdale College. Make yourself at home with this family friendly retreat. This listing is for access to a private residence featuring three bedrooms, one and a half baths, as well as indoor and outdoor living, office, and kitchen spaces.

Top guest favorite
The exterior of the house features a red façade with contrasting grey stone accents. Large windows allow natural light to enter, and a front porch is accessible through a white door. Surrounding greenery includes a small landscaped area with gravel and shrubs.
Home in Hillsdale
4.89 out of 5 average rating, 289 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.

Guest favorite
A covered front porch is presented, featuring two rocking chairs positioned on a gray floor. Decorative tree-shaped wall art is affixed to the white walls, and lush greenery and vibrant fall foliage are visible in the garden beyond the railing.
Home in Jonesville
4.95 out of 5 average rating, 117 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 favorite
Home in Hillsdale
4.99 out of 5 average rating, 70 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.

Top guest favorite
Home in Hillsdale
4.97 out of 5 average rating, 30 reviews

Reedsong Cottage

Charming 2-bedroom lakeside cottage with a sleeper sofa, 1.5 baths, and stunning waterfront views. Relax on the dock, lounge outdoors, or explore the lake with included kayaks. Enjoy a full kitchen and spacious living room—perfect for up to 6 guests. Conveniently located just 2 miles from downtown Hillsdale and 3 miles from Hillsdale College.

Popular amenities for Hillsdale vacation rentals

When is the best time to visit Hillsdale?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$34,508 GYDG$35,763 GYDG$38,690 GYDG$36,599 GYDG$45,801 GYDG$40,991 GYDG$37,436 GYDG$35,553 GYDG$34,508 GYDG$35,135 GYDG$38,063 GYDG$34,717 GYD
Avg. temp-2°C-1°C4°C11°C17°C22°C24°C23°C19°C13°C6°C0°C

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.

Quick stats about vacation rentals in Hillsdale

  • Total vacation rentals

    Explore 40 vacation rentals in Hillsdale

  • Nightly prices starting at

    Hillsdale vacation rentals start at G$10,457 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Hillsdale vacation rentals include wi-fi 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!

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