Vacation rentals in Hillsdale
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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$14,639 GYD per night before taxes and fees
Verified guest reviews
Over 3,080 verified reviews to help you choose
Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
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!
Top-rated vacation rentals in Hillsdale
Guests agree: these stays are highly rated for location, cleanliness, and more.
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!)
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.
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.
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.
Bear Lake Cottage ... Pontoon Available for Rent
Quaint and cozy cottage on all-sports Bear Lake in Hillsdale, MI, offering a year-round peaceful and serene getaway. Bring your boats, campers and tents; there’s plenty of room for everyone. The outdoor fire pit is perfect for campfire bonding, and in fall and winter months, enjoy the fire overlooking the lake. Cottage is on a channel to Pike Lake - a calm, private lake. Take the kayaks and SUPs exploring, or enjoy ice skating or fishing when the lake’s frozen.
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!
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.
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.
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.
The Rupp House
Make your Hillsdale County home base in one of the earliest houses in Jonesville, conveniently located 10 minutes from Hillsdale College. The house is a solid preserved house which invites you to kick off your shoes and relax. It has a full kitchen, a large dining table and beds for 6 persons. There is one bathroom which has a shower and plenty of hot water. Full kitchen. Washer and dryer.
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.
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 vacation rentals
Other great vacation rentals in Hillsdale
R&R friendly House
A Place of Rest
Cozy Cottage Near Campus
The LaFayette House (.1 miles from campus)
Lovely 6Bed 4Bath Lakefront home with Game Garage
Cowboy's Wolf Den
Relaxation Party of 2
The Bungalow in Downtown Hillsdale
When is the best time to visit Hillsdale?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$34,507 GYD | G$35,762 GYD | G$38,689 GYD | G$36,598 GYD | G$45,800 GYD | G$40,990 GYD | G$37,435 GYD | G$35,552 GYD | G$34,507 GYD | G$35,134 GYD | G$38,062 GYD | G$34,716 GYD |
| Avg. temp | -2°C | -1°C | 4°C | 11°C | 17°C | 22°C | 24°C | 23°C | 19°C | 13°C | 6°C | 0°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.
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