Family-friendly holiday rentals in Hillsdale

4.97 out of 5 average rating, 369 reviews

A hot tub is positioned on a wooden deck, overlooking a serene lake at dusk. String lights are draped above, casting a warm glow. Reflections of trees and a dock are visible on the calm water's surface, enhancing the tranquil atmosphere.

Home in Bronson

Private Lakefront, Hot Tub, Kayaks

*Lakeside Luxury Awaits: Your Tranquil Escape* Immerse yourself in the serenity of lakeside living at this stunning retreat, perfectly positioned just 10 minutes from the natural beauty of Pokehagen State Park. This 3-bedroom haven offers an unparalleled escape for families and friends seeking relaxation and adventure. Wake up to breathtaking lake views from almost every room. The sunroom beckons with its cozy ambiance, ideal for enjoying your morning coffee or losing yourself in a good book.

Indoor spacesFamilyHot tub

4.97 out of 5 average rating, 144 reviews

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

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.

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 61 reviews

Home in Hillsdale

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!)

Indoor spacesKitchenTV

4.96 out of 5 average rating, 270 reviews

A teal skoolie sits parked on a grassy area, with a shaded wood deck extending from its side. Two red outdoor chairs are positioned nearby, and decorative lights are strung overhead, adding a cozy ambiance to the serene outdoor setting.

Bus in Grass Lake

The Feral Skoolie

Nestled on 4 acres and located in the heart of Waterloo recreation area, this 280sq ft skoolie boasts comfort and eclectic energy! Sure to please the outdoor enthusiast, the property is surrounded by public land with the Pinckney Waterloo Trail crossing at the end of our driveway, and several nearby lakes. Located 30 minutes to Ann Arbor, 15 minutes to downtown Chelsea which offers plenty of great eats and drinks, 20 minutes to downtown Jackson, 10 minutes to Sandhill crane winery.

KitchenIndoor spacesValue

4.97 out of 5 average rating, 118 reviews

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

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.

KitchenFamilyCheck-in

A charming lakefront house features a dark exterior with a welcoming red door. The manicured lawn leads from a gravel path to the entrance, with serene water visible beyond. Surrounding trees provide shade, enhancing the peaceful setting by Huyck Lake.

4.92 out of 5 average rating, 158 reviews

Cozy Lakefront Cottage on Huyck Lake

Relax with the whole family at this peaceful, cozy place! 3 bedrooms 1 bath. Living room has a comfortable couch that pulls out into a bed along with additional seating. Full bath, kitchen, and laundry room are fully stocked for your comfort and enjoyment. Huyck Lake is a quiet, no wake lake. This house is perfect for a small to medium sized family or a romantic getaway. Master bedroom and guest bedroom have mounted TV’s. Family friendly. No to the following: pets, smoking, parties.

Indoor spacesFamilyView

Superhost

A cozy lakefront home is visible, featuring a welcoming front deck with decorative bunting. A small lighthouse-style feature is situated next to the stone steps leading up to the entrance. A blue shed rests in the foreground, surrounded by landscaped rocks and greenery.

Home in Quincy

Stunnnig House on Marble lake with private beach🏖

Our cozy lake front home offers both summer and winter fun with amazing views of beautiful Lake Marble. The direct water access allows family and friends the ability to swim, fish, and boat with ease and convenience. Our 4 bedroom home sleeps up to 10 comfortably with 3 full bathrooms. You will find our home fully furnished with everything you would need. 17 miles of lakes connected by channels. Minutes away from Allen Michigan, the Antique Capital of the World.

KitchenFamilyOutdoor spaces

4.85 out of 5 average rating, 190 reviews

4.91 out of 5 average rating, 159 reviews

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.

Apartment in Hillsdale

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.

KitchenIndoor spacesBathroom

A waterfront cabin is depicted with a large glass front, allowing ample natural light inside. Lush green grass surrounds the house, complemented by tall trees. A pathway leads to a spacious deck area with outdoor seating and a grill, enhancing outdoor relaxation opportunities.

4.84 out of 5 average rating, 134 reviews

Coldwater Lake Waterfront Cabin - Boat for Rent

Relax with the whole family at this peaceful waterfront lakehouse, with walk-in, sandy beach lake access. Boat available to rent, and space available for your boats. Spacious yard with plenty of parking. Coldwater Lake is over 1,600 acres of all-sports fun on desirable South Chain of Lakes in Coldwater, MI. The chain is 17 miles, traversable via pontoon or speedboat! The Cabin includes 3 bedrooms and 2.5 baths.

FamilyIndoor spacesView

4.89 out of 5 average rating, 295 reviews

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

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.

KitchenFamilyTV

4.95 out of 5 average rating, 124 reviews

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

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.

KitchenFamilyAmenities

4.96 out of 5 average rating, 458 reviews

A charming white structure with a light grey roof is set against a backdrop of lush green grass and large trees. An American flag is displayed at the entrance, and a decorative stone feature is visible in the background, contributing to the property’s rustic character.

Home in Parma

Stay In An Old Train Depot - Gidley Station!

Be adventurous and stay in rustic old Gidley Station. It was moved to "Trail Acres" in the 1920's and was converted to a house. It has a unique but spacious floor plan, and is on a property that we have been working hard to restore for the last few years. PLEASE READ FULL DESCRIPTION BEFORE BOOKING!

FamilyIndoor spacesCheck-in

Popular amenities for Hillsdale family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cottage in Manitou Beach-Devils Lake

Lakefront Getaway: Private dock, HOT TUB & kayaks

KitchenFamilyCleanliness

4.99 out of 5 average rating, 102 reviews

4.92 out of 5 average rating, 215 reviews

A charming lake house is set amidst vibrant fall foliage, highlighting warm colors against the greenery. The home features large windows, a spacious deck, and is surrounded by trees, while kayaks are seen on the shoreline near a gentle slope leading to the water.

Home in Grass Lake

Secluded Lakehouse w/ Hot Tub, Sauna & game room

Indoor spacesFamilyTV

5.0 out of 5 average rating, 103 reviews

The cottage exterior showcases a charming design with light green siding, decorative eaves, and a spacious driveway. Lush greenery surrounds the property, and large windows create an inviting feel. The background features trees and hints of the tranquil lake, enhancing the serene setting.

Cottage in Grass Lake

Peaceful 3 Bedroom Cottage with Lake Access

KitchenFamilyHiking

4.97 out of 5 average rating, 147 reviews

Home in Albion

Lakefront Wonderland | Dock, Game Room & Hot tub

KitchenIndoor spacesPets

Guest suite in Battle Creek

A modern living room features two seating areas with comfortable sofas complemented by colorful pillows. A large flat-screen TV is mounted on the wall above a stylish electric fireplace. A glass coffee table and bar-height seating enhance the inviting atmosphere.

Couples spa retreat suite getaway. Hot tub

Indoor spacesKitchenHot tub

4.92 out of 5 average rating, 229 reviews

4.91 out of 5 average rating, 259 reviews

Home in East Leroy

Quiet Getaway w/ Hot Tub + Fire Pit | Lake Access

KitchenIndoor spacesPets

4.96 out of 5 average rating, 26 reviews

Cottage in Jonesville

Farm Cottage with Hot Tub, Sauna, Flower Fields

FamilyIndoor spacesCheckout

4.98 out of 5 average rating, 62 reviews

A wooden hot tub is situated in a bright, airy space. Skylights and string lights illuminate the area, creating a cozy ambiance. Surrounding the tub, wooden steps provide easy access, and large windows showcase views of the snowy outdoors.

Home in Brooklyn

The Enchanted Schoolhouse

KitchenIndoor spacesNearby

Family- and pet-friendly home rentals

A charming two-story cottage is set amidst lush green trees, featuring a spacious deck that overlooks a well-kept yard. The exterior is painted in a warm orange hue, complementing the natural surroundings. The structure is framed by tall trees, offering a peaceful retreat atmosphere.

4.96 out of 5 average rating, 117 reviews

Baughman's Cove

Indoor spacesFamilyAmenities

4.94 out of 5 average rating, 132 reviews

A secluded cabin is surrounded by trees adorned with vibrant autumn leaves. A picnic table is positioned nearby, complementing the natural setting. The cabin features large windows, providing views of the forest, and a wooden entryway leading to the porch.

Tiny home in Tekonsha

Little Cabin in the Woods-Quiet

Indoor spacesKitchenAccess

4.97 out of 5 average rating, 339 reviews

A rustic cabin with a log exterior is surrounded by a well-kept lawn. The front porch features decorative planters with greenery and flower beds. Large windows are visible, allowing natural light to illuminate the interior.

Cabin in Archbold

20a Cabinn - Private cabin on 10 woodland acres

Indoor spacesFamilyRiver

4.89 out of 5 average rating, 176 reviews

The front room features wooden paneling and large windows offering views of the outdoors. A comfortable armchair is positioned near a wooden bench, with decorative nautical elements enhancing the space. Light is allowed in by the windows, creating a bright and inviting atmosphere.

Cottage in Coldwater

Lakefront Nostalgic Cottage

FamilyKitchenOutdoor spaces

4.87 out of 5 average rating, 159 reviews

The exterior of a modern, rustic home is presented, featuring a combination of dark wooden panels and light-colored siding. A welcoming entryway is accentuated by a covered porch and a cheerful front garden with flowers. A garage is positioned to the left of the entrance.

Home in Fremont

Newly Designed Beach Front Get Away

FamilyIndoor spacesBarbecue

4.76 out of 5 average rating, 217 reviews

A vibrant two-story cottage with yellow siding stands beside a tree. A grassy area with chairs is visible in front, leading to a wooden dock along the lake's edge. Nearby houses are visible, showcasing a blend of architectural styles.

Cottage in Tipton

Cozy Cottage Getaway on Evan’s Lake

FamilyKitchenDecor

4.94 out of 5 average rating, 183 reviews

A spacious field is dotted with wildflowers and vibrant greenery, creating a serene landscape. In the background, a quaint yellow house is visible, framed by lush trees against a colorful sunset sky.

Tiny home in Chelsea

Cozy Tiny House on Centennial Farm

KitchenFamilyAccess

4.88 out of 5 average rating, 207 reviews

The living area features large windows framed with wooden trim, allowing natural light to fill the space. A light-colored sofa is positioned adjacent to a floor lamp, complemented by a side table and a woven area rug that adds texture to the hardwood floor.

Apartment in Marshall

Beautiful Studio

KitchenFamilyRiver

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 457 reviews

An outdoor seating area features a comfortable green sofa accompanied by a stone fireplace. Lush greenery surrounds the space, with a view of the lake and boats in the distance. Flower pots add color, and a peaceful atmosphere is suggested.

Apartment in Clarklake

Turtle Cove Lakefront, pool, hot tub, Sauna!

FamilyIndoor spacesParking

4.9 out of 5 average rating, 309 reviews

Home in Grass Lake

LIL Carrot- hot tub, pets welcome

KitchenIndoor spacesDecor

4.81 out of 5 average rating, 175 reviews

A poolside view showcases a well-maintained in-ground pool surrounded by lounge chairs and tables. A hot tub and a large blue umbrella provide shade. The white exterior of the attached apartment is visible, with multiple windows reflecting natural light.

Guest suite in Jackson

Heated Pool /Hot Tub Villa

KitchenFamilyHospitality

5.0 out of 5 average rating, 23 reviews

Home in Tipton

Great Wood Lodge

FamilyKitchenWi-Fi

Superhost

Home in Adrian

Oasis Retreat with Pool and Sauna!

Indoor spacesFamilyWalkability

4.81 out of 5 average rating, 21 reviews

Superhost

A refreshing swimming pool is surrounded by a patio area featuring shaded seating for dining. A white fence offers privacy while potted plants add a touch of greenery. The pool's clear water reflects the surrounding trees under a partly cloudy sky.

Home in Adrian

Bent Oak Estate

FamilyIndoor spacesBarbecue

4.55 out of 5 average rating, 33 reviews

4.96 out of 5 average rating, 85 reviews

A spacious living area features large windows that allow natural light and views of the indoor pool. Modern furniture includes a comfortable sofa and a sleek desk. The kitchen is visible, showcasing wood cabinetry and stainless-steel appliances.

Home in Jackson

Annie's Place behind the winery

KitchenFamilyCondition

A spacious outdoor area is featured, showcasing a large heated saltwater pool framed by a stone pathway. The house displays a combination of neutral-colored siding and large windows, providing ample natural light. Comfortable lounge chairs are positioned around the pool, complemented by shaded seating under a red umbrella.