Holiday houses in Stockbridge

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Top-rated holiday rentals in Stockbridge

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

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Top Guest favourite
Cottage in Pinckney
4.97 out of 5 average rating, 32 reviews

Cedar Valley Cottage - Ideal Location.

Take it easy at this unique, tranquil, secluded, and pet-friendly getaway. Situated at the edge of Pinckney Rec Area, you have it all: hiking, biking, swimming, and boating at Silver Lake. In the winter hiking and ice fishing! Pinckney (7 minutes), Dexter (12 min), Chelsea, (20 min), Ann Arbor (25 min), Brighton/Howell (25 min) This 450' cottage with a spacious feel is nestled in its own wooded valley. You can grill, make a bonfire, or just enjoy the quiet. Wildlife abounds year round.

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Top Guest favourite
A spacious exterior view of a light grey home features a welcoming front porch with a small entryway. Adjacent to the porch is a two-car garage on the left. Blue shutters complement the windows, which reflect the open sky. A large driveway provides ample parking.
Apartment in Dexter
4.98 out of 5 average rating, 52 reviews

Dexter Retreat Spacious 1bd Apt outside Ann Arbor

Best of the country and minutes from Ann Arbor & Dexter. 1000 sg ft 1 bd rm private apartment attached to main home on 10 acres with private entrances and garage. 20 minutes to the Big House Stadium, Downtown Ann Arbor and University of Michigan campus and hospital. Bedroom features Select Comfort California King bed split w/dual settings 2 xl twins adjustable bases. Plenty of room for air mattresses in the living room. Lovely country view of red barns and gorgeous sunrises and sunsets.

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Guest favourite
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
4.93 out of 5 average rating, 203 reviews

Secluded Lakehouse w/ Hot Tub, Sauna & game room

Get away to the quiet of a lake in a secluded paradise! Enjoy an amazing panoramic view of Little Pleasant Lake while soaking in a hot tub and chilling out in a steaming barrel sauna in the woods. Kayak and fish for hours. Hike the area trails in fall leaves or quiet snow. Light a bonfire after games of corn-hole and table tennis. Unwind on the upstairs balcony with a glass of wine and lake sounds. This is the escape you’ve been needing. Perfect for romantic couples and family vacations.

FamilyLocationOutdoor spaces

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, 470 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.

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Guest favourite
Colorful tulips in shades of pink and white are prominently displayed in the foreground, with a historic clock tower in the background. Bright blue skies create a clear atmosphere, enhancing the overall charm of the scene.
Home in Chelsea
4.86 out of 5 average rating, 36 reviews

Downtown Living - 2nd story unit

Newly renovated historic home in charming downtown Chelsea. This beautiful second story, two bedroom unit is just steps from quaint small town shopping, dining, and entertainment; only 20-30 minutes to either Ann Arbor or Jackson on the highway; and if you are looking for outdoor adventures - the border to border trail and/or the Waterloo Recreation Area (the largest state park in the lower peninsula offering trails, lakes, mountain biking (DTE Energy Trail) and more) are just minutes away!

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Top Guest favourite
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
4.97 out of 5 average rating, 263 reviews

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.

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Top Guest favourite
The spacious living area features a light-colored sofa and two patterned armchairs. A television is positioned on a dark media unit, flanked by shelving displaying books and decor. Soft lighting illuminates the cozy carpet, while a decorative rug adds warmth to the space.
Apartment in Mason
4.97 out of 5 average rating, 71 reviews

Wagon Wheel Retreat

Enjoy a cozy, very private stay in the garden level apartment of our home, on a 10 acre beautifully wooded, wildlife filled, property. This is a one bedroom suite with a sleeper sofa, allowing up to four guests . The kitchenette includes a refrigerator, microwave, toaster oven/air fryer, and coffee bar, and the tv has streaming for your viewing enjoyment. WIFI and workout area to start your day! The patio area includes an eating area, and hot tub (open all year!), all very private.

FamilyLocationHot tub

Top Guest favourite
The modern kitchen and dining area features a large farmhouse table surrounded by light-colored chairs, complemented by a wooden bar with four stools. Natural light fills the space through expansive windows, providing views of the outdoor surroundings. Stylish pendant lights enhance the inviting atmosphere.
Apartment in Chelsea
5 out of 5 average rating, 126 reviews

Chelsea Lake House, Game Room, & Pontoon-rental

Come bike, hike, fish, kayak, boat and have a fire right on the shore of the lake, yet close to picturesque downtown Chelsea (3 miles) that features bars, shopping, excellent restaurants and we’re a short drive to downtown Ann Arbor/UoM Stadium (18 miles). We cater to families and business people alike with a fully renovated home, kayaks (5), paddle boat (life jackets provided), game room with ping pong, darts, table for poker, stone fire pit, etc. PONTOON RENTAL NOW AVAIL for addit fee.

ValueFamilyHiking

Top Guest favourite
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
4.96 out of 5 average rating, 76 reviews

Annie's Place behind the winery

Welcome to Annie’s Place! Enjoy the sights and sounds of our family winery and vineyard, as well the relaxation of being in the country. Annie was my aunt and one of the founding members of Sandhill Crane Vineyards. She loved pouring wine for our guests, and they loved her wit and sass! We frequently enjoyed sitting on her porch sipping on a glass of wine or a cocktail. Annie passed away in 2022 but her memory lives on with her family and everyone who loved her. Have a toast to Annie!

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Top Guest favourite
The spacious living area features a large sectional couch adorned with various patterned throw pillows. A light wooden coffee table is centered on a decorative area rug, while large windows provide abundant natural light and views of the surrounding greenery.
Home in Howell
4.92 out of 5 average rating, 119 reviews

Plant-Filled Small Farm Guest House

Take it easy at this unique and tranquil getaway. Located 5 minutes from downtown Howell on a micro flower farm. Enjoy a serene vacation walking through the fields and napping in hammocks. The kitchen is stocked with everything you need for a foodie weekend and produce from the farm will be provided when in season. Great location to local breweries, festivals, shopping, and so much more. This listing does include two rambunctious puppies who love to meet you, kisses, and head scratches.

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Top Guest favourite
Treehouse in Ionia
5 out of 5 average rating, 88 reviews

Tree Vistas Treehouse in Ionia Michigan

Nestled within six acres of beautiful woodlands right along the Grand River, time seems to pause, allowing us to share precious moments that foster deeper connections and create lasting memories at Tree Vistas. Our Winding Springs Treehouse comfortably sleeps 6, while also being fully ADA accessible. Nestled 13-feet above ground, the Treehouse features a spiral staircase leading to the loft, stunning views of the stream and hills from the master bedroom, and many other great amenities.

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Top Guest favourite
The exterior of the bungalow showcases a white siding with a bright red door and barn quilt design. A small patio area features a glass-topped table surrounded by four metal chairs, nestled in a grassy lawn with surrounding greenery.
Bungalow in Jackson
4.95 out of 5 average rating, 432 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).

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Popular amenities for Stockbridge holiday rentals

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