Holiday rentals 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
4.95 out of 5 average rating, 39 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.

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
4.92 out of 5 average rating, 213 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.

Top guest favourite
An updated Victorian home is depicted, featuring a light blue exterior with white trim and decorative gables. A red front door provides a pop of color. Lush greenery surrounds the property, and flower boxes adorn the windows. A well-maintained lawn invites relaxation.
Home in Chelsea
4.95 out of 5 average rating, 61 reviews

The robot house

In the heart of downtown Chelsea, walking distance to restaurants, shopping, wedding venue & more! Enjoy weekly farmer's markets, summertime live entertainment on Thursday evenings. Historic victorian home has been updated and is clean & comfortable w/well-equipped kitchen & plenty of common space for entertaining & 2 full baths. Each of the 2 bedrooms have a queen bed & there is a queen size sofa sleeper in the living room. There is a washer and dryer available for your use in the basement

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, 266 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.

Top guest favourite
Home in Chelsea
5.0 out of 5 average rating, 13 reviews

Entire home in downtown Chelsea!

Your family will be close to everything when you stay at this centrally-located place. Just two blocks from the wedding venue: The Collins Off Main. Also, a 5 minute walk from The Grateful Crow, and only 8 minutes from Smokehouse 52 BBQ and The Common Grill. If you are looking for longer term lodging for a rehabilitation visit at The Keiser Clinic, this is the perfect place. Just a quick 5 minute walk. Ask about discounted rates! We have plenty of hiking/biking trails in and around town.

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.
Flat in Chelsea
5.0 out of 5 average rating, 127 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.

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
4.93 out of 5 average rating, 124 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.

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, 440 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).

Guest favourite
A bright 3-season room features large windows that offer views of the outdoors. Comfortable seating, including a sectional sofa and a wooden coffee table, provide a relaxed space. A decorative rug covers the floor, and simple wall decor enhances the welcoming atmosphere.
Cottage in Gregory
4.94 out of 5 average rating, 32 reviews

Lake house with Up North feel close to SE Michigan

Relax with your family and friends at this tranquil cottage. Start your day reading and enjoying coffee in the 3-season room. Explore the lake via kayak or SUP. Take a dip in the water in the beach area or catch fish off the dock or in the stream. Inside enjoy the foosball table, keyboard, full complement of games and chef's kitchen. Nearby is the DTE mountain biking trail and hiking trails and Huron River. Chelsea, Dexter and Ann Arbor are all within 15-30 minutes.

Top guest favourite
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
4.94 out of 5 average rating, 179 reviews

Cozy Tiny House on Centennial Farm

“I feel thin. Sort of... stretched. Like butter scraped over too much bread.” ~ Bilbo Baggins to Gandalf~ If this is you right now, you've come to the right place. Blue Door Guest House is designed to be a place where very tired people can come and rest. The Camino de Santiago is a special place for us and this guest house is our version of a pilgrim’s albergue. PLEASE READ GUEST ACCESS SECTION BEFORE BOOKING

Guest favourite
Home in Pinckney
4.92 out of 5 average rating, 13 reviews

Peaceful Lakefront Retreat with Hot Tub

Escape to this serene lakefront home with 2 bedrooms, 1 bath, and a pull-out couch. Bright kitchen, cozy living area, and screened porch with lake views. Kayak, paddle boat, life vests, fire pit, and gas grill included (no boat rental). Access to the hot tub all year. TV with streaming and WiFi. Quiet, family-friendly community—perfect for families, couples, or friends seeking a peaceful lakeside getaway.

Guest favourite
Flat in Jackson
4.93 out of 5 average rating, 45 reviews

New Listing - Modernized Farmhouse!

Peaceful setting - minutes to downtown Jackson! This listing is the complete lower unit, spacious and easily accessed. The original farmhouse character has been preserved with modern upgrades to make for a commodious and comfy stay! Semi rural setting and centrally located. 20 - 40 minutes to the surrounding communities of Mason, Lansing, Ann Arbor, Brooklyn, Albion and Marshall.

Popular amenities for Stockbridge holiday rentals

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  4. Ingham County
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