Holiday houses in Gregory

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Top-rated holiday rentals in Gregory

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

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Superhost

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

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.

FamilyValueHeating

4.91 out of 5 average rating, 222 reviews

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

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.

FamilyValueBarbecue

4.97 out of 5 average rating, 138 reviews

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

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.

FamilyLocationAccuracy

4.93 out of 5 average rating, 131 reviews

Guest favourite

Home in Pinckney

Lakefront cottage

Charming lake front cottage on Watson lake. Watson lake is part of the Halfmoon lake chain of lakes. Enjoy the amazing view of the lake and the state land beyond. Access Half Moon, Bruin, Blind, Woodburn, Patterson and Hiland Lake all in one day. Recently remodeled. New stamped concrete sidewalk and patio. Three bedrooms, bath and a half for a family or guests. Large living room area, dining and kitchen area with an open concept that takes full advantage of the lake views.

FamilyLocationCheckout

4.95 out of 5 average rating, 74 reviews

Guest favourite

Cottage in Gregory

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.

FamilyLocationCleanliness

4.94 out of 5 average rating, 34 reviews

Top Guest favourite

A peaceful entrance is framed by lush greenery, leading up wooden steps. Ferns and hostas line the pathway, guiding guests toward a lower-level apartment. The home, nestled among trees, features a large balcony and expansive windows, inviting natural light into the living spaces.

Apartment in Ann Arbor

Dream home in the woods (Sister lakes area)

Rental license # STR26-0389 We are renting out a 2 Bedroom Appartment (lower level) in our house/duplex. It has a separate entry and is located in a tree rich area. A natural area begins right behind the house. The sister lakes are in a 3 min walking distance. The apartment is conviniently located in Ann Arbor - 2.2 mi to Downtown - 3.5 mi to the Big House - 2.8 mi to UofM central campus A bus stop and a great coffee place are in walking distance.

ValueFamilyComfort

4.99 out of 5 average rating, 314 reviews

Top Guest favourite

A charming farmhouse with a distinctive green roof is set against a blue sky. The entrance is framed by stone pillars, leading to a gravel driveway that runs alongside bales of hay. White fencing encircles the property, surrounded by lush greenery.

Farm stay in Dexter

Stay on a charming 250-acre working farm!

Stay in a lovely restored farmhouse on 250+ acres of land in Dexter, MI. We are a working cattle farm with an orchard, garden, resident farmer (in a house on the property), acres of woods and miles of country roads. Lots of space! We are near the end of the Border to Border trail going to Dexter now and soon all the way to Ann Arbor! Located across the street from the Michigan Sailing Club. We're a convenient stay for University of Michigan events!

ValueLocationSleep quality

4.99 out of 5 average rating, 172 reviews

Top Guest favourite

The historic brick chapel is framed by vibrant landscaping, featuring blooming flowers and lush greenery. Large stained glass windows are visible, accentuating the architectural details of the building. A welcoming sign stands in front, inviting guests to explore the unique space.

Home in Fowlerville

Kelmscott Chapel

This historic structure was built in 1909 for the local catholic parish and served as such until the 1970's. A portion of the church was then converted to a residence and has also served as a wedding venue for over twenty years. Now called Kelmscott Chapel, a nod to William Morris and the arts and crafts movement, you will find warm and inviting accommodations. Complete with stained glassed windows, spiral staircases, decorated with art and antiques.

LocationValueDecor

4.99 out of 5 average rating, 160 reviews

Top Guest favourite

An aerial view showcases a spacious yard leading to Zukey Lake, surrounded by lush trees and nearby houses. A hammock is visible on the left, and a cozy gazebo sits centrally positioned. The driveway accommodates a parked orange vehicle, adding a pop of color to the serene setting.

Guesthouse in Pinckney

Bon Jodi's Dreamy Escape (sleeps 7)

Stop here. You've found the winter wonderland and summer dreamland. There's so much to offer every season including Zukey lake fun, a variety of games, a large bonfire pit, + seasonal heated igloo for a unique fall and winter experience. Enjoy our indoor bar with two TVs, a pool table, arcade games, and cornhole. New flooring placed Jan 2026 & new felt on pool table. Kayaks, paddleboards, water bike, and paddle boat available at no extra charge.

LocationFamilyQuiet

4.94 out of 5 average rating, 146 reviews

Top Guest favourite

The exterior of the house is shown, featuring a multilevel design with a combination of brick and cypress materials. Steps lead up to the entrance, surrounded by lush greenery. A broad roof with overhangs emphasizes the unique architectural style.

Home in Ann Arbor

Frank Lloyd Wright Secluded Home

AS OF SEPT 15, 2026. Airbnb has changed how the host presents their pricing structure. ALL fees are now included in the posted nightly rental charges, including the separate SERVICE fee the client formerly paid directly to AIrbnb. Guest pays no additional fees. OUR OVERNIGHT RENTAL PRICES HAVE NOT CHANGED, but are now adjusted to offset the fees now collected from the host. Currently, our calendar is open through JANUARY 2, 2027

ValueFamilyBathroom

4.91 out of 5 average rating, 124 reviews

Top Guest favourite

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

Relax with the whole family at this peaceful cottage. Enjoy the beautiful lake views from the balcony, take a walk on our private secluded boardwalk down to the lake, enjoy a fire, soak in the tub, play a game in the spacious activity room, go for a paddle around the lake, or just curl up and get cozy and enjoy the sounds of nature and the beautiful wildlife.

LocationFamilyCheckout

5.0 out of 5 average rating, 103 reviews

Top Guest favourite

The exterior view of the Goetsch–Winckler House showcases its distinct architectural lines amidst vibrant autumn foliage. A cantilevered carport extends gracefully, blending natural materials with the surrounding landscape, while trees display a spectrum of fall colors, enhancing the serene setting.

Home in Meridian charter Township

Frank Lloyd Wright’s Goetsch–Winckler House

Experience a rare glimpse of Frank Lloyd Wright’s vision for Usonia 🟥 Designed by Frank Lloyd Wright and built in 1940, the Goetsch–Winckler House is widely considered to be one of the most elegant examples of Wright’s Usonian ideal.

LocationValueDecor

5.0 out of 5 average rating, 131 reviews