Vacation rentals in Gregory

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Top-rated vacation rentals in Gregory

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

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Top guest favorite
Cottage in Pinckney
4.95 out of 5 average rating, 40 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 favorite
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.

Guest favorite
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, 479 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.

Guest favorite
Home in Chelsea
4.93 out of 5 average rating, 14 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 favorite
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
4.99 out of 5 average rating, 128 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 favorite
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, 125 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 favorite
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 favorite
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 favorite
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
4.99 out of 5 average rating, 302 reviews

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.

Top guest favorite
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
4.99 out of 5 average rating, 165 reviews

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!

Superhost
Home in Pinckney
4.93 out of 5 average rating, 14 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.

Top guest favorite
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
5 out of 5 average rating, 101 reviews

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.

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