Holiday houses in Gregory

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.

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.

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.

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.

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.

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.

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).

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.

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!

Sunset Lakehouse Near Downtown Dining & Shops

A lakeside retreat in Brighton, Michigan. Fully renovated, this stylish lake house accommodates up to six guests. Enjoy panoramic lake views from the cozy living space or unwind in the backyard oasis with a fire pit under the sunset sky. Only 2 miles from Downtown Brighton, explore boutiques and dining options, or stroll along the waterfront. Whether it's a romantic getaway or a weekend with friends, this lakeside home ensures an unforgettable escape.

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.

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.