
Holiday houses in Gregory
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Top-rated holiday rentals in Gregory
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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.

Charming Retreat in Downtown Chelsea 4 Br 2 Ba
A beautiful, remodeled 100+ year old home in the charming downtown area of Chelsea. Located near the new DTE bike trails, a short walk to downtown, and just minutes from great hiking in the Waterloo Recreation Area. Our home will be spotless and well sanitized for your stay. We provide snacks, water bottles, tea and coffee. If you need any baby or toddler items, we can provide things like baby gates, bed rail, pack n play, high chair, etc. A Christmas tree can be provided for holiday bookings.

MOD Mid Century 1964 A-frame with game room
1964 Mid Century A-Frame - romantic getaway. Short walk to lake, large wooded lot, outdoor fire pit, dining, BBQ grill, hot tub & bikes. Large bathroom w/ jacuzzi tub, open floor plan w/ large kitchen & living area w/ electric fireplace. Two upstairs bedrooms. Master has queen sized bed, work space & balcony. Front bedroom w/2 futons & overlooks the living room. Basement game room w/ sauna, pool table, foosball, shuffleboard, Jenga & laundry. Close to shopping, golf, ski resort, cider mill.

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.

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.

Huron River Lodge
Custom designed, private home featuring scenic views in a retreat like setting nestled along the Huron River just minutes from downtown Ann Arbor. The luxurious, light-filled space boasts two decks, hot tub, fully equipped kitchen, fireplace, and EV charging. This very special property is located along the Border-to-Border Trail and Amtrak line just minutes from US-23, M-14, and US-94. Immerse yourself in a unique environment of beauty and convenience with amenities for all seasons.

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).

Peaceful Lake Retreat with Sauna
Our lakefront apartment and property overlooks a peaceful canal and lake that is surrounded by woods. We are connected to the all sports Halfmoon Lake Chain with access to 8 lakes. Our property is the perfect place to start your paddling adventure with lots of nature to experience! We are in the heart of the Pinckney Recreation Area, home to the Potawatomi Trail. Great for biking, hiking, cross country skiing and snowshoeing. The perfect place to sit, relax, and watch the sunset.

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.

Brushstrokes by the Lake Cottage
Charming and fully renovated rustic cabin nestled by the serene lake. Offers an up-north feeling without the long drive! Futures: Wake up to breathtaking lake views and natural beauty. Swim, kayak, or paddle board for some fun on the lake. Relax by the fire pit in the evening or enjoy a meal. ~10 minutes away from Pine Knob concerts and ski resort. Only ~15 minutes from Clarkston's delightful restaurants.
Popular amenities for Gregory holiday rentals
Other great holiday rentals in Gregory

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Cozy Cottage Lakeside

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Exquisite Condo in Howell

Frank Loyd Wright Inspired Studio
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- Michigan Stadium
- Detroit Zoo
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- Kensington Metropark
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- University of Michigan Museum of Natural History
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