Holiday rentals 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.

Family · Location · Long stay

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.

Location · Value · Hospitality

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.

Value · Family · Amenities

The Portage Pearl

Relax in this cottage by the lake after spending a day on the Portage Chain of Lakes. Enjoy a picnic and games at the community park located across the street with unobstructed views of beautiful Portage Lake. Watch a game on the 65" smart TV. Enjoy cooking w/ a fully equipped kitchen and propane grill. Indoor and outdoor dining areas. End the evening around the fire pit underneath the stars. There is a free boat launch nearby on the main road. In-unit washer & dryer. New HVAC in '24

Location · Value · Accuracy

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.

Value · Family · Condition

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.

Value · Family · Laundry

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.

Location · Family · Biking

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.

Family · Location · Pets

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.

Family · Value · Kitchen

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!

Value · Location · Walkability

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.

Location · Family · Condition

Frank Lloyd Wright Secluded Home

Currently, our calendar is open through DECEMBER 21, 2026. This house is a multilevel brick and cypress late period Frank Lloyd Wright house, the plan and design of which is based on the equilateral triangle. The house is situated on 2 heavily wooded acres in a secluded Ann Arbor neighborhood.

Value · Location · Parks