Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

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Guest favourite
An open-concept kitchen and living area is showcased, featuring modern white cabinetry and granite countertops. Stainless steel appliances, including a stove and refrigerator, are visible. A breakfast bar with stools enhances the space, illuminated by recessed lighting and a nearby window allowing natural light.
Home in Harrison Township
4.83 out of 5 average rating, 66 reviews

Boaters Paradise: Stay, Sail, and Dine!

Travel Nurses Contact me for special rates Welcome to our cozy and charming three-bedroom home perfect for families, couples, or a group of friends looking for a comfortable and convenient place to stay. The driveway is 120ft+ paved. long enough for 2 trucks and 2 Bass Boats. Located across the canal, there is no dock. Walking distance to restaurants. **Pet fee is $125.00. Any additional pet is $50.00. 🚫NO PETS ON FURNITURE🚫 🚫NO CATS *HAIR ON FURNITURE THERE'S A $75 Extra Cleaning Fee.

Top guest favourite
The upper flat of a bungalow is showcased, featuring a light blue exterior with multiple windows allowing natural light. A staircase leads to a private entrance, framed by neatly landscaped bushes and seasonal foliage. Leaves cover the ground, indicating autumn's presence.
Guest suite in New Baltimore
4.93 out of 5 average rating, 188 reviews

Anchor Bay Away!

Cozy Bungalow Upper Flat in Booming Downtown New Baltimore. 2 Bedrooms, Living Room, Full Kitchen and Bath. Just a block away from Washington St. with several Restaurants, Bars, Gift Shops, Ice Cream Parlors, and the New Baltimore Historical Museum. Waterfront Park with Clean, Sandy Beach, Picnic areas, Playscapes, Fishing Pier, and Public Boat Docking. Ideal for Fishermen coming to fish the GREAT Lake St. Clair Waterway! Can accommodate 2 Truck and Trailer rigs with A/C for charging too!

Top guest favourite
A two-story cottage is depicted, nestled among lush trees and overlooking the water. Two balconies with railings offer outdoor seating. The lower level features a patio area with chairs and a dock, designed for easy access to the water. The exterior showcases a light purple facade.
Cottage in Harrison Township
4.84 out of 5 average rating, 201 reviews

Cottage on the Clinton "Fisherman's Paradise"

The Cottage on the Clinton offers a 4 bedroom, 2 full size bathrooms, with a total of 6 beds, perfect for sleeping up to 8 guests! You will be greeted with plenty of natural sunlight overlooking the Clinton River in the backyard. With an open floor plan it’s easy for you and your group to spend time together, while also finding quiet moments to yourself. This is the perfect setting for your next fishing trip, family vacation, a corporate retreat, or getaway for friends and family gathering.

Guest favourite
A wooden deck is set alongside a peaceful canal, featuring two rocking chairs positioned on a patterned area rug. Lush greenery lines the waterway, and a gentle sky fills the backdrop, creating a serene outdoor seating area.
Cabin in Grosse Pointe Park
4.99 out of 5 average rating, 153 reviews

Detroit Canal Retreat

Secluded hideaway in the “Venice of Detroit”! Perched right on the historic Detroit canal system, this urban tiny house is a cozy retreat for couples or solo adventurers. Whether you’re here to kayak, cast a line, or just kick back with a book and a breeze, you’ll find plenty to love. Located in one of Detroit’s most unique—and real—neighborhoods. This is a revitalization zone with character: some blight, sure, but also a strong sense of community, and a refreshingly diverse, welcoming vibe.

Guest favourite
A simple wooden table is paired with a matching bench, adorned with a floral arrangement in a clear vase. A textured orange runner drapes over the table. The walls feature artfully arranged woven baskets, and a large mirror enhances the sense of space.
Flat in Richmond
4.91 out of 5 average rating, 158 reviews

Richmond Reverie

Our historic apartment located in Central Downtown Richmond is a perfect stay for all occasions. Built in the 1800s this space has so much character and history. Decorated in retro vintage/ boho decor you’ll feel nostalgic and at peace while being here. The buildings downtown are beautiful and the view of Main Street will make you feel like your in a big city while still being in this quaint busy little town with so much to offer! Walking distance to bars, restaurants, and so many cute shops.

Top guest favourite
A covered porch area features comfortable seating with cushions, arranged around a modern table. A dark storage unit sits centrally, while a peaceful canal view is visible beyond the sturdy railing. Lush green grass and a well-manicured lawn complement the surrounding landscape.
Home in New Baltimore
4.97 out of 5 average rating, 29 reviews

Lake Saint Clair Cottage House

Relax and recharge at this quaint, newly updated 2-bedroom, 2-bathroom cottage nestled on a peaceful canal with direct access to Lake St. Clair. Whether you're here to fish, boat, or just unwind, this cozy retreat has everything you need. Direct access to Lake St. Clair is perfect for world-class fishing & boating. Covered porch for morning coffee or evening wine. Peaceful, quiet neighborhood. Fully stocked kitchen, 2 comfy living spaces Just minutes from shopping, dining, and freeway access.

Guest favourite
Home in New Baltimore
4.85 out of 5 average rating, 125 reviews

Fishmen's Dream! Lake St Clair House! Boat Space!

Welcome to our serene retreat! Nestled in a peaceful neighborhood, our renovated space invites you to unwind and soak in the tranquility of your surroundings. Bring your boats! Formerly owned by a minister and forestry manager, this home exudes a sense of quiet contemplation and a connection to nature that you'll undoubtedly appreciate. From the moment you step inside, you'll be pleased by the tasteful and stylish design that reflects both the home's history and modern comfort.

Guest favourite
A serene outdoor area features a well-maintained lawn with neatly arranged stone pavers. A small dock is visible along the water, where boats are moored. The horizon showcases a calm lake under a partly cloudy sky, providing a peaceful retreat.
Home in New Baltimore
5.0 out of 5 average rating, 10 reviews

The Buoy Bungalow

Welcome to your perfect lakeside getaway! Nestled directly on the shores of Lake St. Clair, our cozy yet spacious cabin offers stunning water views, peaceful surroundings, and everything you need for a memorable stay. Whether you're fishing, paddling, swimming, or just soaking in the lake breeze, this cabin offers the perfect blend of comfort and nature. Enjoy long days on the water and peaceful nights by the fire. Book your stay and experience lakeside living at its finest.

Guest favourite
Home in Harrison Township
4.95 out of 5 average rating, 107 reviews

Cozy Canal Cottage - Minutes to Lake St. Clair

A vacation home on the canal of Lake St. Clair but still close to the city for a day of fun-filled adventures. Gather with friends and family to share memories in our cozy cottage. Imagine a morning cup of coffee dockside or an evening bonfire to end the night. The house is spacious and comfortable, with plenty to keep everyone entertained and high-speed internet for streaming! Whether you're looking for a fishing trip or a relaxing stay, we've got you covered.

Top guest favourite
A spacious common area is shown with a large wooden dining table surrounded by chairs. A comfortable brown sofa is positioned nearby, complemented by a cozy throw. White cabinetry lines the wall, and a bed can be seen, enhancing the multifunctional space.
Barn in Harrison Township
4.98 out of 5 average rating, 130 reviews

Spirit Haven Nurture your spirit

We are located on the end of a quiet road surrounded by 155 acres of woods, marsh and wildlife; it is a serene and idyllic space for rejuvenation, healing and connection. The land has been repeatedly identified as Sacred Grounds, a space of ancestral heritage used for centuries for celebrations of gratitude and honoring life of all forms. As such the property embodies high spiritual energy, including the existence of several vortices.

Top guest favourite
A graceful swan glides across calm waters, leaving ripples in its wake. The reflection of the swan can be seen on the surface, enhancing the serene ambiance of the canal. Wooden dock planks are visible in the foreground, leading towards the water.
Tiny home in New Baltimore
4.95 out of 5 average rating, 102 reviews

Waterfront Tiny Home + Dock

Fall Special! Book a 3 night stay w/ 20% off through the end of October. Welcome to our 360 sq ft renovated tiny home on the canals of Lake St. Clair, MI. The backyard features a fire pit, BBQ grill, and guests can bring boats up to 24ft long and dock them right out back. Bring an extension cord to plug into the back of home to charge batteries. Home also offers trailer and vehicle parking.

Top guest favourite
Home in Harrison Township
4.89 out of 5 average rating, 138 reviews

-The Lake house- Canal, Kayaks, Parking, Lake

New Photos for 2026! This canal-front home is the perfect setting for your ultimate lake experience ideal for fishing trips, boating weekends, and unforgettable family gatherings. With ample on-site parking for trucks and trailers, this property is perfectly suited for boating enthusiasts, anglers, and adventure seekers looking to make the most of Lake St. Clair.

Popular amenities for Chesterfield holiday rentals