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Holiday rentals in Three Oaks

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Top-rated holiday rentals in Three Oaks

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

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Cabin in Rolling Prairie

4.87 out of 5 average rating, 135 reviews

3+ acres of Privacy, Pup heaven!7 minutes 3~Oaks!

Hello! we are 10 minutes to Three Oaks, Mi. This town is divine and very fun~ restaurants, galleries, Journeyman Distillery, Antiquing & Warren Dunes (epic hiking, dog-beaching-as private or social as you like). My artsy, sunny and cozy home welcomes you! We back up to over 3 + acres of private woods, a fresh spring fed brook and seconds from some of the best biking roads in the midwest! My place is VERY private yet 10 minutes to 3 Oaks for an evening of fun, live music & shows @ The Acorn! .

3–10 Oct

£158 per night

Guest favourite

Home in Three Oaks

4.98 out of 5 average rating, 102 reviews

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

13–20 Jun

£190 per night

Guest favourite

Guest suite in Three Oaks

4.98 out of 5 average rating, 159 reviews

The Pink Garden: In town, mod w/ amenities, yard

You'll be enchanted by this quiet town in Harbor Country! One-night stays welcome! We're a 3 minute walk to the main strip w/: • Journeyman Distillery ft. The Acorn Theater • Vickers Theater • Antique stores • Coffee shop, bakery • Food/drink • Art Galleries & a 10-20 minute drive to: • Beaches • Nature preserves • Farm stands and markets • Wineries, breweries, dispensaries • Casino We await you w/: • Fully loaded kitchen • Laundry • Fast WiFi • Smart TV • Bonfire pit • Fenced backyard

18–25 Oct

£125 per night

Guest favourite

Guest house in New Buffalo

4.98 out of 5 average rating, 692 reviews

"Tiny House" Guest House Under the Oak Trees

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

30 Apr – 7 May

Guest favourite

Home in Three Oaks

4.99 out of 5 average rating, 110 reviews

Dog Friendly Downtown Three Oaks Cottage! Fenced!

Just a short walk to charming downtown Three Oaks, home of the famous Journeyman’s Distillery and all the shops and eateries Three Oaks has to offer. It is also a quick drive to the beautiful beaches at Warren Dunes State Park and New Buffalo. This cheerful home has queen beds, a comfy sleeper sofa and a fully stocked kitchen. Plus a huge fenced-in back yard, so bring the kids or the dogs and know they are safe while you relax in the three-season room or on the outdoor deck!

12–19 Nov

£180 per night

Guest favourite

Home in Three Oaks

4.96 out of 5 average rating, 119 reviews

The Heartwood House<3 : DT Three Oaks w/Game Room

Newly renovated 1920's Bungalow loaded with character. Spacious interior with a mix of modern and vintage furnishings that will leave you relaxed and rested. Large private backyard with grill and firepit to enjoy starry Three Oaks nights. Only 4 blocks from Journeyman Distillery and close to all of the restaurants and shops in downtown. Perfect place to stay for a wedding or getaway near wineries, breweries and beaches. Come see the village that everyone is talking about!

30 Apr – 7 May

£274 per night

Guest favourite

Guest house in New Buffalo

4.96 out of 5 average rating, 470 reviews

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

28 Feb – 7 Mar

£133 per night

Guest favourite

Guest house in Sawyer

4.92 out of 5 average rating, 148 reviews

Heron's Rest hideaway close to beaches, breweries

Privacy on 11 acres of conservancy-protected land including woods, two ponds, and a river. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Fish on site. Kayak, bike, hike nearby. Ideal for nature lovers. Separated from our home by breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible.

3–10 May

Guest favourite

Home in Three Oaks

4.98 out of 5 average rating, 224 reviews

Sycamore Cottage - Hot Tub - Steps to Downtown 2BR

Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Sycamore Cottage. A few minutes walk to charming shops, restaurants, and event venues including Journeyman Distillery, The Acorn Theater, and The Social Club in Three Oaks. Three Oaks is just a ten minute drive from the beautiful beaches of Lake Michigan and thirty-five minutes to Notre Dame. Enjoy the small town lifestyle and find your own moment to getaway.

19–26 Feb

£186 per night

Guest favourite

Guest suite in Three Oaks

4.91 out of 5 average rating, 305 reviews

Maddie’s Place - Deluxe Guest Suite

Simply designed space to maximize your convenience while visiting Three Oaks. Three quarters bathroom has plenty of space. The suite features a private entrance from outside, queen bed, tv with xfinity cable and WiFi, refrigerator, microwave, dishes, sink, couch, and table to eat. We do not have a stove / oven. The coffee maker uses pods, feel free to bring your favorites! This is a private space 1/2 duplex with outside access on rte 12.

13–20 Oct

£128 per night

Cottage in Sawyer

4.93 out of 5 average rating, 207 reviews

Northwind Llama retreat “Chicken coop”

Enjoy your farm style experience- Llamas, chicken’s, dog’s and cats! 400 sq. ft. "Efficiency Suite" Revel and Relax . Rest in the queen memory foam bed complete with custom Upstate bedding. The open space living area has ample seating, desk, and full- size fridge for your libation. Private bathroom with stand up shower with exclusive Robert Jeffrey products. Your family pet is welcome! Please add your pet to rsvp !

30 Jan – 6 Feb

£117 per night

Guest favourite

Farm stay in Sawyer

4.98 out of 5 average rating, 339 reviews

Your SW Michigan Modern Farmhouse Cottage Awaits

Located in Sawyer, you can bike or drive to countless beaches, breweries, wineries, distilleries, and outdoor adventures. Afterward come home to this stylish modern farmhouse cottage that looks out onto 14 acres of scenic barn, pasture. and woods. Your home away from home has a well appointed kitchen for foodies who like to cook or great local dining options for those who don't.

10–17 Nov

£172 per night

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

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Houses

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Hotels

Stylish accommodation and amenities

Popular amenities for Three Oaks holiday rentals

Free parking on premises

Air conditioning

Stay near Three Oaks's top sights

Journeyman Distillery250 locals recommend

The Acorn85 locals recommend

Featherbone Restaurant & Lounge17 locals recommend

Harding's Friendly Market15 locals recommend

Viola Cafe34 locals recommend

Oaks Eatery27 locals recommend

Other great holiday rentals in Three Oaks

Guest favourite

Flat in Three Oaks

4.98 out of 5 average rating, 56 reviews

2BD Retreat Steps to Downtown

10–17 Jun

£160 per night

Guest favourite

Cottage in Three Oaks

4.97 out of 5 average rating, 60 reviews

Comfortable, charming vintage 2 bed/1 bth cottage

27 Aug – 3 Sept

£137 per night

Guest favourite

Home in Three Oaks

4.97 out of 5 average rating, 67 reviews

1 Block to Journeyman - Dog Friendly/Patio/Firepit

19–26 Jan

£232 per night

Guest favourite

Bungalow in Three Oaks

5.0 out of 5 average rating, 37 reviews

Cozy Designer Bungalow in Charming Three Oaks

25 Mar – 1 Apr

£153 per night

Flat in Three Oaks

4.82 out of 5 average rating, 39 reviews

The Loft at the Acorn Theater

7–14 Jan

£176 per night

Guest favourite

Barn in New Carlisle

4.97 out of 5 average rating, 39 reviews

Be Our "Country" Guest

31 Dec – 7 Jan

£151 per night

Guest favourite

Home in Three Oaks

4.98 out of 5 average rating, 50 reviews

Pet friendly stylish retreat with sauna, hot tub

5–12 Nov

£301 per night

Guest favourite

Home in Three Oaks

5.0 out of 5 average rating, 16 reviews

Dream Wedding Stay or Family Getaway - You Choose!

3–10 Sept

£726 per night

Quick stats about holiday rentals in Three Oaks

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
4.3K reviews
Nightly prices starting at
£56 before taxes and fees

Destinations to explore