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Harbor Country vacation rentals

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Top-rated vacation rentals in Harbor Country

Guests agree: these vacation rentals 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! .

Sep 19 – 26

€ 183 per night

Home in Lakeside

4.96 out of 5 average rating, 157 reviews

Adorable couples escape with year-round hot tub!

3 NIGHT MIN JUNE 15 - END OF AUG! ADORABLE HOME IN LAKESIDE WAS RECENTLY REHABBED & OFFERS A SUPER CLEAN AND MODERN FEEL IN THE HEART OF HARBOR COUNTRY. GUEST HAVE ACCESS TO PRIVATE BEACH WHICH IS A 7 MIN WALK AWAY - NO CROWDED BEACHES! YEAR ROUND HOT TUB, A SUPER COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL COMPLETE THIS LOFT LIKE HOME. FULLY STOCKED KITCHEN, HIGH DEF TV, STREAM MUSIC, ETC! YOU WILL LOVE IT!

Oct 28 – Nov 4

€ 261 per night

Barn in Michigan City

4.96 out of 5 average rating, 340 reviews

The Black Pearl Great Escape Spa & Art Shop

Check out our website! thegreatescapespah.com The Black 🖤 Pearl is perfect for a Special Occasion for the Evening. Book a Couples Massage @ 3p.m. & Check into your Spa Suite @ 4 p.m. Kick your feet Up & Order in.... Or Dine Out~ This quaint property is located in a woodsy setting 5 minutes from Lake Michigan. The keyless entry door to The Black Pearl is located on the East wall of The Great Escape. Upon entry the Black Pearl door will be directly in front of you. Mini Luxury awaits!

Feb 12 – 19

€ 139 per night

Farm stay in New Carlisle

4.94 out of 5 average rating, 154 reviews

Glamping Off Grid in a Tiny Cabin on a Farm

Experience a serene and relaxing getaway in our off-grid tiny cabin on our farm. Created with the intention of slowing down (no tv, no wifi and limited electricity), enjoy wandering the fields relaxing in one of the hammocks, cooking on the outdoor fire pit, sipping coffee on the front deck and generally taking a break from modern life. If you'd like to explore the area, we are nearby popular trails and bike routes, U-pick farms, breweries & restaurants and beaches along Lake Michigan.

Jan 27 – Feb 3

€ 141 per night

Villa in Michigan City

4.9 out of 5 average rating, 127 reviews

Steps from the beach. Entire beach villa renovated

Private, ~800 sq ft, ground-level renovated beach villa with close trail access to the beach. Includes 1 BR with queen bed, 1 BR with futon & extra folding guest bed, kitchen, bathroom, & living room with small couch that converts to sleeping space if needed. Amenities: washer/dryer, free wi-fi/streaming services, 2 free parking spaces, AC/heating, self check-in, laptop friendly workspace, games, complimentary coffee/tea, beach chairs, towels, umbrella & toys, & cleaning/laundry supplies.

Dec 12 – 19

€ 141 per night

Guesthouse in New Buffalo

4.98 out of 5 average rating, 691 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.

Apr 30 – May 7

€ 104 per night

Cottage in New Buffalo

4.94 out of 5 average rating, 318 reviews

Twin Cottage A- Walk to Beach & Town!

Twin Cottage A is your home for convenience & comfort! 2 blocks from town shopping & restaurants, Church Brewing Co. around the corner, an artisanal cocktail lounge up the block and only 3700 feet to the beach! You'll have a private, fenced in backyard for the kids and/or dogs. gas grill, outdoor dining & a fire pit stocked with wood. Check out Cottage B as well for a complete look at our reviews. *Stays 28 days or longer require weekly cleaning fee added after inquiry or request

Jan 20 – 27

€ 184 per night

Cottage in Union Pier

4.93 out of 5 average rating, 280 reviews

Steps to the Beach! Screened in Porch & Firepit!

Location does not get any better than this! 90 second walk to one public beach access, and less than 5 minutes to a second! Enjoy a lazy day at the beach or head out to explore the area. It's just a quick trip to rent a kayak or paddle-board, do a bit of antiquing, golfing or climb a giant dune. There's no limit to amazing breweries, wineries, and restaurants. End your day relaxing on the giant screened-in porch or out by the firepit. What's not to love about Harbor Country!

Feb 23 – Mar 2

€ 224 per night

Cabin in Union Pier

4.96 out of 5 average rating, 292 reviews

McComb's Cabin, Union Pier, MI

Giant trees welcome you down the drive back to the secluded cabin in the woods. A contemporary cabin of steel and pine with vaulted ceiling and sky lights. Open living space, inviting queen size bed, luxury rain shower, full kitchen but no stove. A wood burning fireplace- fall through end of March and outside fire pit. Public beach a 5 minute drive away. Couples check out the cabin for anniversaries/ birthdays - Singles, seeking a simple life under the pines.

Dec 22 – 29

€ 163 per night

Cottage in Union Pier

4.95 out of 5 average rating, 271 reviews

J’s Beach House: Hot Tub & short walk to beach!

J's Beach House is < a 5 minute walk to the beach! My cottage is equipped with a private hot tub and fireplace. Enjoy the walkable town or jump in your car for a quick drive to any Harbor Country activity! Potential for rental with adjacent cottage "Riley's Retreat". *Please inquire about our other Airbnb cottage near downtown Union Pier. This cottage is a 2-bedroom plus kids loft, screen porch, hot tub, fire pit, plus walking distance to Townline Beach!

Sep 28 – Oct 5

€ 332 per night

Guesthouse in New Buffalo

4.96 out of 5 average rating, 469 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!

Mar 5 – 12

€ 153 per night

Guesthouse 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.

May 30 – Jun 6

€ 137 per night

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Popular amenities for Harbor Country vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Harbor Country

Cottage in Union Pier

4.97 out of 5 average rating, 182 reviews

"The Pines" in Union Pier: Year-round getaway

Sep 10 – 17

€ 293 per night

Cottage in Three Oaks

4.9 out of 5 average rating, 105 reviews

Private, Sun-filled Union Pier Cottage

Oct 25 – Nov 1

€ 187 per night

Farm stay in Sawyer

4.98 out of 5 average rating, 339 reviews

Your SW Michigan Modern Farmhouse Cottage Awaits

Sep 25 – Oct 2

€ 213 per night

Apartment in New Buffalo

4.94 out of 5 average rating, 163 reviews

Peach by the Beach! 1 Bdrm Apt close to downtown

Feb 5 – 12

€ 184 per night

Cabin in Michiana

5.0 out of 5 average rating, 201 reviews

Romantic Getaway in the Dunes for a Couple—Hüüsli

Sep 15 – 22

€ 314 per night

Home in Union Pier

4.92 out of 5 average rating, 105 reviews

Barn & Beach - main house ( front)

Feb 11 – 18

€ 293 per night

Chalet in Union Pier

4.93 out of 5 average rating, 175 reviews

Charming Harbor Country Chalet with Hot Tub

Jul 24 – 31

€ 376 per night

Home in Lakeside

4.99 out of 5 average rating, 101 reviews

Lakeside Retreat Nestled Among the Trees

Sep 16 – 23

€ 435 per night

Other great vacation rentals in Harbor Country

Guesthouse in Chesterton

4.96 out of 5 average rating, 114 reviews

Bro’s Place

Oct 12 – 19

€ 119 per night

Condo in New Buffalo

4.8 out of 5 average rating, 142 reviews

Lake Condo in the heart of Downtown New Buffalo

Oct 11 – 18

€ 161 per night

Home in Michigan City

4.98 out of 5 average rating, 228 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

Aug 10 – 17

€ 225 per night

Guest suite in Three Oaks

4.91 out of 5 average rating, 305 reviews

Maddie’s Place - Deluxe Guest Suite

Oct 10 – 17

€ 149 per night

Home in Trail Creek

4.98 out of 5 average rating, 65 reviews

Leo Lodge

Sep 10 – 17

€ 136 per night

Home in New Buffalo

4.98 out of 5 average rating, 47 reviews

Luxury Home Steps From Beach W/ Hot Tub & Theatre

May 9 – 16

€ 947 per night

Home in Union Pier

4.86 out of 5 average rating, 22 reviews

Fabulous Heated Indoor Pool & Tennis Court!

Jan 31 – Feb 7

€ 1,066 per night

Home in New Buffalo

4.96 out of 5 average rating, 25 reviews

Breathtaking Home on Lake Michigan, Priv Beach, 2

Jan 12 – 19

€ 833 per night

Destinations to explore