Holiday rentals in Harbor Country

5 out of 5 average rating, 199 reviews

Farm stay in Vandalia

One of a kind•HotTub•Fire Pit• Private•Lux•Charm

*Escape the ordinary and experience rural country luxury *Whether sipping coffee at sunrise or star gazing the Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug and un

4.95 out of 5 average rating, 335 reviews

Cabin in Union Pier

McComb's Cabin, Union Pier, MI

Giant trees welcome you down the drive back to the cabin in the woods. The cabin, along with my house and a small cottage reside on the 2 1/2 acre property. 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 & special days.

Superhost

4.91 out of 5 average rating, 221 reviews

CASA TICA Serenity Amongst Nature Dog Friendly

Come spend your holiday retreat in truely private loft house. Casa Tica has the feel of tree house surrounded by trees, living space on 2nd floor on acre of moss tree lined trails. Sit on your lrg 10x14 deck and listen to the birds sing and gaze from above into the beautiful woods. This is your space to feel alone and amongst nature. Behind your loft look out to the magical woods and enjoy a fire at the bomb fire pit or let the kid loose in you and swing on the architectural swing set.

4.9 out of 5 average rating, 153 reviews

Cottage in Union Pier

Camp Wanderlust-Cozy lodge-20 minute walk to beach

A place to wander with the ones whose company you enjoy. Enjoy a cozy getaway, in our quiet cottage. 10 minute walk from shops and brewery and restaurants of Union Pier. 10 minute walk to Winery Tasting. 20 minute walk to Townline Beach. Union Pier is the perfect beach town in the heart of harbor country, enjoy exploring this magical region or maybe just kick back and build a fire and enjoy the space. 1914 a colony of Chicago bohemians, vacationed at the "Camp's Cottages" at Union Pier.

4.96 out of 5 average rating, 189 reviews

Cabin in Michiana

Steps to the beach at luxury cabin 1hr to Chicago

Book your winter escape to our designer log cabin on Lake Michigan! Just steps from the beach and nestled in a peaceful forest, it's the perfect wintry retreat one hour from Chicago. Built in 1932, our charming cabin sleeps 8 guests in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit with games, puzzles & books. Featured in Country Living and the New York Times, it's perfect for families, friends, or solo retreats. Book now and create lasting memories in this hidden gem!

Tiny home in New Carlisle

4.99 out of 5 average rating, 155 reviews

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country

Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

4.94 out of 5 average rating, 281 reviews

Flat in New Buffalo

Peach by the Beach! 1 Bdrm Apt close to downtown

The Peach by the Beach is a one-bedroom private apartment that sleeps two people. It's a two-minute walk to downtown New Buffalo and a ten-minute walk to the beach! This chic apartment is close to the beach, restaurants, shopping, and all kinds of fun! This location is perfect for couples, singles, and business travelers. It is the perfect getaway from the hustle and bustle of daily life. This location includes free wifi, coffee and tea, beach towels and chairs, and a full-service kitchen.

4.96 out of 5 average rating, 449 reviews

Barn in Michigan City

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!

4.99 out of 5 average rating, 127 reviews

luxe new buffalo lodge, hot tub, 12m walk to beach

Relax with family or friends at our peaceful place to stay. Located in the heart of Union Pier , walking distance to Beach and lots of attractions. Easily will sleep 16 , chill modern lodge vibe to it , high ceilings, heated concrete floors , 2500 sq ft , new construction , 5 bedroom/ 2.5 bath .Set on front porch overlooking forest year round , stroll to patio and enjoy your private hot tub . Home is spacious, 70 ft long so plenty of room to spread out and or host a large gatherings .

Guest house in New Buffalo

4.98 out of 5 average rating, 838 reviews

"Tiny House" Guest House - No Cleaning Fee

"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.

4.97 out of 5 average rating, 150 reviews

Walk to Beach/Dining/Drinks + Patio with Firepit!

Our newly built home is located in the heart of Union Pier - one block to the downtown and a 10 min walk to the closest beach! Stroll out the door for your morning coffee/pastry at Black Currant Bakehouse. Grab your beach rentals at Red Arrow Ride, groceries at Union Pier Market, and unwind with live music at Union Pier Social or a beer at Seedz. Spend a lazy day at the beach or head out to explore the area - there's no limit to amazing breweries, wineries, and restaurants!

4.96 out of 5 average rating, 228 reviews

Home in Lakeside

Couples alert! PVT beach access, hot tub, firepit!

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!

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Popular amenities for Harbor Country holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Harbor Country

4.96 out of 5 average rating, 50 reviews

The Luna Cottages - Unit 3 - Private Beach Access!

WendyRating, 5 stars1 month ago

Me and my pup stayed here for a quick peaceful weekend getaway and it was the best experience we could ever ask for! The place was super clean and just like described and the sunset at the private beach was so beautiful. Alyese was super friendly and helpful and was quick to respond if I ever had questions! I would 100% visit this cute place again with Bruno! 🥹

Superhost

Guest house in New Buffalo

4.86 out of 5 average rating, 21 reviews

Blue Laguna Cottage I Private Beach I Riverfront

TressaRating, 5 stars1 week ago

Very nice home and surrounding area, and very active community. The loft is fun for kids. The host reached out daily. Easy walk to the beach with our dog. The boat rental w/ captain was fun, and got a little tour of the shoreline. Awesome quality of food at the local restaurants!

Luxe

5 out of 5 average rating, 7 reviews

NEW! 1BR Cottage w/ Pool, Firepit, Walk to Beach

KasiRating, 5 stars2 weeks ago

This was a beautiful place to stay. We swam in the pool on a cool day but the pool was heated and very enjoyable. We also enjoyed the hot tub everyday and the walk to the beach was a nice short walk to the end of the paved road. Had a couple questions during our stay and the host reaponded quickly. A nice place to stay this time of year if you’re looking for a place to relax!

Guest house in Valparaiso

4.98 out of 5 average rating, 82 reviews

Lake retreat w/ unique dome near Indiana Dunes

BobbyRating, 5 stars1 week ago

Beautiful stay with a very responsive and helpful host.

4.97 out of 5 average rating, 38 reviews

Home in Michigan City

Birch Nest Cottage by The Lake

MelissaRating, 5 stars5 days ago

We loved staying at Katrina’s place! It was very comfortable, clean and uncluttered. We felt right at home the minute we walked through the door. New Buffalo was a short drive away so had a nice dinner at the Stray Dog. We loved spending time down at the beach and then coming home to grill some steaks. Katrina was very helpful and super communicative during our stay! Thank you for a wonderful weekend away!!

5 out of 5 average rating, 94 reviews

Home in La Porte

UncleLarrysLakePlace HotTubKayaksPingPong

LaniRating, 5 stars3 weeks ago

Jamie's place was the perfect getaway! The view of the lake is beautiful, the house is very clean and we had plenty of space for our family of 7. The ping pong table and games were a great touch. Thank you for a lovely and enjoyable experience!

4.98 out of 5 average rating, 58 reviews

Home in Buchanan

-The District 5 Schoolhouse-

SarunasRating, 5 stars2 weeks ago

We were absolutely impressed by this beautifully designed space. The interior is incredibly tasteful, with a unique character and soul that makes it feel truly special. Everything was spotlessly clean, and every detail was thoughtfully prepared — we had everything we could possibly need during our stay. Highly recommended!