House holiday rentals in Benton Harbor

4.97 out of 5 average rating, 125 reviews

A bright living area is furnished with a green velvet sofa and a wooden coffee table, complemented by two yellow chairs. Large windows allow natural light to fill the space, highlighting the dark hardwood flooring and decorative plants.

Home in Stevensville

Lavish Lakeside Historic Downtown Home-Beach 1.5mi

This historic 2,000 sqft home will surely impress with its undeniable charm, character, comfort & convenient location. Walk across the street to Watermark Brewing, Red Coach Donuts, or The Solarium. 4 person arcade with 100's of games. High-speed WiFi with ALL streaming platforms. Full laundry & kitchen with everything you need to feed an army. Sip coffee on the porch swing or catch up around the fire pit. Relax after a long day at the beach/winery. Spacious private yard with parking galore.

4.98 out of 5 average rating, 307 reviews

A spacious living area showcases a light-colored sectional sofa adorned with plush pillows. Large windows allow natural light to fill the room, revealing wooden flooring and eye-catching artwork on the walls. A dining table is visible in the background, complemented by a minimalist plant.

Home in Michigan City

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

A two-story cabin exhibits a charming exterior with dark blue siding and white trim. A spacious deck wraps around the upper level, leading down to a well-kept grassy yard. Steps are visible, framed by mature trees, providing a peaceful outdoor environment.

4.99 out of 5 average rating, 135 reviews

Hot tub & sauna, pet friendly, 1/2m to Hagar Beach

Peaceful, newly renovated 1930’s cabin walkable (1/2 mile) to Hagar Beach in the heart of SWMI. This pet-friendly home has a cozy feel with an outdoor hot tub, sauna, & fully-furnished spaces perfect for a relaxing getaway, remote work, or staycation home base while you explore the lake, bike trails, breweries, & eateries. Enjoy a quiet, off-the-beaten path stay close to everything Lake Michigan offers featuring a stocked kitchen, cozy reading nook & desk, and outdoor dining & fire pit.

4.93 out of 5 average rating, 137 reviews

A welcoming front porch features four white columns and decorative pots with greenery. Two seating areas are provided: a pair of black rockers on one side and a cozy seating arrangement on the other. A patterned mat enhances the entrance's appeal.

Home in Berrien Springs

Entire House in Berrien Springs

In the heart of Berrien Springs! Walking distance to the local library, downtown for restaurants & shops, and only 1 mile from Andrews University. Great location within a 30-minute drive; Notre Dame, Warren Dunes State Park, downtown St Joseph, Harbor Shores Golf Club, and many local wineries and farmers' markets. Pet-friendly, just make sure to ADD the pet fee when booking. This is a NO SMOKING property, which includes inside and outside the property too. Please read the house rules.

An elegantly designed outdoor gazebo is illuminated with string lights, creating a cozy atmosphere. A round firepit sits at its center, surrounded by a mix of wicker seating. A patterned rug adds texture to the wooden deck, surrounded by trees in the background.

4.97 out of 5 average rating, 129 reviews

A Home with a Forest Scent and the Sound of Waves

Escape to Pure Michigan! This charming home is a short walk to Hagar Beach and just a quick 10-minute drive to Silver Beach. Love golf? Tee off at Harbor Shores, Lake Michigan Hills, or Paw Paw Lake Golf Club. Sip and savor at Contessa Wine Cellars and Filkins Vineyards, or pick fresh fruit at Jollay Orchards and Fruit Acres Farm—all just a short 15-minute drive or less! After a day of adventure, relax by the cozy outdoor fireplace—the patio glows beautifully at night with string lights.

4.98 out of 5 average rating, 157 reviews

The exterior view showcases a modern lodge-style home with dark wood paneling and large windows. A pathway leads toward the entrance, bordered by greenery. Soft lights illuminate the building, creating a warm ambiance against a backdrop of trees.

Home in Union Pier

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 .

4.87 out of 5 average rating, 183 reviews

The cottage features a welcoming facade with blue shutters and a vibrant red front door. A decorative flag is displayed on the porch railing, surrounded by neatly manicured greenery and blooming flowers, contributing to the inviting outdoor space.

Home in Stevensville

Cheerful 3BR 2BA Country Cottage Near Attractions

Your family will be close to everything when you stay at this centrally-located place. We have sought to equip our home to a high standard and to anticipate your needs by providing all the things you might want for a relaxing stay. There are games in the back yard that will interest all ages. Close to beaches, wineries, Four Winds Casino, cross country ski, South Bend football, South Haven and many other locations. We also provide a pass to Silver Beach and all other county parks.

4.98 out of 5 average rating, 232 reviews

An inviting hot tub is positioned outdoors, surrounded by lush greenery. A wooden privacy screen adds to the tranquility, while an outdoor shower with modern fixtures is nearby. The patio area is designed for relaxation, creating a soothing space for unwinding.

Home in South Haven

Hot Tub & Private Beach Access | Family Friendly

5 min walk to Private Beach 10 min drive to Downtown South Haven 18 min drive to Downtown Saugatuck This beautiful 3 bedroom home in an exclusive community is the perfect getaway for family or friends. You can bask in your own little piece of paradise on Lake Michigan’s beautiful coastline. Every room is designed for luxury & comfort. It’s just minutes from the beach and downtown attractions - shops, restaurants, and nightlife. Experience South Haven With Us & Learn More Below!

A year-round hot tub is set against a backdrop of lush greenery, with gentle water jets creating a soothing ambiance. String lights cast a warm glow above, complementing the evening sky as it transitions to dusk. Comfortable seating is arranged nearby for relaxation.

4.97 out of 5 average rating, 181 reviews

Lake MI views: King bed: Mins to St. Joe: Hot tub

🤩 Spectacular Lake Michigan views 🌅 Deck overlooking Lake Michigan 🔥 Year-round hot tub 📍 Minutes to downtown St. Joe ✨ Magical fire pit space 🏖️ 5 Lake Michigan beaches within 5 miles 🌞 Beach necessitates included 🍷 Close to The Lakeshore Wine Trail 🏓 Ping pong table ⭐️ Top rated home in St. Joe ⛳️ Near Harbor Shores Golf Course 🧑‍🍳 Fully stocked kitchen ☕️ Keurig Duo w/ complementary k-cups ⚡️ High speed internet 👶 Highchair & portable crib 🧺 Washer & dryer

The outdoor hot tub is positioned on a wooden deck, surrounded by lush greenery and tall trees. It overlooks the serene waters of Lake Michigan, providing a tranquil view of the shoreline and sky.

4.98 out of 5 average rating, 125 reviews

Lake Michigan•Private Beach•Amazing View•Hot Tub

Welcome to Spyglass! If you are looking for a perfect place for that a visit to Lake Michigan any time of year, then The Spyglass has you coved. Whether you’re there for couple's retreat, family vacation or girlfriend’s weekend this gorgeous Lake front property with private beach has it all. Being located not too far off the beaten path, only 5 minuets to downtown St. Joseph the Spyglass is a perfect landing zone for all the nearby activities Southwest Michigan has to offer.

A ranch-style house is presented, featuring a welcoming front porch with two chairs. Colorful flowerpots and vibrant blooms adorn the entrance, complemented by a neat lawn. The exterior showcases a blend of subtle hues, highlighting the inviting atmosphere of the home.

4.87 out of 5 average rating, 124 reviews

2 mins from beach/monthly stays available

1200 sq ft ranch style house w 2 bedrooms, 1 bath. Main bedroom has 1 queen size bed, 2nd bedroom has twin size bunk beds w twin size rollaway bed which enables a total of 5 guests. Appliances available for use are stackable washer/dryer, fridge, stove, over the range microwave, and dishwasher. Newer propane grill is available for use. *bunk bed will be difficult for older individuals due to lower bunk being low.

A single-story house is presented with a gray exterior and white trim. A welcoming front porch features seating and flower arrangements. The surrounding property is characterized by a large grassy area and trees, creating a peaceful setting.

4.92 out of 5 average rating, 232 reviews

The QT

Cozy country retreat. Whether you are visiting to explore Lake Michigan beaches (15 minutes away), the Lake Michigan Shore Wine Trail, the Makers Trail, or if you are invited to a wedding at the Blue Dress Barn (5 minute walk) or Sundance Studios (1 mile) this is the place for you! Fall asleep under the stars (skylight) in our brand new king size bed and wake up to a cup of coffee in a cheerful kitchen.

Popular amenities for house rentals in Benton Harbor

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 115 reviews

The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.

Home in Michigan City

Beautiful home with Beach views in Beachwalk

4.83 out of 5 average rating, 185 reviews

A secluded in-ground pool is surrounded by lush greenery and landscaped gardens. Several lounge chairs are arranged near the pool, which reflects the sky above. Flowering plants and shrubs frame the scene, creating a peaceful outdoor retreat.

Home in South Haven

Experience Nature-Charming Cottage

4.96 out of 5 average rating, 184 reviews

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

Home in Michigan City

5 Bedroom Luxury Home In Heart of Beachwalk Resort

4.94 out of 5 average rating, 165 reviews

A private hot tub is set in a wooden enclosure, surrounded by a serene natural landscape. Steps lead up to the hot tub, offering easy access. Two white Adirondack chairs are positioned nearby, inviting relaxation in the peaceful outdoor setting.

Home in Union Pier

Winter & Holiday Couples getaway Pvt Hot tub

4.88 out of 5 average rating, 135 reviews

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

Harbor Country Charm w Heated Pool Open Til 10/12!

4.91 out of 5 average rating, 309 reviews

A game room features a multi-game table for pool, air hockey, and ping pong, surrounded by comfortable bean bag seating. Bright, geometric lighting enhances the space, while classic arcade machines and a large wall Connect 4 game add fun to the cozy environment.

Home in South Bend

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar

4.97 out of 5 average rating, 228 reviews

A modern ranch-style home is surrounded by lush greenery and manicured landscaping. The exterior features a combination of grey siding and a welcoming front porch. A paved driveway leads to the entrance, framed by trees and shrubs, creating a serene wooded environment.

Home in Fennville

FennWoods - A Modern, Wooded Retreat

4.97 out of 5 average rating, 104 reviews

An enclosed indoor pool area features a large, clear swimming pool surrounded by spacious tile flooring. Illuminated by natural light from the ceiling, several lounge chairs are positioned at the poolside, providing a relaxing atmosphere for guests.

Home in South Haven

The Northern Anchor: Your Perfect Getaway!

Weekly house rentals

A bright living area features a patterned rug beneath a round coffee table, surrounded by a floral sofa and two striped armchairs. Large windows allow natural light, while a ceiling fan adds comfort. The adjoining kitchen and dining space are visible, enhancing the open layout.

4.99 out of 5 average rating, 68 reviews

N Shore Bungalow-close to beaches, wineries, golf

A collection of images showcases the exterior of the boutique cottages, featuring a charming light blue cottage with a welcoming yellow door. A pergola adorned with greenery stands in the foreground, while the surroundings include pathways and vibrant flowerpots. The peaceful setting near Paw Paw Lake is emphasized.

4.83 out of 5 average rating, 40 reviews

HeronsNest Boutique Cottage Paw Paw - Lake Access

A cozy living room area is displayed, featuring a gray sofa and two chairs with light-colored cushions and floral patterns. A tall standing lamp illuminates the space beside a leafy plant, while sunlight streams in through nearby windows, creating a bright and inviting ambiance.

5 out of 5 average rating, 27 reviews

Renovated Home 1 Minute to Lake

4.97 out of 5 average rating, 90 reviews

Home in Buchanan

-The District 5 Schoolhouse-

The exterior of a two-story home is framed by well-maintained landscaping. A welcoming porch, complete with steps leading to the front door, is supported by white railing. Adjacent seating areas are visible on the porch and in the yard, surrounded by small trees.

4.97 out of 5 average rating, 38 reviews

Welcome to the Shore Thing!

An updated kitchen is featured, showcasing a central island with seating for four. Light blue cabinetry complements stainless steel appliances, including a microwave and stove. A neutral countertop extends across the kitchen area, and light enters through multiple windows, illuminating the space.

5 out of 5 average rating, 27 reviews

The Delaware

A barrel sauna and a wood-fired barrel hot tub are set in a grassy area surrounded by trees. The sauna features a rounded wooden exterior and is positioned on a circular stone pad, while the hot tub is crafted from wood and located a few steps away.

4.96 out of 5 average rating, 27 reviews

Beach Cottage - Sauna - Hot tub - Fireplace - Wine

A sunlit corner of the room features two brown armchairs positioned beside a round, woven area rug. A small table with a plant rests between the chairs, and large windows provide views of the lush greenery outside. A wood stove is located on one side of the room.

5 out of 5 average rating, 26 reviews

Lagom Lakehouse

Private house rentals

A comfortable gray sofa is positioned against a soft blue wall, adorned with four decorative pillows. A rustic wooden coffee table sits in front, featuring a round basket with seasonal decor and a remote control, while two framed black-and-white photographs hang above.

4.83 out of 5 average rating, 94 reviews

Nestled in History

5 out of 5 average rating, 26 reviews

A cozy fire pit surrounded by dark wooden Adirondack chairs is set on a stone patio. Behind the fire pit, a barrel sauna stands among the trees, offering a rustic touch to the serene outdoor space.

Home in Covert

Hot Tub | Sauna | Walk 2 Lake | Firepit | Wet Bar

5 out of 5 average rating, 94 reviews

A charming cottage sits nestled among trees, featuring light green siding and a welcoming front porch. A gravel pathway leads to the entrance, with a detached garage visible to the left, all surrounded by lush greenery.

Home in Stevensville

Secluded Lake Escape w/ Hot Tub!

5 out of 5 average rating, 18 reviews

24 Acre Secluded Retreat Heated Pool Hot Tub Pond

A two-story house is set against a backdrop of lush green trees. The front porch features white railings and a shaded entry, while the light-colored siding complements the metal roof. Vibrant shrubs and small trees surround the yard, creating a welcoming outdoor space.

4.94 out of 5 average rating, 53 reviews

Beachwood Haven at Harbor Shores

A colorful bedroom features a spacious bed with a striped blanket and decorative pillows. A bedside table holds a lamp, while a ceiling fan provides ventilation. Natural light enters through a window, dressed with dark curtains, creating a cozy ambiance.

4.89 out of 5 average rating, 54 reviews

Getaway Lakeside Cottage-Dog Friendly

A single-story home is presented with a light grey exterior and a welcoming front porch. A well-maintained lawn surrounds the property, complemented by tall trees and shrubbery. A driveway leads to a garage on the right side, contributing to a tidy appearance.

4.94 out of 5 average rating, 31 reviews

Peaceful Retro Retreat

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and an oven. Light cabinetry complements dark countertops, and ample natural light filters through multiple windows, creating a bright cooking space. A microwave is positioned on the counter for convenience.