Cottage holiday rentals in Penn Township

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Top-rated cottage rentals in Penn Township

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Guest favourite

A cozy living area features a gray sofa adorned with patterned cushions, complemented by a pair of leather chairs. Natural light floods through large windows, illuminating the hardwood floor. A coffee table sits at the center, while a flat-screen TV is mounted on the wall.

Cottage in Sawyer

4.93 out of 5 average rating, 228 reviews

Bright & Warm by Warren Dunes Maple St Beach House

Beautiful renovated house on wooded lot, half mile to the Warren Dunes! Home completely designed for the ultimate vacation rental getaway! SS kitchen, memory foam mattresses, marble bathrooms w/walk-in shower on main floor & full bath w/tub up, hardwood floors, gas fireplace in sitting area and great room that connects the living/dining and kitchen. Roast s’mores, grill steaks & sip local brews in the private backyard w/ fire pit. Central to everything in Harbor Country. Come enjoy winter w/us!

Top guest favourite

A cozy living room is featured with a soft beige sofa and an armchair in navy blue. A light rug with earthy tones is placed under a white coffee table, which holds magazines. A fireplace is surrounded by decorative mirrors, enhancing the welcoming environment.

Cottage in Stevensville

4.93 out of 5 average rating, 201 reviews

Cheerful Stevensville cottage, GREAT LOCATION!

Right in the prettiest area of Stevensville, Glenlord Cottage is an ideal location for your Southwest Michigan stay. Down the road you will find Glenlord Beach Park, a beautiful Lake Michigan overlook. Around the corner, an award-winning bakery. In Stevensville with its variety of restaurants, beaches, and shops, Glenlord Cottage is also within easy reach of many SW Michigan attractions and is well placed for visits to wineries, golf courses, and downtown St. Joseph with its shops and festivals.

Top guest favourite

A spacious living area features large French doors that open to a deck. A neutral-toned sofa is adorned with decorative pillows, while a wooden coffee table sits in front. An inviting armchair and framed artwork complement the warm, natural lighting filtering in.

Cottage in Sawyer

4.99 out of 5 average rating, 108 reviews

The Cottage of Harbor Country - Close to it all!

Welcome to your very own Cottage in Harbor Country! The perfect weekend getaway from Chicago, our cottage is close to Warren Dunes and just a 15-20 minute walk to Lake Michigan. Renovated and beautifully appointed, it blends vintage charm with modern updates! Enjoy morning coffee on the new deck or screened-in porch, take a dip in the new hot tub, or cozy up next to the wood-burning fireplace. Enjoy the perfect place to relax, hike, go antiquing, wine-tasting, and make memories with loved ones!

Top guest favourite

A cozy cottage is depicted, featuring a welcoming front deck with seating under a shade structure. Stairs lead from the yard to the entrance. Lush greenery frames the property, and the nearby rocky pathway provides access to the water, enhancing the outdoor space.

Cottage in Middlebury

4.81 out of 5 average rating, 289 reviews

Stone Lake Cottage Middlebury IN Boat Fish getaway

Located on beautiful Stone lake in Middlebury, IN. Crafts Amish antique auction fish swim lake relaxing. Bedding, towels, and personals/toiletries are provided. 2 queens, 1 twin, 2 double beds. Includes 3 BR/4 baths (detached 3rd BR CLOSED in winter), room for 6-8, AC, Smart TV, streaming services , WiFi, fireplace, lake, pier, kayak, paddle boat, grill, fire pit, dishwasher, toys for swimming, fishing, and 5 miles from Shipshewana/Middlebury. Min primary guest age is 21. Motel hotel

Guest favourite

A cozy sleeping area features a spacious bed with a soft, textured throw blanket draped over it. An antique world map hangs above the bed, complemented by warm pendant lights. A decorative pillow adds an inviting touch to the arrangement.

Cottage in Dowagiac

4.87 out of 5 average rating, 113 reviews

Vintage Romance Finds Cozy Charm at Depot Cottage

Convenience and luxury combine in this imaginative and engaging Cottage just steps away from the Historic Train Station in this Charming All-American town. Our Vintage Travel/Train themed Cottage has family friendly features, like a children's train playroom, working model trains, stocked kitchen, and a spacious enclosed backyard for four legged babies. With romantic features like a beautiful vintage soaking tub and 100% linen bedsheets we fit any vacation requirement. Walkable to all needs.

Guest favourite

A quaint cottage features a pink façade with a covered porch supported by white columns. Lush greenery surrounds the property, with large trees providing shade and a well-maintained garden visible in front. Barn-like structures are seen in the background.

Cottage in Topeka

4.9 out of 5 average rating, 186 reviews

Honeyville Cottage

Escape from the hustle of daily life in the heart of Amish country. Step into this quaint cottage and leave your worries at the door. Soak your cares away in the cast iron claw foot tub or relax on the patio watching the neighbors horses run. Bicycles are available for a stroll through back country roads. Play games around the kitchen table. Take a trip into town for fresh baked Amish goods, a traditional Amish dinner or shopping. At night you can grab a blanket and lay under the stars.

Top guest favourite

A welcoming entry features a set of stairs leading up to the cottage, flanked by white railings. A decorative American flag is displayed on the front porch, surrounded by landscaped areas with pebbled ground and greenery.

Cottage in Rome City

4.98 out of 5 average rating, 247 reviews

Lakeside Sylvan-Lake Rome City Cottage

Welcome to Sylvan Lake in Rome City, IN. Sylvan Lake is an all season ski lake wonderful for all boating, fishing, skiing, tubing, wave runners and even a swim from the dock. You have 60 feet of lake front with two docks to bring your lake toys or rent a pontoon for the day/weekend or week. Full size kitchen, laundry, two big smart tv's with cable and wifi. Small shed for storage, large deck, canoe for 3, fire pit & gas grill. Wedding, family, golfing or weekend away? Lakeside Sylvan!

Superhost

The exterior of the cottage is shown, featuring a yellow siding with large windows that provide ample natural light. A small wooden deck is visible in front, furnished with a grill and seating. Well-maintained green shrubs and grass surround the property.

Cottage in Decatur

4.88 out of 5 average rating, 132 reviews

Charming Cottage on the Lake

This charming family cottage on beautiful Lake of the Woods is a perfect, Pure Michigan getaway — summer, fall, winter or spring. With bright, light-filled rooms, original hardwood floors and updated bedrooms and bath, all views point to the beautiful lakefront with 180-degree views. Enjoy the hot tub in the cooler months or the shared pier and swimming in the warmer months. No matter how you spend your time here, you will leave refreshed and recharged at this peaceful family respite.

The exterior of a modern home is displayed at dusk, featuring a well-maintained facade with soft lighting. An American flag is prominently displayed by the entrance. Surrounding grass is trimmed, and a peaceful wooded area is visible in the background.

Cottage in Coloma

4.8 out of 5 average rating, 163 reviews

Just 1 Mile to Lake Michigan

leisurely mile from 🐩 friendly Lake Michigan beach, HOT TUB 🥵 AVAILABLE! our stylish home offers a perfect blend of comfort and charm. 3 bedrooms, 1 bath, charcoal grill, picnic table and Wi-Fi. Unwind in the hot tub on crisp evenings under starlit skies. Explore local wineries, parks, lakes, and quaint shops, or dine at nearby restaurants. Relax on the stunning beaches and enjoy the tranquility of our quiet country setting. 15 minutes from St. Joseph and 18 from South Haven.

Guest favourite

An outdoor area is shown featuring a hot tub positioned on a wooden deck. The red exterior of the cottage contrasts with the surrounding green grass and wooden fencing. A glass door leads into the main structure, enhancing the inviting rural charm.

Cottage in Benton Harbor

4.86 out of 5 average rating, 197 reviews

Hot tub! Red Tin Cottage of Harbor Country!

Welcome to The Red Tin Cottage of Harbor Country! Nestled in a quiet, rural setting Red Tin is a character-filled, country-chic escape in beautiful Southwest Michigan. Within minutes of award winning beaches, golf courses, wineries, breweries, and restaurants you can be close to it all and retreat back to peace. Take a dip in the hot tub on a starry night, relax in the claw foot tub after a day of play, or enjoy stories around the firepit with family and friends. Come gather!

Guest favourite

A cozy living area features a fabric sectional sofa with colorful cushions and a knit throw. Natural light streams through large windows with gray curtains, complementing the soft carpet flooring. A vintage wooden coat rack stands nearby, adding functional charm.

Cottage in Sawyer

4.84 out of 5 average rating, 157 reviews

Wineries Breweries Warren Dunes Lake Michigan WOW!

Located just outside of Bridgman, this Lake Township home is clean, quaint and accessible to so many great things that are offered in Southwest Michigan—-15 wineries within a ten mile radius, many breweries including Transient and Haymarket in Bridgman, great restaurants, Weko Beach and Warren Dunes State Park! The home offers a perfect place to wind down after a day on the beach or at the wineries—with countless options for amazing food for any meal—or you can cook at home

Guest favourite

A spacious cottage is surrounded by tall trees, offering shade and a relaxing environment. A large deck extends from the back, while a fire pit area with Adirondack chairs sits on the grassy lawn, inviting outdoor gatherings.

Cottage in Dowagiac

4.96 out of 5 average rating, 131 reviews

The Wildwood Cottage, private lake access

New for summer 2023, private lake access across the street on Little Crooked Lake! Peaceful, 2-bedroom cottage in the heart of Sister Lakes, Michigan. Fully renovated in 2021, this cottage features a large deck overlooking trees and a partial view of Little Crooked Lake. Eat-in kitchen, Weber charcoal grill, Adirondack chairs, and patio dining for 6. Walking distance to The Strand and Sister Lakes Brewing Company. 17 miles to Lake Michigan and 30 miles to Notre Dame.