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Cottage holiday rentals in Penn Township

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Top-rated cottage rentals in Penn Township

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

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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
4.8 out of 5 average rating, 282 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

Superhost
A private hot tub is visible, featuring a clear water surface and multiple jets. The tub is surrounded by a wooden deck, providing a relaxing outdoor space for guests to unwind.
Cottage in Three Oaks
4.83 out of 5 average rating, 189 reviews

It’s Sauna & Fireplace Season | Hot Tub| Sleeps 9

Wanna Play?? You name the game & we most likely have it! Outdoor fun includes YEAR-ROUND hot tub, Pickleball & Volleyball nets, Soccer goals, Putting Green, corn hole and even cruiser bikes. Indoor fun incl. complete poker table/set & a ton of board games! If you prefer to take it easy you can relax by our indoor fireplace or the outdoor fire pit, recharge in the YEAR-ROUND indoor sauna or stroll to nearby Harbert Beach. Whatever your choice, THIS is the place to experience Harbor Country

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
4.86 out of 5 average rating, 110 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.

Top guest favourite
A cabin-style home is nestled among tall pine trees, featuring a large facade with distinctive tall windows that allow natural light to flood the interior. Colorful chairs are positioned on the screened porch, surrounded by well-maintained greenery and flower beds.
Cottage in Union Pier
4.98 out of 5 average rating, 239 reviews

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

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus additional parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

Superhost
A serene waterfront view is presented, featuring a calm lake with a shimmering surface reflecting sunlight. A wooden deck with seating is situated beside the water, complemented by a fire pit and a small dock extending into the lake.
Cottage in Lawton
4.81 out of 5 average rating, 113 reviews

Lake house in Lawton

Welcome to Bankson Lake! The water/fishing is great and the wineries are nearby! Try our cozy 3 bed, 2.5 bath home complete with amazing waterfront views and a fire pit down by the water; easily sleeps 9+. There are great wineries, breweries, and apple orchards close by and we're only 2 hours from Chicago. There's a row boat, 2 kayaks, and paddle board available. We have min 6 night stay for summer months that is strict unless dates are <3 wks out. Feel free to reach out with any questions!

Guest favourite
A well-maintained single-story home is seen alongside a spacious driveway leading to a two-car garage. The home features a charming front porch and neatly landscaped yard, with green grass surrounding the property and trees lining the background.
Cottage in Benton Harbor
4.89 out of 5 average rating, 228 reviews

Cottage near Hagar Beach Pet friendly with Hot tub

•Brand New Nordic Hot Tub• •September 2023 • Gather with family or meet with friends, there's plenty of room to stay the weekend. The inside of the home has refinished hardwood flooring throughout from the 1930's. The entire home is newly renovated giving it a classic Lake Michigan vibe. Only a few hundred feet from Lake Michigan's shoreline and one mile to pet friendly Hagar Park, there's a playground for the kids and plenty of beach to lay around on and enjoy with family and pet's.

Top guest favourite
Sunlight filters through trees, casting gentle shadows across the lush lawn. A serene lake reflects the sky, with a canoe and dock visible in the distance. A swing set and seating area are positioned to enjoy the tranquil views.
Cottage in Howe
4.95 out of 5 average rating, 711 reviews

Cozy Nest - Lakefront, Dock, Kayaks, Pet Friendly

The Cozy Nest is an adorable three-bedroom, pet-friendly cottage with amazing views of a quiet, no-wake lake. Enjoy the stunning view while your cares melt away in the hot tub. The kitchen is fully stocked and ready for your use. Fiber optic wifi will keep you connected. There are two bicycles available for exploring the surrounding countryside as well as a canoe, 3 kayaks, and paddle boat to use on the water. Shipshewana is a quick 15-mile drive away through beautiful Amish countryside.

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, 242 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.

Top guest favourite
A charming cottage is surrounded by lush green landscaping and vibrant flowers. A screened-in porch is adorned with lights, leading to an inviting entryway. A separate storage garage is visible in the background, complementing the colorful exterior of the cottage.
Cottage in Union Pier
4.94 out of 5 average rating, 370 reviews

Steps to the Beach! Screened in Porch & Firepit!

Experience the ultimate Harbor Country getaway! Just a 90-second stroll to a public beach access and under 5 minutes to another, this location is unbeatable. Spend your day soaking up the sun, kayaking, paddle-boarding, antiquing, golfing, or climbing majestic dunes. Discover endless local breweries, wineries, and top-rated restaurants. Unwind in the evening on the spacious screened-in porch or by the cozy firepit. Your perfect retreat awaits - adventure and relaxation all in one!

Guest favourite
A spacious screened-in porch is adorned with comfortable seating and decorative pillows. Large windows allow natural light to fill the area, while a decorative table at the center holds a selection of refreshments. The serene view of the surrounding landscape enhances the inviting ambiance.
Cottage in Sawyer
4.97 out of 5 average rating, 164 reviews

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

Guest favourite
A tranquil lake scene at sunset is captured, showcasing the water's mirror-like surface reflecting soft hues of pink and orange. Lush trees line the horizon, and hints of clouds add texture to the serene sky.
Cottage in Howe
4.93 out of 5 average rating, 109 reviews

Peaceful, relaxing and cozy vintage style cottage

Nestled in the heart of Amish country, this charming cottage has everything you need for a relaxing getaway at the lake. Vintage style cottage features a private back yard with a fire pit, deck with a picnic table and grill for your enjoyment. Free firewood, two kayaks and canoe for boating on the no wake lake. The property is located across the street from the lake, it includes lake access and a shared pier. Visit Shipshewana and enjoy all this quaint small town has to offer.

Popular amenities for cottage rentals in Penn Township

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