Cottage holiday rentals in Penn Township

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Top-rated cottage rentals in Penn Township

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Guest favourite

Cottage in Middlebury

4.8 out of 5 average rating, 267 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

Cottage in Three Oaks

4.93 out of 5 average rating, 167 reviews

The Happy Cozy-Pets Welcome, Fire Pit, Privacy

If relaxing in nature in a calm and cozy home is what you're seeking, you'll find it here! It's been designed to make you feel at peace and comfortable inside while providing several outdoor spaces for you to enjoy the sights, sounds, and smells of nature. The open floor plan and large dining table create a grand gathering space for everybody to be together and create the memories that matter most. Feel free to safely start a campfire outside or in the fireplace indoors. It's all here for you!

Superhost

Cottage in Dowagiac

4.86 out of 5 average rating, 105 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.

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Cottage in Lawton

4.81 out of 5 average rating, 112 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

Cottage in Howe

4.95 out of 5 average rating, 682 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

Cottage in Wawaka

4.94 out of 5 average rating, 352 reviews

Cozy Lakefront Tiny Home w/ Hot Tub

Included in your stay are: 2 kayaks 2 paddle boards Hot tub - available year round Paddle boat Fishing poles Gas grill w/ propane Fire pit Private dock Pickle ball paddles/balls for Martin Kenney Memorial Park *See amenities section for complete list. This cottage rests on the shores of Diamond Lake in Wawaka, IN. The lake is a quiet 10 mph lake perfect for fishing, kayaking, swimming or just enjoying time away. Come enjoy this relaxing retreat with great views and a cozy atmosphere.

Superhost

Cottage in Decatur

4.87 out of 5 average rating, 126 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.

Guest favourite

Cottage in Harbert

4.97 out of 5 average rating, 153 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

Cottage in Dowagiac

4.96 out of 5 average rating, 124 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.

Superhost

Cottage in Benton Harbor

4.93 out of 5 average rating, 106 reviews

Lake Bluff cottage, Unforgettable view and sunsets

We have recently renovated and brought this charming cottage, located less than 10 mins to the heart of St. Joes, back to life! It is perched atop a beautiful bluff, high above the Lake Michigan shores- highlighting expansive views and stunning sunsets. Come stargaze with us (starting this spring) at our wonderful Lake Michigan Cottage. Bring your fur baby to enjoy the getaway! ($150 pet fee) 5 night minimum for Holiday weeks (Thanksgiving, Christmas, 4th of July)

Top guest favourite

Cottage in Niles

4.97 out of 5 average rating, 116 reviews

Lake House 11 miles from Notre Dame

This ranch style with walkout is located on beautiful Barron Lake just 11 miles from Notre Dame. Our home has been recently renovated, perfect for entertaining. There are two fully furnished levels including 3 bedrooms, 2 baths, 2 Family Rooms, and 3 indoor eating spaces. Enjoy the sandy beach and lake for fishing and water sports. Patio has tables, chairs & loungers. By reserving and staying at this property you assume all risk for yourself and your guests.

Top guest favourite

Cottage in Paw Paw

4.95 out of 5 average rating, 147 reviews

Water's Edge Escape

Charming 1940’s lakeside cottage is cozy, updated & bright! Fish, swim, kayak or paddle board in spring fed waters. Our humble home has just enough room for you to steal away with those you love. Relax with two bedrooms and a sleeper sofa. Enjoy your morning coffee on the deck overlooking the lake, you may even catch a glimpse of a swan family or Blue Heron. Enjoy seasonal fruit farms, local wineries/breweries or explore nearby St. Joseph or South Haven!