
Cottage holiday rentals in Penn Township
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Top-rated cottage rentals in Penn Township
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Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.
Welcome to the our Lake Retreat "The Toasted Marshmallow" and B&P Getaways where we have 5 unique lake homes in the Sister Lakes area. Please click on my profile picture twice to check them out. We have them in all sizes. Inquire about our private chefs, boat captains, wine tours, yoga instructor, massage therapist, boat rental and concierge services. We will help you make a fun, memorable and enjoyable trip. from a Family trip to your bachelorette party. book today! Inquire before booking
4.98 out of 5 average rating, 109 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.
4.94 out of 5 average rating, 241 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
4.83 out of 5 average rating, 341 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.
4.85 out of 5 average rating, 133 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.
4.9 out of 5 average rating, 258 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 3 bikes! So close to boutiques, coffee shops and cute restaurants!
4.97 out of 5 average rating, 196 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!
4.88 out of 5 average rating, 225 reviews
Lake house in Lawton
Welcome to Bankson Lake! The water/fishing is great and the wineries are nearby! Try our cozy 5 bed, 3.5 bath home complete with amazing waterfront views and a fire pit down by the water; easily sleeps 13+. There’s a newly added bar area in the basement 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!
4.81 out of 5 average rating, 118 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.
4.97 out of 5 average rating, 143 reviews
Romantic 1 BR Lakeside Cottage w/ KING BED
Welcome to our lake-side cottage sitting just a few feet from beautiful Maple Lake. Enjoy your morning coffee or evening wine on the deck while taking in breathtaking views and watching Geese, Swans, Ducks and Blue Herons. In summer enjoy fishing, swimming, kayaking and pedal boating. In winter, ice skating, skiing, tubing, ice-fishing and snowmobiling. Kick back and soak up the slow pace of lake living on roughly one acre of lakefront property at your disposal.
4.99 out of 5 average rating, 101 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.
4.98 out of 5 average rating, 132 reviews
Cozy Riverside Cottage Retreat - SKI TRIP
Welcome to our riverside cottage is perched on a scenic bluff overlooking the river. This cozy space is perfect for nature lovers, outdoor adventurers, and anyone seeking a quiet escape that’s a step above camping. Please note: this is a river cottage, not a resort. NOT SUITABLE FOR CHILDREN River access is a 5-minute walk down the block, great for kayaking, fishing, or just relaxing. Great for unplugging and enjoying nature
4.87 out of 5 average rating, 102 reviewsPopular amenities for cottage rentals in Penn Township
Cottage rentals with a hot tub

Cottage Escape cozy getaway for two, Clean, Quiet
4.94 out of 5 average rating, 600 reviews
Lake View Cottage
4.94 out of 5 average rating, 234 reviews
Cozy Lakefront Tiny Home w/ Hot Tub
4.95 out of 5 average rating, 385 reviews
The Cranny at Michaels Nook
4.91 out of 5 average rating, 133 reviews
Beach Bliss | Pet Friendly W/Hot Tub Near Lake MI
4.82 out of 5 average rating, 213 reviews
The Lemonade Cottage, New Buffalo. Walk to beach!
4.94 out of 5 average rating, 189 reviews
The Dacha • Hot Tub, Family-and-Dog-Friendly House
4.99 out of 5 average rating, 132 reviews
Harbor Country Michigan Hide-Away
4.97 out of 5 average rating, 291 reviewsPet-friendly cottage rentals

Floyd's Cottage in Lakeside, Michi
4.89 out of 5 average rating, 613 reviews
Cottage with Character
4.86 out of 5 average rating, 363 reviews
Camp Wanderlust-Cozy lodge-20 minute walk to beach
4.9 out of 5 average rating, 200 reviews
New Buffalo retreat - Perfect year-round getaway!
4.98 out of 5 average rating, 241 reviews
Sawyer Cottage:New Airbnb Fees;Same Price to Guest
4.9 out of 5 average rating, 475 reviews
"The Pines" in Union Pier: Year-round getaway
4.98 out of 5 average rating, 270 reviews
Cozy Sawyer Beach Cottage- Walk to Warren Dunes
4.9 out of 5 average rating, 281 reviews
Perfect ND Location! Corner of ND Ave & Angela Blv
4.78 out of 5 average rating, 112 reviewsPrivate cottage rentals

Peaceful, relaxing and cozy vintage style cottage
4.94 out of 5 average rating, 129 reviews
Lake Access|Spacious Cottage&Guest House|Sleeps 12
4.94 out of 5 average rating, 277 reviews
Charming Cottage on Beautiful Fish Lake
4.94 out of 5 average rating, 127 reviews
Cozy Farmhouse Near Wineries & Lake Michigan
4.85 out of 5 average rating, 109 reviews
Dune Escape to the Lake Michigan lakeshore!
4.97 out of 5 average rating, 141 reviews
Lakeside Sylvan-Lake Rome City Cottage
4.98 out of 5 average rating, 272 reviews
Cozy. Clean. Convenient.
4.92 out of 5 average rating, 100 reviews
Sunset View Lake Cottage
4.77 out of 5 average rating, 116 reviewsDestinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- Cleveland Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Lexington Holiday rentals
- London Holiday rentals
- Downtown Chicago Holiday rentals
- Warren Dunes State Park
- University of Notre Dame
- Bittersweet Ski Resort
- Silver Beach Carousel
- Potato Creek State Park
- Gun Lake Casino
- New Buffalo Public Beach
- Fenn Valley Vineyards
- South Beach
- Grand Mere State Park
- 12 Corners Vineyards
- Weko Beach
- Van Buren State Park
- Shady Creek Winery
- Jean Klock Park
- Silver Beach Park
- Four Winds Casino
- Four Winds Casino
- Dablon Winery and Vineyards
- Woodlands Course at Whittaker
- Blue Gate Restaurant & Bakery
- Studebaker National Museum
- Four Winds Field
- Howard Park





