
Cottage holiday rentals in Penn Township
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Penn Township
Guests agree: These cottages are highly rated for location, cleanliness and more.

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

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.

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.

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.

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.

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!

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.

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!

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.

J’s Beach House: Hot Tub & short walk to beach!
J's Beach House is < a 5 minute walk to the beach! My cottage is equipped with a private hot tub and fireplace. Enjoy the walkable town or jump in your car for a quick drive to any Harbor Country activity! Potential for rental with adjacent cottage "Riley's Retreat". *Please inquire about our other Airbnb cottage near downtown Union Pier. This cottage is a 2-bedroom plus kids loft, screen porch, hot tub, fire pit, plus walking distance to Townline Beach!

Quaint Cottage: guests rave clean; cozy; quality
This charming, semi-private cottage, set in a quiet country location is perfect for your next getaway. Small kitchenette with sink, fridge and microwave provides you with kitchen basics. PLEASE NOTE: there is no stove/oven in this room. Bathroom is equipped with all the necessities plus extras like a two person shower with rain fall shower head. Outside is a 2-3 person hot tub along with a beautiful pergola with string lights and adirondack chairs.

Stone Cottage on Kerr Island
Welcome to the little stone cottage on beautiful Sylvan Lake. We are located in Rome City, IN. This adorable house, originally built in 1930, was remodeled and completely renovated in 2018. The updated kitchen features tiled backsplash, gas range, oven, and fridge. There is a microwave and Keurig for your convenience. The bedroom has a queen-sized bed, a small wardrobe for hanging clothes, and a dresser. The bathroom features a tiled shower.
Popular amenities for Penn Township cottage rentals
Cottage rentals with a hot tub

The Cottage of Harbor Country - Close to it all!

The Lemonade Cottage, New Buffalo. Walk to beach!

Harbor Country Michigan Hide-Away

Beach Bliss | Pet Friendly W/Hot Tub Near Lake MI

Cozy Lakefront Tiny Home w/ Hot Tub

Hot tub! Red Tin Cottage of Harbor Country!

Designer Cottage Relax Pool Beach & Spa—Windjammer

Hot tub open year round in modern/rustic cottage!
Pet-friendly cottage rentals

Northwind Llama retreat “Chicken coop”

Bright & Warm by Warren Dunes Maple St Beach House

Lakeside Getaway

The Koi Cottage - Union Pier- Dog Friendly!

New Buffalo retreat - Perfect year-round getaway!

Cedar Lake Knotty Cottage Pontoon for Rent 2025

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

Camp Wanderlust-Cozy lodge-20 minute walk to beach
Private cottage rentals

South Haven Casa Azul

Cozy. Clean. Great for couples & small families

Barron Lake front Cottage. Notre Dame Nearby!

Green Acres

Cozy little cottage

Sunset View Lake Cottage

Charming, stylish, lake home w/pool

Best sunsets from new covered deck
Destinations to explore
- Chicago Holiday rentals
- Northeast Ohio Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Southern Indiana Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Cleveland Holiday rentals
- Cincinnati Holiday rentals
- London Holiday rentals
- Warren Dunes State Park
- University of Notre Dame
- Bittersweet Ski Resort
- Silver Beach Carousel
- Potato Creek State Park
- Woodlands Course at Whittaker
- Fenn Valley Vineyards
- Gilmore Car Museum
- Four Winds Casino
- Tiscornia Park
- Potawatomi Zoo
- New Buffalo Public Beach
- Four Winds Casino
- Dablon Winery and Vineyards
- Grand Mere State Park
- Silver Beach Park
- 12 Corners Vineyards
- Shady Creek Winery
- Studebaker National Museum
- Morris Performing Arts Center
- Four Winds Field
- Blue Gate Restaurant & Bakery
- Benton Harbor St Joseph Ymca
- Jean Klock Park




