Holiday rentals in Pennville

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Top-rated holiday rentals in Pennville

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Guest favourite

Home in Upland

5.0 out of 5 average rating, 190 reviews

Brick House Upland

Intentionally designed for short term stays, Brick House Upland is set to welcome you to Upland for your visit to Taylor University, Ivanhoes, Upland, or all that Grant County has to offer. With comfort a hotel cannot offer, we hope this welcoming space will allow you to relax and connect with your family and friends. Rates for most nights begin at $95 and increase for select and premium weekends. Use the search bar at the top of the page to start booking now. *Please note: Most weekends require a two night minimum

6–13 Feb

$155 SGD per night

Guest favourite

Home in Huntington

4.97 out of 5 average rating, 376 reviews

⭐A Hidden Gem⭐ King Bed, Hot Tub, Couples Getaway!

-YEAR ROUND Hot Tub w/ privacy fence (yes, it's *that* private) - King Size Bed -Queen pullout sofa bed (living room) -100 MBPS Internet -Two TVs w/ Netflix, Hulu, & more -630 sqft apt/guest house -Washer/dryer -Off St. parking -Fully equipped kitchen -Extra blankets, towels, pillows, etc Also: -10 min to Huntington Reservoir - walking trails, gun range, fishing, etc -10 min from Two EEs winery -20 min to Hanging Rock & waterfalls at Kokiwanee Nature Preserve -See our GUIDEBOOK for much more!

7–14 Oct

$159 SGD per night

Guest favourite

Barn in North Manchester

4.98 out of 5 average rating, 178 reviews

The Shed Retreat

The Shed Retreat is a sacred space for anyone looking to shed their worries, fears, and busy schedules. Once a home for goats located in a secluded area on our property, it is now a peaceful garden oasis among the trees for those seeking a break from the norm. Inside, you can enjoy a cozy and relaxing place to lounge or rest. Outside, you can spend time around the fire pit, collect fresh eggs for breakfast, kayak on a nearby river, bike to local ice cream shops, or take a nap in a hammock.

7–14 Jan

$80 SGD per night

Guest favourite

Home in Upland

4.96 out of 5 average rating, 194 reviews

Quiet, cozy home near Taylor U and Ivanhoe’s

Have the entire home and spacious yard to yourself and be just steps from Taylor University. We are just off of I-69 in the quiet town of Upland, home of famous IVANHOE’S restaurant. This fun and cheerful 1930's home will bring a smile to your face every time you walk in. Main bedroom and both baths on main floor. Spread out in the living room, dining room, eat-in kitchen and back deck. WIFI, Roku, YouTubeTV, fully stocked kitchen and laundry are for your use! Christmas stay? Send inquiry.

15–22 Jul

$143 SGD per night

Guest favourite

Guest suite in Muncie

4.97 out of 5 average rating, 220 reviews

The Eagles Nest, two bedroom retreat.

Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

29 Dec – 5 Jan

$104 SGD per night

Guest favourite

Guest house in Versailles

4.97 out of 5 average rating, 176 reviews

French B&B - Lower Level Apt w/ 2 bedrooms

The French Bed & Breakfast is nestled in the charming town of Frenchtown, Ohio. This B&B has been operating since 1999 and has accommodated many guests coming to visit Darke County. Lower level of our house - it has spacious and quaint accommodations for a reasonable rate. Included: Continental Breakfast, kitchen, great room & patio. Guest rooms on lower level: 2 bedrooms - can be rented individually or as a 2 bdrm apartment (pricing varies based on events - min $75 ea bdrm).

20–27 Jan

$158 SGD per night

Guest favourite

Guest house in Muncie

4.99 out of 5 average rating, 149 reviews

Burlingwood Guest House

You will feel a welcome peace when you enter the private wooded 6 acre property off of Burlington Drive. In a peaceful country setting just south of Muncie you'll enjoy our cozy and comfortable Guest House on this historic property. The setting includes a spacious patio, perfect for enjoying a cup of coffee surrounded by nature. Burlingwood is less than 10 minutes from Prairie Creek Reservoir, the Red Tail Nature Preserve, biking trails, and downtown Muncie.

24–31 Dec

$118 SGD per night

Guest favourite

Home in Muncie

4.99 out of 5 average rating, 138 reviews

The BALL House

Completely remodeled 2 bedroom home near Ball State University. Walk to events, classes & activities. Comfortable furnishings, plenty of natural light. Living room, kitchen is fully equipped with all the necessary appliances and cookware for preparing meals at home. Comfortable bedrooms, backyard with patio. Easy access to public transportation & local shops/restaurants. Perfect for families or friends visiting the University. Have a Ball in the BALL house.

25 Jun – 2 Jul

$140 SGD per night

Guest favourite

Flat in Fairmount

4.96 out of 5 average rating, 155 reviews

Enjoy Nostalgia In James Dean's Hometown

The Rebel Lodge is a fully restored historic brick building located in the heart of James Dean's hometown. Only a short walk to The Fairmount Historical Museum, and right around the corner from Main street. The building will sleep 4-5 with a comfy double bed, a pull out sofa and an additional sofa. It is decorated with fun mid century furniture and decor. Everything is freshly up to date with new furnace, & air conditioning. Please enjoy your stay!

11–18 Sep

$135 SGD per night

Guest favourite

Cottage in Upland

4.84 out of 5 average rating, 570 reviews

Cottage on 2nd NO Cleaning Fee Close to Taylor U.

No cleaning fees with your help! This is a quiet cottage getaway. Nestled in Upland, close to Taylor University, Indiana Wesleyan, and Ball State, this is a convenient location to have a relaxing stay. The cottage has two bedrooms, one bath, a fully stocked kitchen, and indoor/outdoor space to gather. You are welcome to enjoy a campfire in the yard or sit on the porch and enjoy the sunset. Come stay with us and enjoy all that Upland has to offer!

1–8 Dec

$161 SGD per night

Guest favourite

Home in Marion

4.99 out of 5 average rating, 164 reviews

Lindsay's Landing: 3-Bedroom, 2-Bathroom Home

This home is comfortable and stylish home with many amenities and is in an ultra-convenient location - a stone's throw from Indiana Wesleyan University, dining and shopping. Guests will love the open floor layout, full kitchen, high-speed internet, smart TV, and large beds with premium mattresses, pillows, and linens. You will feel right at home at Lindsay’s Landing. (Note: upon request, pets are welcome for a fee of $12/pet/night.)

2–9 Apr

$192 SGD per night

Guest favourite

Guest house in Ossian

4.96 out of 5 average rating, 247 reviews

Quiet Country Corner

Come enjoy the wide open country space in our quiet and peaceful guesthouse. Although you will be surrounded by solitude you will be just minutes from several towns. Enjoy the quiet of the surrounding fields and woods along with the beauty of the pond year round. The guesthouse is attached to our home but the garage is in between the two so it is very quiet for everyone. You will have your own private entrance.

8–15 Oct

$105 SGD per night