Pioneer Holiday Rentals

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Holiday Rentals in Pioneer

Rest, Relax and Reboot...pet friendly

9.6 out of 10, Exceptional, (118)
"Very nice clean cottage with beautiful views. It was chilly and windy so we didn't take out the boats or kayaks so I guess we will have to come back. Rhonda stopped by to make we got checked in okay and didn't need anything. We thought that was above and beyond and it was appreciated. "
Rest, Relax and Reboot...pet friendly

Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything

8.6 out of 10, Excellent, (30)
"This place is a convenient location to the college. It’s an older home and is clean. It works just fine for my needs- a place to sleep and easy to get in and out."
The price is AU$199
includes taxes & fees
3 Dec - 4 Dec
Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything

Cozy home in historic Hillsdale

10.0 out of 10, Exceptional, (11)
"This is a lovely home for visiting our college students. It is very clean. We were able to cook a meal for our kids and a few friends of their friends. Heather was very responsive when I messaged her. I would stay here again. "
The price is AU$514
includes taxes & fees
27 Nov - 28 Nov
Cozy home in historic Hillsdale

Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed

9.4 out of 10, Exceptional, (42)
"X"
The price is AU$194
includes taxes & fees
5 Dec - 6 Dec
Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed

Modern Condo in Archbold - Near I-80

10.0 out of 10, Exceptional, (20)
"Overall great"
The price is AU$304
includes taxes & fees
25 Nov - 26 Nov
Modern Condo in Archbold - Near I-80

LAKE FRONT COTTAGE ON IYOPAWA ISLAND GOLF COURSE

9.6 out of 10, Exceptional, (39)
"What a great week away from the business of life. Great location: golf course across the street, on the lake for boating, sand bar, fishing, walking around the island, golf carting if you bring one, and great community of friendly people. We had 8 people stay comfortably, 1 restroom is a bit challenging but do able. Parking is a little struggle for day guests. Only 3 parking spots including 1 in the garage. But again all minor details that are over come by the location. Refrigerator/freezer in...
LAKE FRONT COTTAGE ON IYOPAWA ISLAND GOLF COURSE

Stunning lake front home & everything is new! Direct access to Nettle Lake!

10.0 out of 10, Exceptional, (101)
"I use to come here when I was a little girl. We stayed directly across the lake from my grandpas place.. Mike and Sue were extremely pleasant. Made us feel very comfortable. I would very much recommend this place! We are looking forward to our next vacation here"
Stunning lake front home & everything is new! Direct access to Nettle Lake!

Sleeps 11 - Bar Room - Game Room - Handicap Accessible

9.8 out of 10, Exceptional, (10)
"We booked this for a long weekend with the family to watch the eclipse and celebrate my nephew's birthday. The property was just as described; secluded, spacious, and quite charming. We had 6 adults, a 7 year old, and an 80 lb Rottweiler, and there was plenty of room for everyone. Lots of space for outdoor activities and even though you're literally 10 mins from civilization and a store, you feel like you're out in the middle of nowhere. The whole group said they'd definitely come back so if...
Sleeps 11 - Bar Room - Game Room - Handicap Accessible

4 bedroom Lake James Cottage with sandy beach and fishing pier

9.8 out of 10, Exceptional, (25)
"The property and the owner/hosts were fantastic. We had a wonderful week and had everything we needed. It was very comfortable for 3 couples and a guest or 2 that stopped by for a night. "
4 bedroom Lake James Cottage with sandy beach and fishing pier

Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed

8.2 out of 10, Very good, (24)
"Short drive to Hillsdale college. Bathroom layout was tight."
The price is AU$194
includes taxes & fees
1 Dec - 2 Dec
Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed

Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College

8.6 out of 10, Excellent, (24)
"Property has tons of character and was clean and well furnished! We were pleased with our stay and the communication with owner/manager! Thank you for the hospitality!"
The price is AU$194
includes taxes & fees
1 Dec - 2 Dec
Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College

Hillsdale County, Michigan: weddings, groups, Hillsdale College, Trine Univ.

10.0 out of 10, Exceptional, (62)
"Nick and Marisa provided a beautiful home for us. The accommodations and their graciousness exceeded our expectations. Thank you!"
Hillsdale County, Michigan: weddings, groups, Hillsdale College, Trine Univ.

Home away from home

9.8 out of 10, Exceptional, (20)
"Have stayed a few times. Good location and clean"
The price is AU$259
includes taxes & fees
24 Nov - 25 Nov
Home away from home

Experience lakefront luxury with spectacular views on Lake James, Indiana!

10.0 out of 10, Exceptional, (4)
"We had a great time. Property was as listed. Would go back again."
Experience lakefront luxury with spectacular views on Lake James, Indiana!

Breathtaking Lakefront View - Pontoon Available! Coldwater Chain of Lakes

9.8 out of 10, Exceptional, (36)
"Property was very clean, good communication with Josh. Nice centralized location to restaraunts. Lake has options, whether wanting the peacefullness of the sunset, or chances to go tubing. It was a great place to stay. Quiet neighbors."
Breathtaking Lakefront View - Pontoon Available! Coldwater Chain of Lakes

Berry Lake House

7.8 out of 10, Good, (9)
"It’s pretty much as advertised."
Berry Lake House

Cheerful lakefront cottage with kayaks and fire pit

10.0 out of 10, Exceptional, (44)
"Superbly clean, quaint, very well appointed and decorated, cozy lake home. A group of 5 friends and I met here for the weekend and had a marvelous stay. We enjoyed taking the kayaks out for a spin on beautiful Lake George, taking a long walk around the lake, and spending lots of time catching up and visiting in the cozy home. Beds were very comfortable too! Everything was perfect about this stay. Thank you very much for your amazing hospitality and sharing your home RJ and Stacey!!"
Cheerful lakefront cottage with kayaks and fire pit

Sunsets, Sunsets, Sunsets

9.4 out of 10, Exceptional, (6)
"We had a fantastic week at this cottage. The cottage was perfect for our family vacation. Jeff was very responsive to questions and replied quickly. Plenty of supplies were available. We were very comfortable. We would highly recommend this rental!"
Sunsets, Sunsets, Sunsets

Beautiful Lakefront Home with Tiki Bar overlooking Nettle Lake!! 3,200 Sqft.

9.4 out of 10, Exceptional, (38)
"We stayed here for a couple nights during the week in August. Everything was great. We had a fun time using the Kayaks and sitting down by the dock. It’s a small lake but was perfect for the kids to Kayak. The he house was clean and the neighbor we met was very nice. Perfect for a mid week getaway for my wife and kids and another couple and their daughter. "
Beautiful Lakefront Home with Tiki Bar overlooking Nettle Lake!! 3,200 Sqft.

Private Apartment in Historical Downtown Hillsdale

10.0 out of 10, Exceptional, (99)
"Perfect location! We were in town to check out Hillsdale College. Heather was very responsive and the whole experience could not have been easier. Very cool reno of the 2nd/3rd floors of an historic building in "downtown" Hillsdale. "
Private Apartment in Historical Downtown Hillsdale
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Pioneer you may be interested in

Days Inn by Wyndham Hillsdale

2.0 star property
7.2 out of 10, Good, (651)
"Hotel was nice and clean, hotel room was clean a spacious...not bad for the price"
The price is AU$131
includes taxes & fees
24 Nov - 25 Nov
Days Inn by Wyndham Hillsdale

Ramada by Wyndham Angola/Fremont Area

2.5 star property
6.2 out of 10, (1029)
"Nice area off the highway with outdoor adventures. There is a pool and breakfast. We have stayed here before this trip and will stay here again in the future."
The price is AU$118
includes taxes & fees
3 Dec - 4 Dec
Ramada by Wyndham Angola/Fremont Area

Holiday Inn Express & Suites Montpelier, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (637)
"C"
The price is AU$172
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Montpelier, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Pioneer?

Yes, there are holiday rentals close to the most popular sights in Pioneer, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pioneer has to offer?

Rest, Relax and Reboot...pet friendly: This holiday home rental outside of Pioneer is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Pioneer?

Explore the area and family-friendly sights such as Christmas Manor, or get out into nature at a spot like Harrison Lake State Park. In the wider area, you’ll find Williams County Fairgrounds and Stoney Ridge Winery.

What’s a holiday rental in Pioneer like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pioneer. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for small groups.