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Pioneer Holiday Rentals

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Our top choices for Pioneer holiday rentals

1. Lake View Cottage for Two with Views of Harrison Lake

Lake View Cottage for Two with Views of Harrison Lake
Fayette
10.0 out of 10, Exceptional, (22 reviews)
"Great time, nice lake!"
United States
Athanasius G.
The price is NZ$318
includes taxes & fees
14 Sept - 15 Sept
Lake View Cottage for Two with Views of Harrison Lake

2. Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town

Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town
Pittsford
10.0 out of 10, Exceptional, (2 reviews)
"The fishing is awesome!"
United States
Jesse
The price is NZ$135
includes taxes & fees
13 Sept - 14 Sept
Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town

3. Lost Nations Cowboy Town Bear Cabin

Lost Nations Cowboy Town Bear Cabin
Pittsford
10.0 out of 10, Exceptional, (4 reviews)
"Nice little place , full of beautiful art and scenery. Friendly host"
United States
zachary D.
The price is NZ$166
includes taxes & fees
21 Sept - 22 Sept
Lost Nations Cowboy Town Bear Cabin

4. Lost Nations Cowboy Town Riverside Cabin

Lost Nations Cowboy Town Riverside Cabin
Pittsford
9.0 out of 10, Wonderful, (11 reviews)
"A unique unforgettable stay. Friendly hosts, a sweet rescue horse, barn cats and kittens, a charming atmosphere. We had the river side cabin, which is just a short hike away. Cozy, far enough away to feel private, close enough to get visits from Midnight (a cat!)."
United States
Daphne
The price is NZ$189
includes taxes & fees
14 Sept - 15 Sept
Lost Nations Cowboy Town Riverside Cabin

5. Lost Nations Cowboy Town Mining Company Cabin

Lost Nations Cowboy Town Mining Company Cabin
Pittsford
9.2 out of 10, Wonderful, (10 reviews)
"Holly is amazing. Her husband is a great help as well. I have stayed there twice now. This time was even more fun with having a horse back riding experience! We stayed for a couples night out. There were no spider webs in our cabin and we didn’t have to worry about asking for batteries for our fan! The accommodations for being a Rustic style experience were wonderful and clean. We definitely be going back."
United States
Darci
The price is NZ$179
includes taxes & fees
23 Sept - 24 Sept
Lost Nations Cowboy Town Mining Company Cabin

6. Tiny House near Hillsdale College

Tiny House near Hillsdale College
Hillsdale
10.0 out of 10, Exceptional, (1 review)
"This tiny house was exactly what I was looking for. It was clean, comfortable, and had everything I needed without feeling cramped. The space was thoughtfully laid out, and I really appreciated how peaceful it was. It was also close to get to Hillsdale College, while still giving me the feeling of being away from everything. For a quick overnight stay, it was perfect. I would definitely recommend it to anyone visiting the area who wants something a little different from a traditional hotel....
United States
Cyndi
The price is NZ$351
includes taxes & fees
5 Oct - 6 Oct
Tiny House near Hillsdale College

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

Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed
Hillsdale
9.0 out of 10, Wonderful, (48 reviews)
"Enjoyed the stay."
United States
Anonymous traveller
The price is NZ$203
includes taxes & fees
20 Sept - 21 Sept
Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed

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

Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed
Hillsdale
8.4 out of 10, Very good, (29 reviews)
"On main drag so easy to fo d"
United States
debra
The price is NZ$195
includes taxes & fees
7 Oct - 8 Oct
Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed

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

Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything
Hillsdale
8.6 out of 10, Excellent, (35 reviews)
"Was a great stay at a place with a lot of history! Will look to stay here again if I’m in the area!"
United States
Carter
The price is NZ$195
includes taxes & fees
20 Sept - 21 Sept
Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything

10. New Waterfront Guest House – Less than 10 Min to Hillsdale College

New Waterfront Guest House – Less than 10 Min to Hillsdale College
Osseo
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful and peaceful place to stay. Others should know that water is not suitable for swimming, but very relaxing to enjoy with morning coffee or evening drinks. Thanks for sharing your lovely place Teresa and Glenn"
Canada
Teresa
The price is NZ$538
includes taxes & fees
20 Sept - 21 Sept
New Waterfront Guest House – Less than 10 Min to Hillsdale College

11. Fox Lake Road Bungalow (Near Trine University)

Fox Lake Road Bungalow (Near Trine University)
Angola
10.0 out of 10, Exceptional, (33 reviews)
"Very ideal for family stay"
United States
Katina T.
The price is NZ$357
includes taxes & fees
13 Sept - 14 Sept
Fox Lake Road Bungalow (Near Trine University)

12. Cozy home in historic Hillsdale

Cozy home in historic Hillsdale
Hillsdale
9.8 out of 10, Exceptional, (40 reviews)
"Great property in Hillsdale! Plenty of parking and room. Attentive and helpful host."
United States
Renata S.
The price is NZ$731
includes taxes & fees
13 Sept - 14 Sept
Cozy home in historic Hillsdale

13. Brand-New Lakefront Retreat on Nettle Lake Swim, Fish & Relax

Brand-New Lakefront Retreat on Nettle Lake Swim, Fish & Relax
Montpelier
The price is NZ$843
includes taxes & fees
1 Oct - 2 Oct
Brand-New Lakefront Retreat on Nettle Lake Swim, Fish & Relax

14. Trine University Gateway Villa

Trine University Gateway Villa
Angola
10.0 out of 10, Exceptional, (34 reviews)
"Loved the stay – beautiful home, very clean and accommodating!"
United States
Sean P.
The price is NZ$376
includes taxes & fees
6 Oct - 7 Oct
Trine University Gateway Villa

15. 4-bedroom house in brilliant Angola with AC, WiFi. Enjoy your stay

4-bedroom house in brilliant Angola with AC, WiFi. Enjoy your stay
Angola
9.4 out of 10, Exceptional, (6 reviews)
"The house was clean, warm, and welcoming. The large kitchen and dining area was great for family meals and games. Extra seating at the island allowed all of us to be together in the same space. The neighborhood was quiet and traffic noise was minimal. The large fenced in yard was a bonus too! We thoroughly enjoyed our stay and highly recommend this property to others."
United States
Karen M.
The price is NZ$508
includes taxes & fees
13 Sept - 14 Sept
4-bedroom house in brilliant Angola with AC, WiFi. Enjoy your stay

16. Modern home in Hillsdale walking distance to Hillsdale College

Modern home in Hillsdale walking distance to Hillsdale College
Hillsdale
The price is NZ$702
includes taxes & fees
14 Sept - 15 Sept
Modern home in Hillsdale walking distance to Hillsdale College

17. The Fox Den • 2BR/2BA • Mins to Trine & Fox Lake

The Fox Den • 2BR/2BA • Mins to Trine & Fox Lake
Angola
The price is NZ$298
includes taxes & fees
6 Oct - 7 Oct
The Fox Den • 2BR/2BA • Mins to Trine & Fox Lake

18. The Independence Inn near Hillsdale College: The Premiere Themed Stay

The Independence Inn near Hillsdale College: The Premiere Themed Stay
Hillsdale
The price is NZ$648
includes taxes & fees
12 Oct - 13 Oct
The Independence Inn near Hillsdale College: The Premiere Themed Stay

19. Close to Hillsdale College in a modern home with dedicated work space

Close to Hillsdale College in a modern home with dedicated work space
Hillsdale
10.0 out of 10, Exceptional, (2 reviews)
"Great home within very close walking distance to Hillsdale’s campus. Super comfortable beds. Heather was very easy to communicate with and responded to all questions!"
United States
Katrina T.
The price is NZ$751
includes taxes & fees
13 Oct - 14 Oct
Close to Hillsdale College in a modern home with dedicated work space
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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Top Pioneer Hotel Reviews

Find out more about Pioneer

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pioneer holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pioneer. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pioneer. Seeing all the best attractions is bound to make you fall in love with Pioneer. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pioneer short-term rentals, that won’t be hard to do.

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 Lake Diane. In the wider area, you’ll find Nettle Lake and Harrison Lake State Park.

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.