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Pioneer Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Pioneer vacation rentals

A spacious living room with a wooden floor, a ceiling fan, a green bookshelf, a floral sofa, a white armchair, and a dining table.

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, (24 reviews)
"Super cute & very clean! It was conveniently located next to the state park for walking and recreation."
United States
Kevin
$183 nightly
The price is $188
Oct 19 - Oct 20
Total with taxes and fees
Lake View Cottage for Two with Views of Harrison Lake
A rustic wooden building with a red door and a window labeled "Baths".

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
$85 nightly
The price is $85
Oct 18 - Oct 19
Total with taxes and fees
Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town
A bedroom with a wooden bed, a nightstand, a lamp, a chair, and a decorative wall piece.

3. 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, (49 reviews)
"I have stayed here before and had great experience. There were a couple of snafoos when I arrived but everything worked out in the end. The stairs going up to my place were not ideal but I survived. I want to thank Rebecca for all her help and kindness. I want to thank the wonderful Kenton for coming down the next morning to do a great job getting my room in tip top shape. And last but not least, Scott. He came down from the Pub to reset my lock to make sure I would be completely safe. I...
United States
Michelle
$105 nightly
The price is $108
Oct 26 - Oct 27
Total with taxes and fees
Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed
An aerial view of a parking lot with several cars, a large building with a dome, and surrounding buildings.

4. 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
$100 nightly
The price is $104
Oct 28 - Oct 29
Total with taxes and fees
Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything
A building with a gabled roof, a central window, and decorative elements including stars and a sun-like shape.

5. 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)
"Quaint homey feel."
United States
Kelleigh R.
$96 nightly
The price is $99
Oct 25 - Oct 26
Total with taxes and fees
Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed
A modern kitchen with white cabinets, stainless steel appliances, a central island with bar stools, and pendant lighting.

6. 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, (19 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
$303 nightly
The price is $319
Oct 27 - Oct 28
Total with taxes and fees
New Waterfront Guest House – Less than 10 Min to Hillsdale College
A compact kitchen with a washing machine, microwave, and sink.

7. 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
$191 nightly
The price is $191
Oct 26 - Oct 27
Total with taxes and fees
Tiny House near Hillsdale College
A bedroom with a four-poster bed, a small bedside table, and a window with a view of a parking lot.

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

Brand-New Lakefront Retreat on Nettle Lake Swim, Fish & Relax
Montpelier
10.0 out of 10, Exceptional, (1 review)
"Such a beautiful stay and the host was amazing!"
United States
Madisen Y.
$615 nightly
The price is $644
Oct 18 - Oct 19
Total with taxes and fees
Brand-New Lakefront Retreat on Nettle Lake Swim, Fish & Relax
A modern living room with a sectional sofa, a glass coffee table, and a painting on the wall.

9. Charming 3-bedroom house in Hillsdale near the College

Charming 3-bedroom house in Hillsdale near the College
Hillsdale
9.8 out of 10, Exceptional, (8 reviews)
"Spacious well equipped home!"
United States
Emily
$235 nightly
The price is $248
Oct 18 - Oct 19
Total with taxes and fees
Charming 3-bedroom house in Hillsdale near the College
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a wooden entertainment unit.

10. The Howder House / Refined 1BR / Sleeps 4

The Howder House / Refined 1BR / Sleeps 4
Hillsdale
10.0 out of 10, Exceptional, (2 reviews)
"Stay was perfect"
United States
Courtney H.
$160 nightly
The price is $168
Oct 25 - Oct 26
Total with taxes and fees
The Howder House / Refined 1BR / Sleeps 4
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

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.
$186 nightly
The price is $209
Oct 19 - Oct 20
Total with taxes and fees
Fox Lake Road Bungalow (Near Trine University)
A modern kitchen with white cabinetry, a stainless steel range hood, a built-in oven, a dishwasher, and a window providing natural light.

12. Cozy home in historic Hillsdale

Cozy home in historic Hillsdale
Hillsdale
9.8 out of 10, Exceptional, (40 reviews)
"Great home close to downtown and the college. Very convenient."
United States
Laura B.
$412 nightly
The price is $427
Oct 18 - Oct 19
Total with taxes and fees
Cozy home in historic Hillsdale
A modern living room with a grey sectional sofa, a wooden coffee table, and a TV on a wooden cabinet.

13. Trine University Gateway Villa

Trine University Gateway Villa
Angola
10.0 out of 10, Exceptional, (34 reviews)
"Great property, very clean and plenty of space for a family of 4."
United States
Cory W.
$171 nightly
The price is $192
Oct 19 - Oct 20
Total with taxes and fees
Trine University Gateway Villa
A covered porch with two chairs and a table, a lattice screen, and a potted plant.

14. Private home near Hillsdale Hospital

Private home near Hillsdale Hospital
Hillsdale
$309 nightly
The price is $309
Oct 18 - Oct 19
Total with taxes and fees
Private home near Hillsdale Hospital
A dock with two wicker lounge chairs facing a calm lake, surrounded by trees and houses.

15. LAKE JAMES Beautiful 4-bedroom cottage with Swimming, AC

LAKE JAMES Beautiful 4-bedroom cottage with Swimming, AC
Angola
10.0 out of 10, Exceptional, (1 review)
"Great lake house in an excellent location! It’s situated on the main lake while tucked back in a quiet, calm cove, making it the perfect spot for swimming. There are multiple outdoor spaces to relax and enjoy the beautiful views. The host was friendly, easy to communicate with, and responded to questions promptly. We had a wonderful stay and would definitely recommend this property!"
United States
Stephanie W.
$391 nightly
The price is $438
Oct 18 - Oct 19
Total with taxes and fees
LAKE JAMES Beautiful 4-bedroom cottage with Swimming, AC
A living room with a grey sectional sofa, a small wooden side table with a lamp, and a world map on the wall.

16. 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.
$264 nightly
The price is $295
Oct 18 - Oct 19
Total with taxes and fees
4-bedroom house in brilliant Angola with AC, WiFi. Enjoy your stay
A compact kitchen with a washing machine, dishwasher, and a window with blinds.

17. Modern home in Hillsdale walking distance to Hillsdale College

Modern home in Hillsdale walking distance to Hillsdale College
Hillsdale
$394 nightly
The price is $409
Oct 18 - Oct 19
Total with taxes and fees
Modern home in Hillsdale walking distance to Hillsdale College
A bedroom with a bed, dresser, ceiling fan, and a window with blinds.

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

The Fox Den • 2BR/2BA • Mins to Trine & Fox Lake
Angola
$147 nightly
The price is $165
Nov 17 - Nov 18
Total with taxes and fees
The Fox Den • 2BR/2BA • Mins to Trine & Fox Lake
A room with a wooden table, a vase with flowers, a window, and an American flag on the wall.

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

The Independence Inn near Hillsdale College: The Premiere Themed Stay
Hillsdale
$369 nightly
The price is $389
Oct 27 - Oct 28
Total with taxes and fees
The Independence Inn near Hillsdale College: The Premiere Themed Stay
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in dishwasher, and a coffee maker on the countertop.

20. 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, (4 reviews)
"Wonderful property! Clean, immaculate,…well stocked kitchen with dishes, utensils, etc. Comfortable beds, great towels!Everything felt newly updated. So close to the college, we could really almost walk to the Searle Center, but it was raining this weekend. Highly recommend this property!"
United States
Traci S.
$423 nightly
The price is $440
Oct 18 - Oct 19
Total with taxes and fees
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

Comfort Inn Fremont

Comfort Inn Fremont

10/10 Excellent
"Staff was great, room was clean and well kept plently of lighted parking and breakfast was from 6:30-9:30 giving plently of time to get it if wanted too"
Harold 1-night trip
Posted 3 days ago
Comfort Inn Fremont

Find out more about Pioneer

Everything you need to know about Pioneer vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pioneer vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pioneer vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pioneer vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pioneer. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pioneer in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $295 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pioneer rentals

At Expedia, we put the best Pioneer vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pioneer rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pioneer vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pioneer. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Pioneer?

Yes, there are vacation rentals close to the most popular local attractions in Pioneer, or you can go with a secluded option if you'd like a relaxing place to stay.

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

LUXURY COUNTRY RETREAT ~ PICKLEBALL COURT, FIRE PIT & COUNTRY VIEWS: This vacation home rental outside of Pioneer offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a patio and a selection of games.

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 larger area, you’ll find Nettle Lake and Harrison Lake State Park.

What’s a vacation rental in Pioneer like?

A vacation rental is a private property you can book for a few weeks or just a few days in Pioneer. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.