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Pioneer Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (23 reviews)
"Great time, nice lake!"
United States
Athanasius G.
$174 nightly
The price is $179
Sep 28 - Sep 29
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
Sep 25 - Sep 26
Total with taxes and fees
Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town
A rustic wooden building with a red door and a window labeled "Baths".

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.
$92 nightly
The price is $96
Sep 27 - Sep 28
Total with taxes and fees
Lost Nations Cowboy Town Bear Cabin
A rustic wooden building with a red door and a window labeled "Baths".

4. 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
$108 nightly
The price is $113
Sep 27 - Sep 28
Total with taxes and fees
Lost Nations Cowboy Town Mining Company Cabin
A rustic cabin with a wooden porch, a bench, and a sign indicating a deer hunting area.

5. 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
$98 nightly
The price is $98
Oct 5 - Oct 6
Total with taxes and fees
Lost Nations Cowboy Town Riverside Cabin
An aerial view of a parking lot with several cars, a large building with a dome, and surrounding buildings.

6. 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
Sep 30 - Oct 1
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.

7. 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
$109 nightly
The price is $113
Oct 4 - Oct 5
Total with taxes and fees
Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed
A compact kitchen with a washing machine, microwave, and sink.

8. 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
$206 nightly
The price is $206
Sep 30 - Oct 1
Total with taxes and fees
Tiny House near Hillsdale College
A bedroom with a wooden bed, a nightstand, a lamp, a chair, and a decorative wall piece.

9. 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 traveler
$109 nightly
The price is $113
Oct 12 - Oct 13
Total with taxes and fees
Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed
A bedroom with a bed, a mirror, and various framed pictures on the wall.

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

Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College
Hillsdale
8.4 out of 10, Very good, (29 reviews)
"Our son is a baseball player and we stay here every time we go down. Great location and price"
United States
Sue L.
$130 nightly
The price is $135
Oct 8 - Oct 9
Total with taxes and fees
Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College
A modern kitchen with white cabinets, stainless steel appliances, a central island with bar stools, and pendant lighting.

11. 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, (17 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 2 - Oct 3
Total with taxes and fees
New Waterfront Guest House – Less than 10 Min to Hillsdale College
A modern living room with a grey sectional sofa, a wooden coffee table, and a TV on a wooden cabinet.

12. 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.
$171 nightly
The price is $192
Sep 24 - Sep 25
Total with taxes and fees
Trine University Gateway Villa
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

13. 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.
$185 nightly
The price is $208
Sep 24 - Sep 25
Total with taxes and fees
Fox Lake Road Bungalow (Near Trine University)
A room with a flat-screen TV mounted above a fireplace.

14. 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.
$463 nightly
The price is $483
Oct 1 - Oct 2
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.

15. 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
$245 nightly
The price is $258
Oct 3 - Oct 4
Total with taxes and fees
Charming 3-bedroom house in Hillsdale near the College
A modern kitchen with white cabinetry, a stainless steel range hood, a built-in oven, a dishwasher, and a window providing natural light.

16. 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.
$411 nightly
The price is $426
Sep 24 - Sep 25
Total with taxes and fees
Cozy home in historic Hillsdale
A dock with two wicker lounge chairs facing a calm lake, surrounded by trees and houses.

17. 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.
$389 nightly
The price is $436
Oct 1 - Oct 2
Total with taxes and fees
LAKE JAMES Beautiful 4-bedroom cottage with Swimming, AC
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
$156 nightly
The price is $175
Oct 14 - Oct 15
Total with taxes and fees
The Fox Den • 2BR/2BA • Mins to Trine & Fox Lake
A living room with a grey sectional sofa, a small wooden side table with a lamp, and a world map on the wall.

19. 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.
$263 nightly
The price is $294
Sep 27 - Sep 28
Total with taxes and fees
4-bedroom house in brilliant Angola with AC, WiFi. Enjoy your stay
A covered porch with two chairs and a table, a lattice screen, and a potted plant.

20. Private home near Hillsdale Hospital

Private home near Hillsdale Hospital
Hillsdale
$309 nightly
The price is $309
Oct 2 - Oct 3
Total with taxes and fees
Private home near Hillsdale Hospital
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

The Lake House Retreat

The Lake House Retreat

8/10 Good
"We've stayed at this particular location in the past, when it was part of other chains, most recently Ramada, I believe. The current owners are busy renovating the property and while it remains a work in progress, we were impressed with what's been done so far. Our room had been renovated and was very nice, an improvement on our most recent previous stay at the location. Staff was very friendly and accommodating. Continental breakfast was fine (I'd suggest adding bagels or wheat bread to the options for toast). The hotel has an indoor pool that is large enough to allow for real exercise. I hope the owners will continued their efforts to remodel and improve the property and that travelers will give them a chance. We travel to the area frequently to visit family and will plan on staying there again."
Patrick 2-night trip
Posted 1 day ago
The Lake House Retreat

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 $98 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.