Oakland Vacation Rentals

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Check prices for these dates

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Nov 22 - Nov 23
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Nov 23 - Nov 24
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Nov 28 - Nov 30
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Dec 5 - Dec 7

Vacation Rentals in Oakland

Terrace/patio
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Paris
9.4 out of 10, Exceptional, (8)
"Great escape to get away and relax. The bird sounds were amazing! Fantastic amenities as well."
United States
Hollie D.
The price is ￥42,090
￥73,616 total
includes taxes & fees
Nov 30 - Dec 1
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Fridge, microwave, oven, stovetop
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois

Arthur
10.0 out of 10, Exceptional, (56)
"Easy to get to, close to the cute Main Street and also to the Amish markets!"
United States
Devin
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
Interior
The Ca BIN

The Ca BIN

Charleston
10.0 out of 10, Exceptional, (7)
"The CaBIN is nothing short of amazing. Beautiful location not too far from local stores and restaurants. The inside is spacious and beautifully decorated. The owners made sure we had everything we needed for our stay. Hospitality at it's finest. 100% recommend!"
United States
Melody Y.
The Ca BIN
Property grounds
Charming A-frame cabin set in the woods overlooking deep wooded ravines.

Charming A-frame cabin set in the woods overlooking deep wooded ravines.

Charleston
10.0 out of 10, Exceptional, (1)
Charming A-frame cabin set in the woods overlooking deep wooded ravines.
Fridge, microwave, oven, stovetop
Brickway Retreat

Brickway Retreat

Mattoon
9.8 out of 10, Exceptional, (38)
"Nice and clean home. "
United States
Kelly J.
The price is ￥17,205
￥28,180 total
includes taxes & fees
Nov 25 - Nov 26
Brickway Retreat
Exterior
A frame getaway on the Embarrass River in Charleston, Illinois

A frame getaway on the Embarrass River in Charleston, Illinois

2.0 star property
Charleston
10.0 out of 10, Exceptional, (7)
"We had such a wonderful stay with Becca and Craig--they are excellent hosts and the experience of peace and solitude in their space is unmatched! We are looking forward to another stay here in the future "
United States
Remy B.
A frame getaway on the Embarrass River in Charleston, Illinois
Fridge, microwave, oven, stovetop
The little house

The little house

Charleston
8.0 out of 10, Very Good, (1)
"Property was nice and comfortable, tucked away on a quiet street. The host were super nice and were such a pleasure to work with. Great spot close to everything."
United States
Dominick R.
The little house
Smart TV, printers
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions

Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions

Charleston
8.0 out of 10, Very Good, (2)
"It worked perfectly for us."
United States
conrad w.
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions
Property grounds
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!

Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!

2.0 star property
Charleston
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!
House (2 Bedrooms) | Interior
Country Home Near EIU & Lake Charleston!

Country Home Near EIU & Lake Charleston!

3.0 star property
Charleston
Country Home Near EIU & Lake Charleston!
Outdoor pool
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

Great home to unwind 15 minutes from Champaign Urbana and University of Illinois

Sidney
10.0 out of 10, Exceptional, (20)
"We had a wonderful time."
United States
Jayne P.
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
Interior
Newly updated and cozy home! Located near downtown!

Newly updated and cozy home! Located near downtown!

Mattoon
9.2 out of 10, Wonderful, (15)
"I am never disappointed when I stay here. Thanks for another great place to stay. Always clean, always comfortable, always welcoming! "
United States
Matthew W.
Newly updated and cozy home! Located near downtown!
Outdoor dining
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

Marshall
9.8 out of 10, Exceptional, (23)
"Thanks Anna for all your help and hospitality!"
United States
Julie B.
The price is ￥32,690
￥66,471 total
includes taxes & fees
Dec 1 - Dec 2
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Smart TV
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

Mattoon
10.0 out of 10, Exceptional, (1)
"Had a great time with our family and it was close to arthur"
United States
Daniel S.
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
Smart TV, fireplace, books, offices
A Luxury Family Mill Creek Lake Retreat

A Luxury Family Mill Creek Lake Retreat

Marshall
10.0 out of 10, Exceptional, (69)
"Awesome family vacation "
United States
Dot T.
A Luxury Family Mill Creek Lake Retreat
Interior
Updated spacious 2 br Flat

Updated spacious 2 br Flat

Mattoon
9.0 out of 10, Wonderful, (2)
"I stayed here for a long term rental while I worked at the hospital and it was perfect. Great distance and great location in town. Definitely recommend."
United States
Emma H.
Updated spacious 2 br Flat
Property grounds
Bell Tent Under the Stars

Bell Tent Under the Stars

Charleston
The price is ￥7,038
￥10,775 total
includes taxes & fees
Nov 23 - Nov 24
Bell Tent Under the Stars
Microwave, oven, stovetop, dishwasher
Bring The Whole Crew, We've Got Room!

Bring The Whole Crew, We've Got Room!

Mattoon
Bring The Whole Crew, We've Got Room!
Fridge, microwave, oven, stovetop
Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL

Charleston
10.0 out of 10, Exceptional, (8)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is ￥23,462
￥30,834 total
includes taxes & fees
Nov 23 - Nov 24
Cozy 2BR Loft in Downtown Charleston, IL
House (5 Bedrooms) | Interior
Beautifully Restored Farmhouse in Marshall!

Beautifully Restored Farmhouse in Marshall!

3.0 star property
Martinsville
Beautifully Restored Farmhouse in Marshall!
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 Oakland Hotel Reviews

Baymont by Wyndham Tuscola

Baymont by Wyndham Tuscola

10/10 Excellent
"Nice touches made this affordable motel better than most. I can tell people care to make it pleasant. Breakfast was thoughtfully simple. Everything I need. "
Susan 1-night trip
Posted 5 days ago
Baymont by Wyndham Tuscola

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
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  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

Frequently asked questions

Are there vacation rentals in Oakland?

Yes, there are vacation rentals near popular sights in Oakland, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Oakland?

Brickway Retreat: This vacation home rental outside of Oakland is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Oakland?

While you're exploring the area, Rockome Gardens and Kelly Moore Memorial Park are a couple of picturesque spots to get outside and enjoy nature. Walnut Point State Park and Eastern Illinois University are a couple of places you'll find in the larger area.

What are vacation rentals like in Oakland?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Oakland. Vacation rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.