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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Oakland vacation rentals

A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

1. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (15 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is AED 551
AED 724 total
includes taxes & fees
26 Oct - 27 Oct
Cozy 2BR Loft in Downtown Charleston, IL
A camper parked in a grassy area with a picnic table, a red umbrella, and a fire pit.

2. 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!
Charleston
10.0 out of 10, Exceptional, (3 reviews)
"Becca met me upon my arrival and helped take my things to the camper. She made sure I had everything I needed and said if there was anything I forgot or needed, to just ask. I didn't get to enjoy the trails as much as I wanted, because this was a working retreat for me. I would remind guests to bring bug repellent in case you do walk the trails to keep mosquitoes at bay. There are many friendly chickens in the area and there were two deer outside the camper this morning. The kitchen had...
United States
Wendy D.
The price is AED 374
AED 513 total
includes taxes & fees
7 Oct - 8 Oct
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!
A cozy cabin interior with a wooden staircase, a fireplace, a Christmas tree, and a leather sofa.

3. Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.6 out of 10, Exceptional, (15 reviews)
"Knowing we were checking in to a log cabin, we were not expecting it to be so clean and nice! The cabin is spacious, with plenty of comfortable seating, as well as lots of work space and storage, especially in the kitchen. The place seems to be new and is well cared for. Loved the setting! It is a beautiful, wooded property with plenty of privacy, but yet only 15-20 minutes from town. We enjoyed our stay very much!"
United States
Barbara A.
The price is AED 992
AED 1,756 total
includes taxes & fees
2 Oct - 3 Oct
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
A covered outdoor seating area with a glass table, cushioned chairs, and a sofa.

4. FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (29 reviews)
"The house was clean and stocked with everything we needed for our 2 night stay. Beds were comfortable. Host was very quick to answer questions."
United States
Melani S.
The price is AED 915
AED 1,752 total
includes taxes & fees
2 Oct - 3 Oct
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
A tent set up on a wooden platform surrounded by trees.

5. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is AED 198
AED 288 total
includes taxes & fees
2 Oct - 3 Oct
Bell Tent Under the Stars
A kitchen with a white stove, wooden walls, and a wooden staircase.

6. The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood

The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
Arthur
The price is AED 380
AED 777 total
includes taxes & fees
6 Oct - 7 Oct
The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
A brick house with a white door, a mailbox, and a wooden porch.

7. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (53 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
The price is AED 404
AED 662 total
includes taxes & fees
6 Oct - 7 Oct
Brickway Retreat
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

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?

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois : This vacation home rental outside of Oakland is located in the city center and has a patio, a barbecue grill, and air-conditioning to put you at ease 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 and your friends and family can relax into your vacation with amenities like a selection of books.

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.