Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

A spacious hot tub is positioned on a wooden deck, softly lit with blue illumination, surrounded by tall trees. Steam rises gently from the water, suggesting a warm and relaxing environment, ideal for unwinding after a day outdoors.

Cabin in Rockville

4.76 out of 5 average rating, 45 reviews

Relaxi CABin

JacquelineRating, 5 stars1 month ago

It was beautiful and cozy. Def recommend renting the golf cart things are walking distance but it was so helpful and quick to explore and see things around the cabin. Robert was so welcoming great with instructions and very responsive. Felt like family the moment you got there and the home reflected that. Great spot for relaxing peace and fun with the family. Absolutely beautiful and first vacation kids put down the electronics got along and played together. Great home and host, you will enjoy!

Guest favorite

An outdoor patio area is illuminated by string lights, creating a warm ambiance against the evening sky. A small table and chairs are positioned nearby, while cornfields are visible in the background, enhancing the rural setting.

Farm stay in Georgetown

4.9 out of 5 average rating, 126 reviews

Farm Escape w/Nature Views, Central Location

MaddieRating, 5 stars1 month ago

We loved our stay at Kaloni's place. Her barndominium is just close enough to Georgetown to feel connected, but just far away enough to feel private. Kaloni is a responsive and welcoming host and we felt well taken care of! We'll probably stay here again in the future!

Guest favorite

A welcoming living area features a comfortable sofa and armchair, paired with a decorative area rug. A flat-screen TV is mounted near a stone fireplace, surrounded by natural light from the windows. Indoor plants add a touch of greenery to the space.

Cottage in Effingham

4.94 out of 5 average rating, 518 reviews

Centrally located, Peaceful Cabin by the Beach

TomRating, 5 stars1 day ago

We have stayed at Kristen's place multiple times now with our pets and it is our go to in the area. Waterfront cottage with an up north feel, close to shopping, restaurants and easy access to the highway. We will definitely be back again and recommend it to anyone looking for a nice getaway or even a quick overnight stay when passing through the area.

Guest favorite

Cottage in Decatur

4.9 out of 5 average rating, 115 reviews

Private Dock, Kayaks, Paddleboard - Relax & Play!

Germaid S.Rating, 5 stars2 weeks ago

Lovely house on the lake. The house is on three levels, so lots of space to spread out. The host was very communicative, supplied us with lots of recommendations, and was responsive. Overall a 5-star experience. Loved the deck to hang out on.

Guest favorite

A wooden deck extends over a serene pond, framed by greenery. Two black Adirondack chairs are positioned for relaxation, overlooking the water. The surrounding area is graced with a mix of trees and open space, under a bright blue sky dotted with clouds.

Home in Sullivan

4.97 out of 5 average rating, 114 reviews

Lake Shelbyville-Lakeside Villas

MycaRating, 5 stars2 days ago

We had a relaxing time staying at this wonderful place for two nights. The house has plenty of space, was well-stocked and was quite peaceful. We particularly enjoyed having coffee and breakfast on the back deck, where it seems you’re the only people in the world. The basketball court, swings and lovely sitting area by the pond were also a huge bonus in this space. There were multiple MASSIVE catfish and cute little fishies to feed and watch, which made it that much more special. Thanks for a great wonderful getaway!

Guest favorite

A wooden dock leads to the calm waters, flanked by two kayaks resting on the side. A gradual staircase rises from the dock, surrounded by trees, leading to the house set up on the hill. Soft lighting enhances the serene evening ambiance.

Home in Danville

4.95 out of 5 average rating, 20 reviews

Gorgeous Lake House! Sleeps 12, 5 BRs, 4 BAs!

DwayneRating, 5 stars1 month ago

Extremely helpful due to the situation on why we needed such a big house. House was clean, kept all the guests comfortable and able to stay busy with darts, pool table, and hot tub. Host always responded in a reasonable time.

Top guest favorite

The cottage exterior is illuminated at night, featuring a welcoming porch with wooden columns. Two rocking chairs and a small table are positioned on the porch, surrounded by seasonal decorations. The pathway is lined with smooth stones, leading to the entrance.

Cottage in Sullivan

5 out of 5 average rating, 213 reviews

Lakewood Cottage #1 @ Lake Shelbyville

MeganRating, 5 stars3 days ago

My husband and I spent two nights in this cottage with two of our close friends. The location is fantastic, quiet, and very private … it is located only a couple minutes drive to the quaint town of Sullivan, but you would never know with how private as it feels ! Marissa was very helpful. Anytime I reached out, (which was several) her responses were quick and helpful every time. At one point we had a glitch with the dryer knob and she and her husband showed up promptly and took care of the problem. Everything went smoothly for the rest of the time we were there. The house is immaculate, and all of the thoughtful touches are spot on. We have stayed at several Airbnb‘s and I believe this is one of my favorites! The kitchen is very well stocked with high-quality items and we never needed anything that wasn’t available. We prepared three meals each day and had all th supplies we wouldhave used at home. It looks exactly like the pictures and everything was modern and in great condition.

Guest favorite

A small floating dock is visible on calm water, equipped with a simple chair and surrounded by lush greenery. The water reflects the surrounding trees, creating a serene setting ideal for relaxation and fishing.

Home in Brazil

4.92 out of 5 average rating, 311 reviews

Swans Nest

ChristinaRating, 5 stars2 weeks ago

I found out I was going to have a weekend off after 4 months. I decided I needed to get away to sometime more peaceful. We had been to the area in the past to visit the Inidana State Sanatorium and my son wanted to go for another visit. I stumbled upon Andrea's place, and it was pet friendly. My first time bringing my pooches. Her property is beautiful and everything I was looking for. The home is spacious and clean. I loved the outside sitting areas. Good place to listen to nature, the small river and have a cup of coffee in the morning, or have a relaxing drink in the evening. There are a few paddle boats on the property. So much fun! And a swimming hole on the other side. Andrea is a lovely host, so friendly and happy to know you're enjoying yourself and the space she provides. I would definitely recommend her property and would love to visit again when I need some time away

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Popular amenities for Oakland vacation rentals

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Other great vacation rentals in Oakland

Superhost

A compact kitchen design features a bar counter with two stools, providing a casual dining space. The sink is positioned under windows covered with dark blinds, while a black door leads to the pantry area. Modern appliances are stored in sleek cabinetry.

Home in Sullivan

4.91 out of 5 average rating, 11 reviews

Country rental

AshleyRating, 5 stars1 month ago

Was a very nice stay! Didn’t have any issues and was a well kept house

Guest favorite

A spacious kitchen and dining area features a round table set with a neutral tablecloth, surrounded by wooden chairs. The kitchen showcases wooden cabinetry and equipped countertops, while a large rug adds a touch of warmth to the space. Natural light filters through the windows.

Home in Clinton

4.88 out of 5 average rating, 33 reviews

Country home

ChelsieRating, 5 stars3 weeks ago

Penny had things ready for us when we got there. It was very clean and open and peaceful. Her clean up instructions were clear. Any communication she made was clear and concise.

Superhost

The exterior of a charming vintage home is depicted, featuring a yellow facade with white trim. A spacious covered porch is seen at the front, surrounded by trees showcasing autumn foliage. The gabled roof and brick chimney add to the home’s historical character.

Home in Terre Haute

4.86 out of 5 average rating, 22 reviews

Historic Home | Central Location & Pet-Friendly

CarlosRating, 5 stars4 months ago

My family and I had a great experience at Lauren’s house. The house was clean, well maintained, and very charming….exactly as described and as shown in the pictures. Lauren was very communicative and accommodating. The check-in/out process was a breeze. In short, we had a great time staying at Lauren’s place and would recommend her property to others without hesitation.

Guest favorite

A spacious two-story house is nestled beside a calm lake, with a large deck overlooking the water. A private dock with a red roof provides boat slips. Surrounding trees offer shade, enhancing the tranquil lakeside setting.

Home in Effingham

4.98 out of 5 average rating, 83 reviews

Haven on the Lake-Swim/Fishing Dock-8 Beds-2 Baths

LoriRating, 5 stars1 month ago

My family rented the house for a couple of days for a quick family reunion. The house was great, had plenty of space for all of us. It had everything you could need and was well equipped. We are hoping to make this an annual event and this is our house of choice.

Top guest favorite

A serene outdoor area features a fire pit surrounded by a circular stone border on grassy terrain. A hammock is hung between two trees nearby, with a picnic table offering a space for relaxation. Logs are neatly stacked against a tree, enhancing the natural setting.

Cabin in Linton

5 out of 5 average rating, 55 reviews

Little Red Cabin

RobertRating, 5 starstoday

My fishing buddy and I have been coming to the Greene-Sullivan State Forest for years, and Rich's place is definitely our favorite place we've ever stayed. Surrounded by the lake and tucked back in the woods, it is very peaceful and secluded. We enjoyed the outside patio and gas grill area. The home is well stocked with everything you need. We will be back!

Superhost

An outdoor space featuring a stone patio extends underneath a wooden deck, supported by sturdy columns. Chairs are arranged along the patio, offering views of the water. Trees line the edge of the property, providing a natural backdrop to the tranquil setting.

Cabin in Rockville

4.86 out of 5 average rating, 69 reviews

Raccoon Lake – Huge Vacation Home – Lakefront

DiegoRating, 5 stars3 months ago

Really nice housefor family and friends! Super cozy, with super comfy furniture. Everything you need and more! Big kitchen, lots of things to do, games, movies (dvds)… The owner responses were always fast and friendly. A place to revisit

Guest favorite

The exterior of a cozy apartment is visible, featuring a covered porch with a swing, bordered by well-maintained grass. Surrounding greenery adds a natural touch, while the driveway and nearby structures contribute to a peaceful outdoor atmosphere.

Apartment in Shelburn

4.92 out of 5 average rating, 39 reviews

Gorgeous Apartment-Quiet Street.

VincentRating, 5 stars3 months ago

Stayed here only one night for a quick stop but would love to come back to the area for the nature and a longer stay. House was very nice and clean and the bed was comfortable.

Superhost