Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

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

4.77 out of 5 average rating, 44 reviews

Relaxi CABin

JacquelineRating, 5 stars3 weeks 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 stars4 weeks 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

An outdoor space features a wooden deck with a charcoal grill and a fire pit surrounded by built-in benches. Soft lighting from string lights above creates a cozy atmosphere. The deck is complemented by a patterned outdoor rug and a fenced backyard providing privacy.

Home in Champaign

5 out of 5 average rating, 7 reviews

Parkside home close to campus - 3 BD 2 BA

BlakeRating, 5 stars1 month ago

Sara was an amazing host! Her place was perfect for my last-minute stay. I am very picky so, I was happy to find that the house was spotlessly clean, with super comfy beds that made us feel right at home. On top of that, I asked for a restaurant recommendation, and she suggested Seven Saints - it was so good! Her hospitality and local tips made my stay even better. I couldn’t have asked for a more welcoming experience. Highly recommend staying here. Thank you, Sara!

Guest favorite

Home in Champaign

4.88 out of 5 average rating, 33 reviews

Extra Large Home w/ Chefs Kitchen Near UofI

JamiRating, 5 stars3 weeks ago

We were in the area for our daughter's basketball tournament and this house was perfect for our stay! Everything is exactly as described and very comfortable! Our dog loved the yard and was equally as content and loved our morning walks around the charming neighborhood. We stay in a lot of rentals and this was one of the best in terms of supplies and items to meet all needs. We will be back!

Guest favorite

A spacious wooden deck is surrounded by lush greenery, featuring a propane grill and a dining set with several chairs. String lights are hung above, creating a welcoming ambiance in the natural setting. The cabin's large windows offer views of the wooded surroundings.

Cabin in Bloomingdale

4.96 out of 5 average rating, 74 reviews

Treetops Cabin in the Woods!

NickRating, 5 stars4 days ago

This cabin and the area surrounding was even more beautiful than the photos. It overlooks a huge canyon that was fun to explore. The cabin itself was great and had all the amenities we needed to cook great meals. Was very impressed by the cooking utensils in the cabin, the view, Anna’s responsiveness, and the overall “bang for your buck” when it came to this property. Our group had a fantastic time. Lots of spaces in and on the property to relax and enjoy nature. Would highly recommend if looking to stay in this area.

Guest favorite

A wooden deck features two chairs positioned to offer views of Lake Vermilion. The surrounding trees create a natural frame, while the calm water reflects the greenery. The deck extends toward the lake, providing an inviting space for relaxation.

Home in Danville

4.95 out of 5 average rating, 20 reviews

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

DwayneRating, 5 stars2 weeks 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

An outdoor patio area features a square fire table surrounded by four wooden chairs. Lush green grass stretches out beyond the patio, with trees and open fields visible in the background, creating a serene setting for relaxation.

Cottage in Sullivan

5 out of 5 average rating, 211 reviews

Lakewood Cottage #1 @ Lake Shelbyville

RachelRating, 5 stars1 week ago

Loved our stay! We’ve stayed at lots of AirBnBs and this was hands-down the cleanest. The large yard was great for my boys. The amenities- from towels to bedding to games - were all clean and well-thought-out. This is a cozy little space for some time to get away. Convenient location for reaching Aikman Wildlife Adventure and Yoder’s restaurant.

Guest favorite

The exterior of the cabin features an A-frame design with large glass doors leading to the deck. Two comfortable chairs surround a round stone table, creating a space for relaxation. Lush trees provide shade, enhancing the tranquil outdoor setting.

Cabin in Ashmore

4.89 out of 5 average rating, 213 reviews

Sweet Dreams Cabin. Peaceful & Relaxing

MaureenRating, 5 stars1 week ago

Wonderful property, as advertised. I really enjoyed the cozy, cabin vibes. The cabin was small but bad everything we needed. I really appreciated the plentiful amount of towels in the bathroom and pillows and blankets for the couches. The bed in master bedroom was extremely comfortable. Also, the sheets smelled really good :) I would recommend this cabin to anyone who wants a cozy getaway.

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What guests are saying

Historic Home | Central Location & Pet-Friendly

4.86 out of 5 average rating, 22 reviews3 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.

Home in Terre Haute

What guests are saying

Lake Shelbyville Home with a View

4.9 out of 5 average rating, 49 reviews8 months ago

This is our second time staying here as a family. There are several reasons we came back: check in and out is very easy; the space accommodates our extended family very well; there is direct lake access though you have to be aware the path is “natural“ and as Doug has said in other reviews, they do not have control over improving the path; the space was very clean and all the essentials are provided; Doug is very responsive and got back to us very quickly when we had minor questions! We would highly recommend staying here, as long as it doesn’t interfere with the time we want to come back😁

Guest suite in Shelbyville

What guests are saying

Hidden Gem in the Woods: Lost Creek Lodge

5 out of 5 average rating, 10 reviews2 weeks ago

This house was absolutely perfect! Large, clean, quiet, and private. We rented it for a place to gather after our sister’s funeral. Twenty people fit comfortably for a meal and visiting. My wife, daughter, and I spent two nights, and the beds were comfortable. Megan was an amazing host! We had a little trouble with a bathroom lock, and she sent maintenance over right away. We will definitely stay here again.

Home in Terre Haute

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Popular amenities for Oakwood vacation rentals

Kitchen

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Oakwood

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, 32 reviews

Country home

LisaRating, 5 stars3 weeks ago

We visited from family for a birthday party. We are from Tennessee and thoroughly enjoyed this cozy country home. The open floor plan was nice and spacious and allowed our family to enjoy each other. We will definitely be back !!

Guest favorite

A wooden staircase leads down towards a serene, greenish-blue lake, framed by trees on either side. Sunlight casts gentle shadows on the steps, creating a natural pathway to the water's edge. The surrounding vegetation adds to the tranquil ambiance.

Home in Rockville

4.92 out of 5 average rating, 36 reviews

Peaceful Wooded Lake Cottage Retreat

BrittanyRating, 5 stars5 months ago

This home was beautiful and clean! Everything we were expecting and the host was very friendly and communicated great!!!

Guest favorite

Home in Terre Haute

4.77 out of 5 average rating, 22 reviews

Family Getaway: Indoor Pool, Sauna & Arcade

RobRating, 5 stars3 weeks ago

Was a cool place to ger away with the kids for thw weekend!

Guest favorite

Wooden stairs lead up through a rustic space, adorned with various vintage signs on the walls. A prominent yellow 'No Passing Zone' sign is attached to the railing, contributing to the quirky decor of the stairway.

Tower in Clinton

4.9 out of 5 average rating, 103 reviews

Griff’s Knob

BrandonRating, 5 stars4 days ago

Once again, a great stay in a very special place! thanks guys

Top guest favorite

A rustic cabin stands among lush greenery, featuring a wooden exterior and a covered porch. The surrounding landscape includes a stone path and a variety of plants, with a gravel driveway leading to the structure. The cabin is partially shaded by tall trees.

Cabin in Veedersburg

4.98 out of 5 average rating, 250 reviews

Rustic Cabin Getaway

PeterRating, 5 stars2 weeks ago

The cabin was perfectly secluded enough for the marriage vision retreat my wife and I planned. The place has beautiful surroundings and isn’t far from basic needs such as convenience or grocery stores. The cabin was clean and looked just like it did in the pictures. Thank you for a great stay, Megan!

Guest favorite

A modern kitchen features dark blue cabinetry contrasted by light wood accents. A central island with a granite countertop is accompanied by two black bar stools. Natural light filters in through a large window, illuminating the stylish pendant lighting above.

Home in Terre Haute

4.95 out of 5 average rating, 40 reviews

Charlotte’s

TraciRating, 5 stars3 months ago

The place was very spacious and comfortable. Just the right mix of modern and traditional, with a lot of room to spread out. The beds were extremely comfortable and there was plenty of TV areas, including a neat little room my husband named “man-cave” to watch TV. Overall, neat house that I would stay in again. I would vote it the best I have stayed in Terre Haute. Of note, four beds are upstairs in a spacious attic nook with a TV area and bathroom. The other two bedrooms are on the lower floor. Kelly and her husband were very responsive to any needs that we had, and when we ran into an issue they responded quickly. The house was great!

Top guest favorite

A circular fire pit area features smooth stones surrounded by several adirondack chairs in various colors. Lush trees provide shade, with a serene view of the lake visible through the foliage, offering a peaceful outdoor space for gathering.

Cabin in Rockville

5 out of 5 average rating, 62 reviews

Classic Lakefront Retreat on Raccoon Lake, USA

MichaelRating, 5 stars2 weeks ago

We highly recommend this house as a place to stay. It was extremely clean, everything about it was top notch! It was above and beyond our expectations. Jarad was just outstanding and if we ever come back to this area we will definitely be staying here again! Jared was so thoughtful he even reached out to us when a storm was headed our way to let us know that they have a generator. The storm did knock out the power, but the generator automatically kicked on within a couple of seconds and we were able to enjoy the entire evening with full electricity. We can't say enough wonderful things about this house!

Top guest favorite

A charming gray house with a black metal roof is situated on a gravel driveway. An American flag is displayed on the front porch, which features black railings. Lush trees provide greenery in the surrounding area, enhancing the serene ambiance.

Home in Urbana

5 out of 5 average rating, 8 reviews

2 Bed Home Near U of I

BarbRating, 5 stars1 week ago

Stayed at Justin’s place while visiting my son for mom’s weekend. Everything was perfect! One of the nicest homes I’ve stayed at. Justin was flexible with check in and very responsive to messages. The home was super clean and comfortable in a quiet area. The couches and throws in the living room were soft and so cozy for watching tv and reading. Every amenity you could possibly need was thoughtfully available. Really nice selection of snacks too. Highly recommend Justin’s place to anyone visiting the area. I hope to have a chance to stay here again!

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Vacation rentals in Oakwood

Top-rated vacation rentals in Oakwood

Raccoon Lake Retreat

Historic Home | Central Location & Pet-Friendly

Beach Vibes

Green House

Lake Shelbyville Home with a View

Raccoon Lake – Huge Vacation Home – Lakefront

Hot Tub,pets allowed,on creek,3 mi from Badlands

Hidden Gem in the Woods: Lost Creek Lodge

Critter Cove

Cozy and beautifully renovated!

Fort Harrison River Front

Van Allen - newly renovated single family home

Vacation rentals for every style

Popular amenities for Oakwood vacation rentals

Other great vacation rentals in Oakwood

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