Holiday rentals in Oswego

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Top-rated holiday rentals in Oswego

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

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Top guest favourite
A cabin with green metal siding is situated beside a calm body of water. A wooden deck is adorned with chairs, and an outdoor fire pit is visible on a pebble-strewn area, while the landscape is complemented by greenery and trees in the background.
Cabin in Cherokee
4.95 out of 5 average rating, 77 reviews

K7 Depot

The K7 Depot Cabin sits directly next to a large body of water. Conveniently located 10 miles from Pittsburg and 30 miles from Joplin. THREE GUESTS MAX NO OUTSIDE GUESTS The Cabin sits approximately 100 feet from a short line railroad track. A very small train comes through an average of 2 times a day, 1 being in the middle of the night. Usually no train on Saturdays or Sundays. If you stand on the porch you might be able to get the conductor to honk his horn at you! Bank fishing is allowed

Top guest favourite
A rustic cabin exterior is framed by lush green grass and trees. The wooden structure features a stone chimney and a distinctive blue door, with two large windows on the left. A simple stone path leads to the entrance, inviting relaxation in a natural setting.
Cabin in Chanute
4.98 out of 5 average rating, 606 reviews

The Blue Door Cabin

If you want a retreat where you can sleep in, slow down and savor nature's beauty, the Blue Door Cabin, tucked in surprisingly hilly oak and hickory woods, with a beautiful view of the pond, is your destination. Within two hours from Kansas City, Tulsa, Joplin or Wichita, and only 4 miles from Chanute Kansas, this preserved and revived cabin offers an easy getaway for city dwellers in need of a very affordable anniversary weekend, study or solitude retreat, or family hiking and fishing trip.

Top guest favourite
Home in Frontenac
5 out of 5 average rating, 33 reviews

Southeast Kansas paradise!

Welcome to your home away from home in beautiful Frontenac- minutes from PSU, downtown Pittsburg & Frontenac. Fully updated 3-bed, 2-bath home w/all you need & MORE! Each of the 3 bedrooms features plush queen-sized bed w/ premium linens & stylish touches. 2 gorgeous modern baths & full sized washer/dryer. Fully equipped kitchen & cozy living room & game area. Enjoy the stunning in-ground swimming pool, indoor sauna, hot tub & outdoor dining area! (Pool open 5/15-10/31 weather permitting)

Top guest favourite
The silo structure is showcased against a vibrant sunset, with clouds reflecting shades of orange and pink. The grassy area in the foreground leads to a gravel driveway, while the building features a covered porch, inviting views of the surrounding landscape.
Barn in Vinita
4.98 out of 5 average rating, 61 reviews

Harvest Hill Silo- Route 66 Home w/ Fishing Pond

Setting on Route 66, just 2 miles from I44 Vinita exit, the silo is situated on 20acres and includes a stocked 5 acre pond for fishing and exploring! The bin has a full kitchen and a custom tiled shower in the downstairs bathroom. Downstairs also has a bedroom with a queen bed as well as a full size pull out. Upstairs has 1 bedroom with a twin over full bunk bed, 1/2 bath and a second living room with a queen size pullout. Enjoy the sunset or sunrise over looking cattle and horse pastures.

Top guest favourite
Cabin in McCune
5 out of 5 average rating, 22 reviews

Brand New Cabin w/ Hot Tub, Private Deck & Firepit

Built on a 40 acre old farmstead for maximum seclusion. Inside, the cabin features an open and inviting layout with a full kitchen, comfortable living space, and a cozy one-bedroom, one-bath design ideal for couples, solo travelers, or a small weekend getaway. A spacious outdoor deck to unwind in the hot tub, gather around the firepit in the evening, or take a peaceful walk along the nature trail. This cabin offers an experience that feels personal, calming, and genuinely refreshing.

Guest favourite
A modern two-story home features a covered porch with two outdoor chairs and hanging planters. The exterior displays a combination of light and dark siding, framed by a neatly landscaped yard. A single car garage is visible beside the driveway.
Home in Columbus
4.93 out of 5 average rating, 70 reviews

*New Construction* in downtown Columbus, KS!

Come experience what a microMansion home has to offer. Our most popular floor plan, The Smittle, has 2 bedrooms and 1 full bath, sleeping a family of 4 comfortably! Park in the single car garage and enjoy the spacious fenced yard with your pets (pet fee applies). We’re stocked with everything you’ll need for your trip. We’re close to Big Brutus, the best fishing and hunting spots, and several local venues. Longer term rentals welcome (see guidelines). We look forward to hosting you!

Top guest favourite
An above ground pool is surrounded by a well-maintained deck. The pool features two sturdy steps leading into the vibrant blue water. Lush green grass and trees are visible in the background, creating a serene outdoor setting.
Cottage in Joplin
4.99 out of 5 average rating, 465 reviews

The Hideaway

Welcome to your private hot tub & (Seasonal) above ground swimming pool!! ENJOY!! 👙 🌞 NO PARTIES. Your family will be close to everything when you stay at this centrally-located cottage. Carthage, Webb City & Joplin. Enjoy our quiet, peaceful, cozy cottage, equipped with a queen size bed & full size Lazy Boy hideabed. Sit on the wrap around porch & watch the deer & turkey stroll thru. We are located about 1 mile off Route 66 and easy access to I-49 & I-44.

Top guest favourite
A covered porch extends from a metal structure, warmly lit in the evening. A fire pit made of stone is positioned in the foreground, surrounded by grassy areas. Additional seating, a grill, and a boat can be seen on the porch, enhancing the outdoor living space.
Guest house in Cherokee
5 out of 5 average rating, 151 reviews

Bunkhouse on the Water

The Bunkhouse sits adjacent to a large body of water. Just 10 miles to Pittsburg and 30 miles to Joplin, MO. Guests can enjoy time outside on the covered porch next to the water, sit around the fire pit on those cool evenings, go for a hike, play a game of pickleball, or enjoy some catch and release fishing from the bank. Experience country living and sights and sounds of nature. Free range chickens also roam the property. 3 GUESTS MAX NO OUTSIDE GUESTS

Top guest favourite
A charming seating area features a wooden bench adorned with colorful cushions in warm tones of orange and yellow. A plaid throw drapes over the side, and natural light filters through a woven shade on the window, complementing the vibrant textures in the space.
Cottage in Chanute
4.96 out of 5 average rating, 346 reviews

A Little bit of Paradise @ Summit Hill Gardens

Summit Hill Gardens Cottage, a little bit of paradise, is a place to enjoy solitude, peace and quiet. Located rurally (3 miles south of Chanute, Ks), we are listed as one of the top ten attractions with numerous flower beds, a historic 1874 stone schoolhouse, a Retail Soap Shop located in a restored barn (handcrafted soaps are made here on site), and the Summit Hill Gardens Event Center- for hosting celebrations of life.

Top guest favourite
Tiny home in Galena
5 out of 5 average rating, 43 reviews

Bear Drive Cottage

Escape from the hustle and bustle of life for a quiet getaway in the Kansas countryside. Bear Drive Cottage features an acre of land, a westward facing view for enjoying Sunsets and a cozy modern feel for your time away from home. Gather around the fire pit in the evening, or use the kitchenette to make something to eat. This little gem just off of Historic Route 66 is just the spot to relax.

Guest favourite
A covered deck offers a comfortable seating area with two cushions and a spacious couch. Scenic views of the Neosho River and surrounding greenery are visible through the railing. The structure features a ceiling fan, enhancing the outdoor experience.
Holiday home in Chetopa
5 out of 5 average rating, 52 reviews

Cozy riverside cabin on the Neosho river

Enjoy this cozy 1 bedroom, 1.5 bath home with accommodations to sleep 6 nestled in the quaint little town of Chetopa. Enjoy the beautiful view of the Neosho River from the large private deck. Easy river access from the house for those who enjoy fishing. Full size kitchen with a dishwasher available. Coffee and wine bar onsite. Families can enjoy the city park with pool next door.

Guest favourite
An expansive wooden deck overlooks a calm river, with seating options including chairs and a table. A fan hangs from the ceiling, and decorative string lights enhance the serene outdoor space. Surrounding trees create a natural and tranquil backdrop.
Treehouse in Galena
4.95 out of 5 average rating, 105 reviews

The Treehouse Galena Kansas

Stairs and dock are available for easy access to the river. Great fishing. Kayaks and canoe available also tubes for floating. Continental breakfast, lots of drinks and snacks. Sit on the spacious deck and watch the wildlife. Enjoy the quiet surroundings. You won’t find a little vacation getaway any better in our area. Come experience the quiet & the beautiful surroundings.

Popular amenities for Oswego holiday rentals

  1. Airbnb
  2. United States
  3. Kansas
  4. Labette County
  5. Oswego