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Osgood Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Osgood vacation rentals

A living room with a coffee table, a brown leather sofa, a dining area with chairs, and a door with a stained glass window.

1. Charming 1-bedroom house in enjoyable Milan with AC

Charming 1-bedroom house in enjoyable Milan with AC
Milan
9.6 out of 10, Exceptional, (5 reviews)
"Exactly what we were looking for "
United States
Mark H.
$200 nightly
The price is $215
Sep 26 - Sep 27
Total with taxes and fees
Charming 1-bedroom house in enjoyable Milan with AC
A modern kitchen with a stainless steel refrigerator, white cabinets, and a large window.

2. The Beach House

The Beach House
Trenton
10.0 out of 10, Exceptional, (10 reviews)
"Everything was perfect .. will stay again! "
United States
Deborah
$158 nightly
The price is $177
Sep 29 - Sep 30
Total with taxes and fees
The Beach House
A modern kitchen with a built-in refrigerator and a window.

3. The Honeymoon Hideaway

The Honeymoon Hideaway
Trenton
10.0 out of 10, Exceptional, (6 reviews)
"Host was very welcoming and communicative! Great place!"
United States
Swank H.
$158 nightly
The price is $177
Sep 29 - Sep 30
Total with taxes and fees
The Honeymoon Hideaway
A compact kitchen with a built-in oven, a refrigerator, and a washing machine.

4. The City Loft

The City Loft
Trenton
10.0 out of 10, Exceptional, (6 reviews)
"We have stayed at the Loft several times and it is always clean, comfortable and inviting. "
United States
Craig A.
$179 nightly
The price is $200
Sep 27 - Sep 28
Total with taxes and fees
The City Loft
A living room with a brown leather sofa, a wooden coffee table, and a patterned rug.

5. Cheerful 2 Bedroom Home In Trenton City

Cheerful 2 Bedroom Home In Trenton City
Trenton
10.0 out of 10, Exceptional, (6 reviews)
"Nice, cozy home. Perfect for a couple or family with small children. "
United States
Melissa
$154 nightly
The price is $158
Sep 27 - Sep 28
Total with taxes and fees
Cheerful 2 Bedroom Home In Trenton City
A rustic kitchen with wooden walls, a stone countertop, and a stainless steel refrigerator.

6. The Lodge

The Lodge
Trenton
10.0 out of 10, Exceptional, (5 reviews)
"very quiet area, loved the decor."
United States
Angela
$190 nightly
The price is $213
Sep 27 - Sep 28
Total with taxes and fees
The Lodge
A living room with a sofa, armchairs, a coffee table, and a rug.

7. The Green House! Sleeps 12

The Green House! Sleeps 12
Trenton
10.0 out of 10, Exceptional, (10 reviews)
"Absolutely wonderful and will stay again "
United States
Steve K.
$239 nightly
The price is $245
Sep 27 - Sep 28
Total with taxes and fees
The Green House! Sleeps 12
A modern two-story house with a dark exterior, a covered porch, and a gravel driveway.

8. The Stables

The Stables
Trenton
9.8 out of 10, Exceptional, (18 reviews)
"Stayed at this property many times over the years and all the cabins are great. "
United States
Jennifer C.
$166 nightly
The price is $185
Sep 27 - Sep 28
Total with taxes and fees
The Stables
A bedroom with a wooden headboard, two bedside lamps, a decorative wreath, and a bed with patterned pillows.

9. The Modern Farm House

The Modern Farm House
Trenton
10.0 out of 10, Exceptional, (9 reviews)
"Just an overnight stay on my way to Branson, but was perfect. I would definitely stay there again and maybe for a longer stay."
United States
Gwen
$166 nightly
The price is $185
Sep 30 - Oct 1
Total with taxes and fees
The Modern Farm House
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 Osgood Hotel Reviews

Spacious 5-bedroom house in pleasant Milan with AC and large screened in patio

Spacious 5-bedroom house in pleasant Milan with AC and large screened in patio

10/10 Excellent
"Great place to stay exactly like descriptions! Very clean and well organized, Everything went smoothly at check in and check out! 10 out of 10 highly recommend!"
Amy M. 4-night trip
Posted 4 days ago
Spacious 5-bedroom house in pleasant Milan with AC and large screened in patio

Find out more about Osgood

Everything you need to know about Osgood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osgood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osgood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osgood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osgood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osgood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osgood rentals

At Expedia, we put the best Osgood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osgood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osgood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osgood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Osgood?

Yes, we offer vacation rentals near well known sights in Osgood, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Osgood?

Spacious 5-bedroom house in pleasant Milan with AC and large screened in patio: This vacation home rental near Osgood is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

What can I see and do in Osgood?

Visit the sights while you're exploring the area such as Gladys Grimes Public Park and Black Silo Winery.

What are vacation rentals like in Osgood?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Osgood. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips.