Vacation rentals in Midland

4.98 out of 5 average rating, 492 reviews

A bright living area features a comfortable white sofa and a small round table. Large sliding glass doors lead to an outdoor deck surrounded by trees. Natural light fills the space, highlighting the warm wood tones of the flooring and ceiling.

Guesthouse in Ashland

Charming cottage, walk to town.

JulieRating, 5 stars2 weeks ago

There aren’t enough adjectives for how charming Margaret’s cottage is. From the location, to the quality of the cottage, and the little touches that mean so much. Radiant floor in the downstairs bathroom, gorgeous kitchen, and high vaulted ceiling. I felt right at home when I walked through the door. The upstairs loft bedroom with king bed was so comfortable, and the adjacent upstairs 1/2 bath made things very convenient. I felt like I was in a treehouse and slept so peacefully every night. Margaret is always available if you need anything, otherwise the place is completely your own to relax. I will always remember this place as I spent the last week of my work career in her cottage, and the first few days of being retired. This charming Ashland cottage was the perfect place to transition. I look forward to going back! Thank you Margaret for your kindness, hospitality and sharing your home. 🙏

Superhost

The exterior of a two-story green house is displayed, featuring a central entrance door framed by white trim. Colorful red foliage from nearby trees enhances the welcoming atmosphere. A clear blue sky provides a bright backdrop to the well-maintained landscaping.

Home in Ashland

4.81 out of 5 average rating, 120 reviews

Street Level Flat in great Downtown Location "A"

CherylRating, 5 stars1 week ago

Lovely home, great location, great host. One thing to be aware of is that the home is actually a duplex, with people staying up above you. If you are noise sensitive, the sound of people walking, moving chairs, staying up could bother you. We were fine because we normally use earplugs at night, but just something to be aware of.

5 out of 5 average rating, 118 reviews

The entrance to Willow Tree Ranch is lined with trees, leading toward a spacious blue building set against a clear sky. The driveway is paved and surrounded by fallen leaves, with a fence marking the perimeter.

Ranch in Klamath Falls

Mod. Barndo on Peaceful 100 Acre Ranch w/ Hot Tub

AndreaRating, 5 stars4 days ago

We absolutely loved our stay here! The ranch was a wonderful retreat. It was beautifully appointed and had everything we needed and so much more! I wish we could have stayed longer - that kitchen was phenomenal and would have been great to get more use out of. The decor was homey and well thought out. The bed was incredibly comfortable! Will absolutely stay here again if in town, and would recommend this spot to anyone!

4.96 out of 5 average rating, 189 reviews

A serene lake view features a group of white pelicans gathered on the water's surface, surrounded by lush greenery and rolling hills in the background. The calmness of the scene is enhanced by a clear blue sky dotted with soft, white clouds.

Home in Klamath Falls

Lakeside Living & All Day Bird Watching

IvanRating, 5 stars5 months ago

Met friends from California and Washington in Klamath Falls to ride Spence and Moore, house is 1mile from Moore, and 9 miles from Spence. The house has a great fenced backyard with bbq and propane heater. Great location 1.5 miles from downtown.

The living area features a sleek black entertainment unit with a flat-screen television displaying a serene landscape. A potted plant adds a touch of greenery, while light hardwood flooring complements the bright white walls. An adjacent doorway leads to another space in the home.

4.88 out of 5 average rating, 325 reviews

Southern Oregon Gem (EV Charger)

LincolnRating, 5 stars2 days ago

Great roomy space. Other than it being a very tight bathroom, there's is plenty of room for several large adults. Spacious main bedroom, decent second bedroom, comfy long sectional. Idealy for 3 adults in my mind. Very convenient location, easy access, parking. If you're on the fence, and fine with 1 bath, just book it.

An outdoor patio area features a built-in gas grill and a wraparound sectional seating arrangement. A circular fire pit is positioned nearby, with string lights hanging above the space. The surrounding wooden fence provides privacy, enhancing the cozy atmosphere.

4.95 out of 5 average rating, 109 reviews

Voted Guest Favorite/Fast Wi-Fi/Hiking/Shopping.

KatieRating, 5 stars1 month ago

We had a last minute booking due to a plumbing issue with our original stay. Jessica was able To quickly get us in, was responsive and easy to work with. House was clean, had the amenities we needed and met our needs. Thank you!

4.97 out of 5 average rating, 115 reviews

A charming cabin is nestled among tall fir and pine trees, with a pathway leading to a welcoming entrance. Soft lighting enhances the inviting facade, while large windows reveal a glimpse of the interior. A kayak is positioned nearby, adding a touch of outdoor adventure.

Cabin in Klamath Falls

A clean, well-appointed cabin in Rocky Point!

LeonardoRating, 5 stars1 month ago

This is the best place me and my family have ever stayed in the cabin was extremely clean which was impressive because they accept pets! Tammy provide everything a cabin should have its cozy comfortable all they above definitely made the stay 100% better

4.99 out of 5 average rating, 179 reviews

An outdoor dining area features a square table with a polished wooden top surrounded by four metal chairs. A decorative lantern sits at the center of the table. Lush greenery and colorful flowering plants are positioned nearby against a slatted privacy fence.

Guesthouse in Ashland

Courtside Cottage - WalkScore 93 - Dog Friendly

MichelleRating, 5 stars1 day ago

We just had a quick overnight stay but it was perfect for us. The bed was super comfy, which is important to me. The shades get the room dark enough to sleep in! The thermostat works great. It was really a lovely little space in a perfect location close to everything. I’d highly recommend this place. My husband and I were there with our daughter, who slept on a very nice bed from the pullout sofa. We didn’t use the kitchen or shower but they looked nice.

5 out of 5 average rating, 9 reviews

A serene outdoor space is displayed, featuring well-maintained green grass beneath a large tree. A circular table with chairs is positioned under an umbrella, overlooking expansive views of the valley and distant hills.

Villa in Ashland

Ashland French Country Villa w/ Spectacular Views

NathanRating, 5 stars6 months ago

This is such a lovely place. Top notch greeting from the host at the beginning of our stay and then total privacy the rest of the time. Incredible views and very well appointed home. Sharp knives, plenty of cooking utensils and anything you can imagine to host family and friends. The beds were like clouds with soft duvets and plentiful pillows. The boys had so much fun learning the art of billiards in the spacious living room full of panoramic views. After exploring all that Ashland has to offer, this property was exquisite to come home to every night. We wanted more time.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Midland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Midland

An outdoor patio is featured with four wooden Adirondack chairs arranged around a gas fire pit table. A ceiling fan hangs overhead, and the space includes a neatly maintained grass area enclosed by a wooden fence, providing privacy.

5 out of 5 average rating, 51 reviews

Home Away From Home

LicaRating, 5 stars4 months ago

We had a great stay, the best vaca rental experience to date. Lovely house, incredibly clean and well maintained, welcoming and comfortable, exactly as described and pictured, and Debbie and James were wonderful hosts. We were in Medford to visit family for the holidays, and the house was a lovely place to relax after a long day of festivities (I love my family, but you know LOL). Thank you so much Debbie and James!

Superhost

The kitchen features light wood cabinetry and an island with seating for three. Stainless steel appliances include a stove and oven. A large window allows natural light to fill the space, and a trash can is positioned beside the island.

Home in Klamath Falls

4.78 out of 5 average rating, 9 reviews

Your home away from home

MichaelRating, 5 stars4 months ago

A nice house, very clean and well appointed. The stocked coffee bar was great. A TV in every room, and the bathrooms stocked with needed items.

Superhost

Home in Chiloquin

4.8 out of 5 average rating, 41 reviews

Agency Lake House

DannyRating, 5 stars4 months ago

Brad and Trish were wonderful hosts and very responsive. Brad would often give us fresh eggs! The location was beautiful and peaceful, close to crater lake.

5 out of 5 average rating, 9 reviews

Home in Phoenix

Historic Farm Estate | Countryside Haven | Ashland

Sarah And AndrewRating, 5 stars7 months ago

Our big family was able to have a wonderful stay. Lots to do in Ashland and hanging at the house was so nice. We cooked, we sat outside and at the big dining table. Everyone had their own space too. The house is beautiful and decor funky and cool. We’d love to stay again!

4.95 out of 5 average rating, 111 reviews

A spacious bathtub is featured with a smooth, molded design. Decorative elements include a large wall mural depicting a coastal scene with waves, enhancing the serene environment. Fixtures are positioned for easy access, and the surrounding wall is painted in a neutral tone.

Home in Bonanza

Little's Hideaway

ZulemaRating, 5 stars7 months ago

Chris place is nice and very clean is very quiet so we can rest during nights, has everything for cooking your meals so we just feel at home.

A view from an open door reveals a vibrant blue pool surrounded by a wooden deck. A bar table and stools are positioned nearby under an orange umbrella, while a patterned outdoor rug adds color to the scene.

5 out of 5 average rating, 35 reviews

Holly Street House

PatsyRating, 5 stars1 month ago

We really enjoyed our stay at Daniel and Shereen’s place. Loved the wine, treats and flowers left for us. They were very responsive to any questions or concerns.. the home had plenty to do. Loved the fireplace and hot tub with a private backyard. The only drawback I could possibly find was no area really for dogs to use in the backyard, but made it work with the front yard. Just had to keep her on a leash. I thought the sign in book was a fantastic touch for visitors to write in. First place I had seen that. Would definitely stay here in the future!

4.96 out of 5 average rating, 108 reviews

Home in Prospect

Ripple Rock Ranch Lodge

LauraRating, 5 stars2 weeks ago

We wanted a place to stay that had private areas since it was two couples but also a nice gathering area for the four of us. This was the Perfect Place! The open Kitchen, dining and living area were quite large with comfortable seating for all of us. The deck on the back of the house was perfect for afternoon cocktails while watching the sunset and the river with all the beautiful wildlife. We found that Shady Cove which is only a 20 minute drive had a nice grocery store and several restaurants. The drive to Crater Lake was about an hour and was absolutely spectacular even in the early spring. We also took advantage of fishing while we were there on the river. FYI check with a fly Shop to make sure you have your rig set up correctly because the police do stop and check for fishing license and your Line length. I would absolutely stay here again and it is the perfect place to relax after a day at Crater Lake.