
Vacation rentals in Medford
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Top-rated vacation rentals in Medford
Guests agree: these stays are highly rated for location, cleanliness, and more.
Unwind at a Luxury Cottage in Jacksonville's Historic Core
Enjoy your stay at "The Laundry" a lovely historic home. Remodeled and professionally decorated in French Country Chic style with luxury Italian Frette sheets, Turkish towels, robes, slippers, enchanting landscaping with two private fountains and outdoor eating! Ample onsite parking with complete privacy! Two flat screen SMART WIFI TV's with Cable and WIFI/Internet provided, desk/work area along with fun games. A washer/dryer with soap supplies is provided for your convenience. A fully stocked kitchen with stainless steel appliances and gas range. Cuisinart coffee pot with Starbucks coffee and tea provided. You will have access to the entire home. Approximately 1250 sq. ft. with high ceilings. For your comfort the bedroom has a large king size BeautyRest Black mattress with feather-bed topper, Italian linens and Hungarian down pillows. The living room has a large deep couch with feather stuffing. Couch is also a Queen size sofa sleeper that can comfortably accommodate 2 adults. We offer self check-in but I live only 5 minutes away from the cottage. We're happy to help answer questions :) This property is in the core of historic Jacksonville, very conveniently located close to quaint shops and restaurants. Explore hiking trails, try wine tasting, and take an easy day trip to Crater Lake National Forest for a nature fix.

Cute Boho w Patio, W/D, Parking (No Chores!)
Top floor of house is all yours with private exterior entrance. The first floor is a separate unit with separate entrance. Fast Wifi + Kitchen + Privacy + Outside Deck! Welcome to our charming, boho unit, nestled on the entire, private second floor of this historic 1937 home. A perfect getaway for couples, small families, and business travelers alike -- private entrance and deck. Explore the scenic Rogue Valley, indulge in local wineries, and enjoy a comfortable stay in this picturesque gem

Angel Crest Casita Guest Suite - East Medford
Enchanting, large, private 1 bedroom guest suite with a view In Upper East Medford. Beautiful, open concept living /dining area has plenty of room to relax and unwind. This space also includes a semi private queen bed. There is a large luxurious shower, kitchenette, and other amenities (microwave, fridge, and coffee maker). Outside there is a large private covered deck with outside seating and a fire pit. Close to wineries, golf, restaurants, and great hiking. This is a non smoking property.

The Greenwood Villa w/wood fire hot tub
The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

The Cutie Little Loft
The Cutie Little Loft is a clean, stylish and centrally located new build. A comfortable bed, a full kitchen with brand new appliances, and extra special little touches, will make your stay easy and enjoyable. Whether your main destination is Medford, or perhaps you plan to visit nearby cities like historic Jacksonville or Ashland, the CLL is a great point of access for all. Numerous restaurants, hiking trails and wineries are nearby allowing an eventful trip to the beautiful Southern Oregon.

Wine Country Farm Stay Near Ashland
Stunning romantic wine getaway on a flower farm with spectacular views. Farm stay offers the perfect base for exploring the Rogue Valley wine trail, 15 minutes to over 20 Jacksonville and Ashland wineries in the heart of the valley. Cozy private deck offers a perfect spot to relax and enjoy wine with views of mountains, pastures, and fields. Home of the Oregon Shakespeare and Britt Festivals. One mile from the Greenway, a bike and pedestrian pathway. Enjoy a beautiful ride to local wineries.

Suite Comice EV Charging
*NOTE*: We disinfect all surfaces before and after new guests arrive. Studio suite with private entrance. Comfortable, light, clean and airy. Host on location in attached home. Breakfast nook with coffee, and tea. Neighborhood is quiet with shopping and dining not far away. Only one small step into the unit. Also on the property is another 2 bedroom Airbnb unit, Comice Valley Inn, in the event you have a larger party. This is a new listing, so please see some of my many 5-star reviews.

The Aloha House - Hot Tub - Pool
The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Southern Oregon Gem (EV Charger)
Welcome to our charming little home in Medford, Oregon. a delightful haven designed for comfort, cleanliness, and efficiency. Nestled near the city center, this inviting space offers a perfect blend of coziness and functionality for a memorable stay. The thoughtful layout maximizes every inch of space, creating a welcoming atmosphere for solo travelers, couples, or small groups. The color palette is soothing, creating a serene ambiance that promotes relaxation.

Cozy Cottage
Discover this charming gem nestled in the heart of Medford, Oregon! This enchanting 1 bedroom with a king bed and 1 bathroom cottage is a centrally located and offers the perfect blend of comfort and style. The sofa in the living room is a hide-a-bed which can sleep 2 additional people. Conveniently located near shopping, restaurants, and more! For the safety and security of our guests, we do have an outdoor camera monitoring common areas.

Eco-Tiny House in SE Medford
Clean and quiet 200 sq ft. detached guesthouse with kitchenette nestled among vegetable gardens and native wildflower beds. Within walking distance of Asante hospital and several shops and restaurants. Easy access to freeway. 20 minutes from downtown Ashland and Jacksonville and only and 10 minutes from downtown Medford. Off-street parking available. Well-behaved pets welcome. Please no smoking inside the guesthouse or on the property.

Charming Two
Your family will be close to everything when you stay at this centrally-located place. Providing a clean and cozy environment. This Airbnb is close to everything and minutes away from Roxyann peak and winery. Close to all hospitals, parks, and located in east Medford. There’s a park 2 blocks away. Great for kids and pets. Safe and large back yard gated for kids and pets.
Popular amenities for Medford vacation rentals
Other great vacation rentals in Medford

Cherry Lane, Crystal Skies

Rural Rest & Celestial Views

Wisteria Garden | 1GB WIFI | Long-Stay Ready

Valley View Escape

Capital House - Private getaway with POOL!

Paschal Winery - Dream 2 Cottage

Home Again Home Again Guest house in E Medford

The Loft
When is the best time to visit Medford?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 CAD | $137 CAD | $137 CAD | $145 CAD | $157 CAD | $175 CAD | $174 CAD | $161 CAD | $163 CAD | $164 CAD | $149 CAD | $156 CAD |
| Avg. temp | 5 °C | 7 °C | 9 °C | 12 °C | 16 °C | 19 °C | 24 °C | 24 °C | 20 °C | 13 °C | 7 °C | 4 °C |
Frequently Asked Questions
What are the best places to stay in Medford?
Downtown Medford is often suggested for easy access to restaurants, shops, and tasting rooms. Residential neighborhoods near parks and green spaces also provide convenient stays for a quieter experience.
What are the best things to do in Medford with kids?
Families can explore science exhibits at Kid Time Children's Museum, play in local parks, or enjoy the Bear Creek Greenway. Seasonal fruit picking at nearby orchards is frequently suggested for a hands-on experience.
What are some of the best things to do in Medford?
Explore tasting rooms downtown, hike Roxy Ann Peak, or stroll the Bear Creek Greenway. Visitors also enjoy local theater, public art installations, and farm-to-table dining.
How is the weather in Medford?
Medford has cool, rainy winters around 33–48°F (0–9°C) and warm, dry summers reaching 91–92°F (33°C). Spring and fall bring mild temperatures with changing foliage and blossoming fruit trees.
When is the best time to visit Medford?
Late spring through early fall is often recommended, with warm afternoons around 75–92°F (24–33°C) and fewer rainy days. These months feature blooming landscapes and local festivals.
What are the best places to visit in Medford?
The Harry & David store, Roxy Ann Peak, and Bear Creek Park are often recommended for local flavor and outdoor recreation. Downtown Medford has tasting rooms, regional shops, and historic architecture.
What are some hiking trails in Medford?
Roxy Ann Peak’s Prescott Park has scenic trails with valley views. The Bear Creek Greenway is frequently suggested for paved walking, biking, and nature observation.
What are some family activities we can do in Medford?
Visit Kid Time Children's Museum for hands-on exhibits, play at Bear Creek Park, or participate in seasonal fruit picking at local orchards. The Rogue Air Trampoline Park and public pool facilities are also family favorites.
What are some of the best day trip ideas from Medford?
Explore Crater Lake National Park’s scenic highlights, discover quaint towns known for artisanal shops, or hike among waterfalls in the Rogue River area. The surrounding region is also noted for vineyards and farm tours.
Are there any pet friendly accommodations available in Medford?
Many vacation rentals in central and residential Medford neighborhoods welcome pets. Parks like Bear Creek Park make it easier to explore outdoor spaces with your companion animal.
What are some local tips for visiting Medford?
Locals suggest checking the outdoor concert schedule and wearing comfortable shoes for markets or nature paths. Exploring the Rogue Valley's wineries or stopping for seasonal fruit at roadside stands is frequently suggested.
What is Medford known for?
Medford is known for its agricultural heritage, especially pear orchards and local vineyards. The city has access to the Rogue Valley’s outdoor spaces, and is a hub for exploring Southern Oregon’s culinary and cultural experiences.
What are the best hidden gems to explore in Medford?
Locals enjoy the outdoor art walks, community murals, and browsing historic buildings in smaller downtown blocks. Neighborhood bakeries and family-run food trucks showcase distinct flavors of the Rogue Valley.
What are the best foods to try in Medford?
Sample locally grown pears, fresh berries, and seasonal produce from farmers markets. Medford also has craft cideries, bakeries known for marionberry desserts, and a range of global cuisine reflecting the area's diverse community.
What should I bring for a trip to Medford?
Pack layers to adjust to Medford’s shifting temperatures and bring sun protection for summer visits, as afternoons can reach 90°F (33°C). A rain jacket is useful in winter and spring, and comfortable shoes help for exploring parks, markets, and trails.
What is the nightlife in Medford like?
Medford’s nightlife has casual pubs, local breweries, and venues for live music around downtown. Wine bars and theaters showcase regional artists and events throughout the year.
What are the most popular events or festivals in Medford?
The Pear Blossom Festival in spring is often recommended, celebrating local agriculture with parades, food, and community activities. Summer and fall weekends also bring outdoor concerts and farmers markets.
Are there family friendly vacation rentals in Medford?
You’ll find family friendly vacation rentals in Medford’s residential neighborhoods and near green spaces. Many homes have amenities like kitchens, multiple bedrooms, and outdoor seating areas to accommodate groups.
Quick stats about vacation rentals in Medford

Total vacation rentals
Explore 380 vacation rentals in Medford

Nightly prices starting at
Medford vacation rentals start at $27 CAD per night before taxes and fees

Verified guest reviews
Over 33,850 verified reviews to help you choose

Family-friendly vacation rentals
190 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 170 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wifi availability
370 of Medford vacation rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Medford rentals

4.8 Average rating
Medford stays are highly rated by guests—averaging 4.8 out of 5!
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