Family Vacation Critic Favorite


2520 Ashland Street, Ashland, 97520, OR

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1 Room / 2 Adults

1 rooms,
2 adults
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Editor's Rating


When you first drive up to the BEST WESTERN Windsor Inn, you may think you’ve traveled back in time to 15th century England and the age of Queen Elizabeth and William Shakespeare. Well, maybe not, but the mock Tudor architecture of the hotel is fun, and will almost certainly put you in the right mood for the Shakespeare Festival in downtown Ashland, Oregon. The Windsor’s location right off Interstate 5 makes it easy to find, but it’s situated far enough off the freeway that you don’t hear the traffic noise.

One of the first things you notice before entering the lobby is the lush landscaping all along the front of the main building, These English gardens continue the Shakespearean theme and provide a nice buffer between the hotel and the parking lot. The neatly clipped hedges, leafy trees, and twisty topiaries are accented by dozens of gorgeous rose bushes and other flowering shrubs. It’s all lovely to look at, either from the window of your room, or while eating pancakes each morning in the hotel’s breakfast room.

The Windsor staff is friendly and helpful, greeting our kids directly and offering a plate of freshly-baked chocolate chip cookies. During our visit, they were also quick to point out the swimming pool and its hours, knowing this is the most important thing to any child.

Beyond the lobby, you’ll find two floors of spacious rooms for families both large and small. The rooms, some with balconies, are clean and roomy, so a big family won’t feel squeezed for space. There are suite options that feature king beds and sleeper sofas, with room for a few sleeping bags. Most of the suites have a kitchenette, which can help you save money at meal times.

Our Editor Loves

  • Huge outdoor pool
  • Spacious family suites
  • Free shuttle service to downtown

Family Amenities

  • Family Room 5+
  • Free Breakfast
  • Free Wi-Fi
  • Kitchenettes
  • Laundry
  • Pool
  • Refrigerator

Room Information

Find the Best Price for Your Stay

Standard Rooms
The most economical choice at the Windsor Inn is their standard room, which can hold a small family of three or four. You'll get a spacious room with two queen beds. Ours had a double sink vanity situated outside of the shower/toilet, which works wonders when everyone is trying to brush teeth and get ready to go in the morning. These rooms also have basic amenities like a microwave, refrigerator, ironing board, and hair dryer. We were expecting the Shakespeare/Tudor decor to continue into the rooms, but instead found Oregon-themed pictures and paintings, along with new carpet and furniture, including a small round table and two comfy chairs.

All of the rooms at the Windsor are incredibly quiet. We never heard a peep from our neighbors, and the nearby pool closed down at 10 p.m. so there weren't any kids shrieking and splashing late into the night. There are two floors of rooms, spread out around the parking lot in a large L shape. Rooms on the upper floors have high ceilings, making the space seem much bigger and less stuffy.

Suites at the Windsor Inn are huge, but only come with king beds in a separate room. In the living area, you'll find a sleeper sofa. Ask the hotel for a rollaway bed as well, and a family of four or five can sleep comfortably. Suites also come with kitchenettes stocked with pots and pans. As with the standard rooms, everything looks and feels new after the recent remodel. Fresh, smart decor can make you feel as if you're in a luxury hotel. The huge amount of space in each suite just adds to the feeling that you're getting more than what you're paying for.

Our favorite feature of each suite was the counter area separating the kitchenette from the living area. Two padded stools, along with the table and chairs, allows for plenty of eating area for the whole family if you're having a meal in your suite. The double vanity sinks are a nice touch for keeping families from crowding each other in the morning rush to get ready. Ask for a second-floor suite in the Garden Wing of the hotel for the ultimate quiet.


Consistently great property!

by lilcarlover

Nice layout with attractive grounds. Helpful, friendly staff and a great selection for breakfast. Can be a bit pricy depending on time of year but not too bad. Conveniently located about 2 blocks off Interstate 5 on the outskirts of Oregon's coolest town, Ashland.

Average Room, Friendly Staff but Convenient to I-5

by speninosmith

This hotel is a couple miles outside of town; so don't plan on walking. However, after a 5 minute drive, on is in the center of things. The rooms are clean, recently refurbished but nothing to write home about. However, the hotel is quite convenient to the interstate
and, surprisingly quiet. The front office staff is extremely friendly and helpful.

Family Activities

When you arrive at a hotel, there's nothing more exciting for kids than seeing a pool. Just wait until they find out the Windsor Inn has the largest outdoor pool in all of Southern Oregon! Granted, it's not some huge Olympic-sized body of water, but it's still quite roomy by most hotel standards. This means that parents and older teens can swim laps without constantly bumping into the younger kids splashing and playing.

The pool area is set in the farthest corner of the property from the street, isolating it from traffic noise and public activity. There's plenty of deck space around the pool for families to grab a few lounge chairs and set up a little base of operations. Parents will love stretching out to relax without feeling like they're right on top of the pool. Part of the deck area is shaded by the hotel wing on one side, but there are also tables with umbrellas along the fence. Landscaping all around the enclosed area completes what is one of the better pools we've seen in a hotel of this size. The hot tub next to the pool is similarly large, big enough to hold several dozen guests, with elbow room to spare. The hotel provides plenty of clean towels at poolside. Hours for both pool and hot tub are 7 a.m. to 10 p.m.

Family Dining

The only onsite dining at the Windsor Inn is the free buffet breakfast served each morning in the bright and airy breakfast room that looks out on the English gardens. It's a standard serve-yourself offering, but a cut above the typical continental breakfast. Highlights include a pancake-making machine, which is always fascinating for kids, biscuits and gravy, sausage, fruit, yogurt, toast, and cereal. It's plenty to give the kids enough energy to start a busy day.

For something more substantial, guests only have to walk across the hotel parking lot to the adjoining Oak Tree Northwest Bar and Grill. They serve a hearty breakfast that includes huge omelets, stacks of pancakes, and very tasty eggs benedict. The Oak Tree is also convenient for lunch and dinner if you don't want to stray far from the hotel.

For a night in your room, or even relaxing by the pool, call the nearby Great American Pizza Company if you want a good pizza delivered. However, our recommendation is that you hop in your car and make the 5-minute drive to Martolli's Handmade Pizza for a carryout order of the absolutely best pizza in Ashland. They have two locations in town, so you'll want to hit the closest one across from Southern Oregon University. Unfortunately, they don't deliver anymore, but it will be worth it to your family to go get it yourself. Their pizzas are all freshly made, and they also have huge salads and calzones. Makes for an awesome pool party back at the hotel.

In-Room Dining
Some suites at the Windsor Inn contain a kitchenette stocked with pots and pans, so you might want to stock up on groceries at the nearby Albertson's grocery store, a full-service supermarket less than half a mile away. If you're looking to buy local, pay a visit to the downtown Ashland Food Co-Op for a full selection of natural and organic foods, either grown or produced locally. They also have an outstanding deli where you can pick up gluten-free and vegan sandwiches to take back to your room.

Planning & Tips

All About the Extras
Wi-Fi is strong throughout the resort, so your teens will be happy.

Fitness Center
The hotel has a large exercise room, with big bright windows looking out on the gardens. The equipment is a bit dated, but does the job if you need to get your workout done.

The Windsor Inn is extremely pet-friendly. Staff even hand out a little doggy treat bag at check-in. Be warned, however, that there is a $20 fee to accommodate pets in your room.

Check-in time is 3pm, while check-out is 11am.

The Art of Smart Timing
Ashland, Oregon is a popular destination almost all year long. The Shakespeare Festival is the main draw during the area's eight-month season, which lasts from February through November. The town gets slightly more crowded during the summer months, as outdoor enthusiasts take advantage of the surrounding rivers and mountains. Even though there seem to be plenty of accommodations in town, they still book up far in advance as people plan their vacations around the festival's schedule of performances each year. As a high-quality budget-friendly hotel, the Windsor Inn is going to be one of those hotels that sells out early in the season. You'll want to plan ahead to get the ideal room for your family.

Getting There
Ashland is located on the southwestern edge of Oregon, near the California border. It is easily accessible by Interstate 5, which runs north-south from Washington to California. The closest large urban area is Portland, Oregon to the north. From there, you can reach Ashland via I-5 in about four hours. If you are flying in, the Rogue Valley International Airport is a mere 16 miles away in the town of Medford. The Windsor Inn is conveniently located on the east side of the Interstate, just off Exit 14, about three and a half miles from the Shakespeare Festival.

Getting Around
Ashland, Oregon is a small town. Its downtown area is quite compact, with shops and restaurants mostly clustered along Main Street within walking distance of the Shakespeare Festival. The Windsor Inn is located just over 3 miles from the downtown area. One of the nicest perks of staying at the Windsor is their free shuttle service that runs during most of the festival season. It is so nice to not have to worry about the parking situation downtown. The shuttle runs throughout the day and late into the night, as is needed for theatre productions. Ashland is also a classic bicycle town, so look to rent bikes for the whole family to make getting around even easier.

By far, the biggest perk of the Windsor is its free shuttle to downtown and the Shakespeare Festival. It was such a relief to leave the car at the hotel and not worry about finding a parking spot. At check-in, be sure to alert the front desk that you will want to make use of the shuttle during your stay. They'll let you know how it works, what hours it runs, and where to board.

For Mom and Dad
The Windsor Inn's pool and hot tub area are a great place for parents to find a little freedom to relax. Tuck the kids into bed early and sneak down to the sizable hot tub, which is open until 10 p.m., where you're likely to find a few other moms and dads.

You might also try the Caldera Brewery and Restaurant, a 5-minute walk from the Windsor Inn, for over 40 different kinds of craft beer and a full menu of pub food. The atmosphere is fun and casual, especially on the outdoor patio at sunset. Plus, where else can you see the state's largest collection of beer cans and bottles?