Online travel agent Daniel Perry manages 100 vacation rentals in Ashland, from a single room to an entire house, where a chef can be hired to make meals. We asked the owner of BookStayHop to suggest a home stay for various Ashland visitors, from singles and couples to large groups.

Many of the vacation rentals are in Ashland’s downtown area, which allows out-of-towners to leave a car behind and live like a local, says Perry.

Airbnb, Vrbo and other home stay businesses are legal here and a very high number – 80% – are in compliance and pay lodging taxes, says Travel Ashland director Katharine Cato.

For more tips, read the just published Ashland Insider’s Guide with well-known and hidden spots to eat as well as ways to enjoy Oregon Shakespeare Festival events on a budget and where to park when everyone’s downtown.

The first of Perry’s 10 suggestions is Lori Lane House, which is five blocks from downtown Ashland. The newly remodeled, two-story allows a large group to spread out among the dining, sitting and relaxing areas or on the patio. The Juliet Cottage can also be rented for four more guests.

Details:

• Accommodates 10 guests

• Five bedrooms

• 3.5 bathrooms

• Around $575 a night on average, depending on travel dates

More info

The renovated, 1900s Blue Moon House & Cottage sits in one of Ashland’s historic neighborhoods and is five blocks from the Oregon Shakespeare Festival campus.

The house has a living area with a fireplace, gourmet kitchen with a large dining area, and five bedrooms, each with a private bathroom. A large deck overlooks the garden and a cottage.

Details:

• Accommodates 15 guests

• Six bedrooms

• Six bathrooms

• Around $800 a night on average, depending on travel dates

More info

The pet-friendly Courtside Cottage is a five-minute walk from OSF theaters and Ashland’s downtown shops, restaurants and bars. The vacation rental is near the popular Growler Guys tap house at 345 Lithia Way and a two-minute walk to legendary Bloomsbury Books at 290 E. Main St.

The cottage is on a very quiet residential street has been fully remodeled.

Details:

• Accommodates four guests

• One bedroom

• One bathroom

• Around $195 a night on average, depending on travel dates

More info

The modern, two-story Spur Rail Loft House in the Historic Railroad District a few blocks from downtown is designed for a weekend away or an extended stay.

Relax in the large living room near the fireplace and on the private patio.

Stock the kitchen with organic provisions from the famous Ashland Food Co-op at 237 N. 1st St. Best-selling author Cheryl Strayed found comfort and friendship at the co-op and described it in her memoir, “Wild: From Lost to Found on the Pacific Crest Trail."

Details:

• Accommodates six guests

• Three bedrooms

• Two bathrooms

• Around $195 a night on average, depending on travel dates

More info

'C' Street Station studio in a quiet neighborhood in the Historic Railroad District is a 10-minute stroll to downtown and OSF theaters.

The covered patio has an al fresco dining area and barbecue.

Details:

• Accommodates two guests

• One bedroom

• One bathroom

• Around $149 a night on average, depending on travel dates

More info

The two-story Pioneer Craftsman House was built in 2008 and shares the property with a historic home and another dwelling one block from OSF theaters and near downtown dining, wine tasting and shopping.

Enjoy quiet time in the jetted hot tub or on the second-floor balcony or lower patio.

Details:

• Accommodates eight guests

• Three bedrooms

• Two bathrooms

• Around $163 a night on average, depending on travel dates

More info

The Aloha House hilltop retreat has large windows, vaulted ceilings and skylights to frame vista views.

The property in a forested neighborhood sits above Southern Oregon University and just 1.5 miles from downtown Ashland’s crown jewel, Lithia Park, which was named one of 10 Great Public Spaces in America.

Two separate studios are connected by an outdoor living space with a dining area, swim-jet pool, bar, spa and outdoor shower.

Each studio has areas to relax, sleep and bathe (one has a spa tub and sauna and the other has a shower).

Details:

• Accommodates four guests

• Two bedrooms

• Two bathrooms

• Around $225 a night on average, depending on travel dates

More info

Paschal Winery’s Dream Cottage, on vineyard property with a tasting room, is tucked in the eastern hills between Ashland and Talent to the north.

The bungalow has 850 square feet of living space. Slide open the new barn doors to see the bedroom and spa-like bathroom.

Details:

• Accommodates four guests

• One bedroom

• One bathroom

• Around $184 a night on average, depending on travel dates

More info

The Wine Suite at Rellik Winery & Alpaca Farm is in historic Jacksonville, just 1.5 miles from the grounds of the mini Hollywood Bowl-like Britt Music & Arts Festival, in the center of Southern Oregon Wine Country and a scenic, 30-minute drive from Ashland.

The 700-square-foot home rests in a country setting near a tasting room pouring estate wines from grapes grown across 15 acres that are shared by the winery’s resident alpacas and llamas.

A fire pit with comfortable outdoor seating and a swimming pool are shared by all the guests.

Details:

• Accommodates four guests

• One bedroom

• One bathroom

• Around $136 a night on average, depending on travel dates

More info

Active people who like to hike in the spring, raft in the summer, take in fall’s bronzy scenery or play in winter snow escape to Hyatt Lake 18 miles east of downtown Ashland.

#51 The Cabins at Hyatt Lake has an electric fireplace, barbecue, hot tub and lake views.

Details:

• Accommodates six guests

• Two bedrooms

• One bathroom

• Around $155 a night on average, depending on travel dates

More info

Looking for more ideas?

Dozens of Oregon getaways let you soak in natural hot springs: Ease into the new year by soaking the day away at Crane Hot Springs, a getaway off Oregon Route 78 east of Burns that The Oregonian/OregonLive travel writer Jamie Hale calls “an oasis.”

If you're too relaxed to leave a cedar tub bubbling with mineral water from natural hot springs ($15 an hour) or the soothing, 101-degree pool ($10 for four hours), stay overnight inside a rustic room or tepee, or set up a tent or park your RV at one of the campsites.

Perhaps you'd like to explore beyond the remote resort? The slow winter season in southeast Oregon's high desert will allow time to learn about the area's fascinating prehistoric history and other places to soak.

Here are different ways to stay in Harney County.

Escape to one of Oregon’s wacky, funky, adorable getaways for rent like this quaint, solar-powered cabin near Vancouver.

Getaways mean more than staying in a different shelter. Vacations are supposed to be physical and mental escapes from real life.

If you truly want an experience that's unlike the place you lay your head, check out Oregon's wacky, funky, adorable lodging, from a Swiss Family Robinson luxury tree resort to an off-the-grid yurt.

How about sleeping in a teepee on a yak ranch in Bend?

In this week’s home stay gallery, we check out 10 oddball abodes that you can check into.

10 cozy, cool, crazy cabin vacation getaways: Escape to Oregon mountains and lakes or the California desert

The need to be in nature may be strong, but there are so many ways to relax amid towering trees in the mountains or next to a lake.

In this week's vacation getaway roundup, we look at cabins of all kinds, from a classic A-frame in a forest to a modern dwelling in the desert.

Rustic or luxury? Cozy or expansive? It’s up to you to decide: Are you dreaming of a romantic escape or group reunion?

10 glamorous historic mansions and homes for rent: Are you curious about what luxury looked like a century ago and how it feels today? In this week’s home stay getaway gallery, we peek into 10 historic mansions and homes that you can rent for a day or longer.

Modern kitchen appliances including a fridge mean you won’t have to call the iceman or bring in wood to start the stove. Instead, cuddle into a wingback chair by the fireplace and read a classic.

Bend ranks 4th in U.S. as a vacation rental hot spot. Here are 10 getaways, from funky to fancy: Bend residents may feel as if at least one person in their neighbor is renting out a room or a whole house to tourists. And they may be right.

A study released Wednesday found that Bend has 1,658 Airbnb listings per 50,000 people, which vaults the city on the Deschutes River to the fourth most saturated vacation rental market among more than 750 U.S. cities, according to IPX1031, an investment property exchange service.

When active home rental listings were compared to the population, three Florida cities took top place: Miami Beach came in first with 3,416 listings per 50,000 people. Kissimme, near the Walt Disney World Resort, came in second with 2,880 listings per 50,000 residents and third-place Sarasota, on Florida’s Gulf Coast, has 2,234 listings per 50,000 people.

Across the continent in Bend, there are places to rent through Airbnb, Vacasa or VRBO near the river and close to downtown, from massive estates to tiny houses.

10 snowy getaways near Crater Lake get you close to free ranger tours: Are you ready to be whisked off on snowshoes to explore corners of Crater Lake? Rangers offer free tours and equipment, but you’ll need to get there first since the Crater Lake Lodge and all park campgrounds are closed until late May.

There are winter lodging options near and far like Diamond Lake Resort. Here are 10 snowy getaways.

The entrance road to park headquarters and Rim Village usually remains open year-round, and a discounted $15 entrance fee allows you to explore on your own or go on a free ranger-led snowshoe tour, says Oregonian/OregonLive travel writer Jamie Hale. For tour dates, visit nps.gov/crla or call 541-594-3000.

10 vacation getaways to join Mount Hood’s New Year’s Eve parties: Are you searching for a memorable way to watch the dawn of a new decade? How about ringing in 2020 from Oregon’s tallest mountain?

All three of Mount Hood's major ski resorts -- Mt. Hood Meadows, Mt. Hood Skibowl and Timberline Lodge -- host New Year's Eve parties, each with night skiing, entertainment, food and fireworks, reports Oregonian/OregonLive travel writer Jamie Hale.

In this week’s vacation roundup, we look at 10 different ways to stay near the slopes, from a luxury chalet to a ski-in cabin.

10 accessible Airbnb rentals in Portland, Palm Springs and London: Srin Madipalli is a devoted world traveler who uses a wheelchair. To make it easier to find accessible lodging when booking online, he co-created Accomable, an online resource that was acquired by Airbnb in 2017.

Since then, Madipalli, who heads Airbnb's accessibility team, has refined the homestay rental company's search filters to help people with disabilities and their families find places that can be easily enjoyed without steps or stairs, and other accommodations.

“No two people with a disability are the same, so we offer 27 accessibility filters for a spectrum of needs, and we’re working on more,” says Madipalli.

Where to stay for Willamette Valley’s Wine Country Thanksgiving: From a tiny house to vineyard villa

Thanksgiving weekend in Oregon's wine-growing regions is an action-packed chance for patrons of pinot noir and other varietals to barrel taste this year's vintage as flavors mature and to enjoy food pairings with bottles that have been released (and perhaps are on sale).

More than 140 Willamette Valley wineries will host events in tasting rooms and cellars during Wine Country Thanksgiving, Friday, Nov. 29, through Sunday, Dec. 1.

After stops at scenic vineyards to swirl, sniff and sip, you might want to stay over a night or two. Here are 10 vacation homes for rent, from a tiny abode to a contemporary villa.

10 cool treehouses: These elevated vacation getaways are for rent

Do we really ever grow out of wanting a treehouse? A vacation rental might answer that question.

In this week's getaway roundup, we look at 10 vacation rentals, near and far, designed to elevate your point of view.

These modern dwellings in mostly remote forests are perfect perches for birdwatchers and nature lovers, but they're not always easy to reach. They're rustic and may offer waterfront views but not indoor running water.

What unifies them? They’re cozy.

Airbnb picks the West Coast’s top destination, and it’s Eugene: These are the most wish-listed rentals Of Airbnb’s more than 7 million homestays scattered across the world, which West Coast city rose to the top as a destination more people want to visit in 2020?

Eugene.

The reasons? Travelers like to be around nature and big events, says the lodging company. Green-thinking Eugene has both hiking trails and the University of Oregon’s constant activities.

10 luxury home rentals let you dream big on vacation: Vacations are supposed to be a fantasy come true. Yet, most of us stick somewhat to a budget. But ... we can dream.

Here are 10 luxury home rentals that cost more for one day than most people's monthly housing expenses. Still, there's something appealing about looking at perfect scenery from a secluded perch surrounded by nature and deluxe perks (yes, a butler).

In time for holiday giving – or making plans for a wedding or family reunion – we spotlight off-the-charts, Neiman Marcus fantasy gift level of getaways to rent, in Oregon and once-in-a-lifetime, fabulous destinations.

10 Oregon coast getaways to enjoy a Victorian-style Christmas at the Heceta Head Lighthouse: Lighthouses are a beacon to captains and people curious about these rare, old navigational towers.

If you've never gazed out to sea from a 200-foot-tall vantage point at night, here's your chance: You can enter the Heceta Head Lightstation on Oregon's central coast during the 24th Annual Victorian Christmas Open House from 4 p.m.-7 p.m. on Dec. 7, 8, 14 and 15.

The festive event starts at the Heceta Lighthouse B&B, in the 125-year-old Queen Anne-style keeper's quarters, which is decorated for the holidays. Santa Claus, music and goodies will fill the scene.

Bundle up and stay overnight. Here are 10 vacation homes for rent, from a vintage Airstream to a contemporary house, near Florence and Yachats.

10 spirited vacation rentals to stay in St. Helens as HalloweenTown takes over

Portland is only 30 miles south of St. Helens, making day-tripping easy. But during the October-long Spirit of HalloweenTown festival, which starts Saturday, Oct. 5, visitors may want to linger into the chill of the night, when costumed characters re-enact scenes from movies filmed here, like the "Twilight" vampire saga and the bewitching "HalloweenTown."

Visitors will also learn about space alien invasions and see creepy stuff in the Museum of Peculiarities & Oddities.

The festival is packed with lively activities and most fans know to book lodging early, says Tina Curry of Discover Columbia County. But there are still offbeat and conventional places to stay if you want to join the nightly ghostly walk.

Tiny new cabin in the Mount Adams Outpost: Getaway has tiny cabins in nature to rent outside of Portland as well as Los Angeles, New York City, Washington D.C., Boston, Atlanta, Pittsburgh and Cleveland.

The Mount Adams Outpost is an 80-acre property with handcrafted, dog-friendly hideaways for two to four people. Each one has a fire pit, grilling grate and a picnic table.

Inside the 140 to 200 square feet of living space are either one or two queen-size beds plus a mini kitchen, electric toilet, shower and a cellphone lockbox.

Details:

• Cabin that accommodates two to four guests

• $99-$209 a night depending on travel dates

More info

Here are 10 ideal Airbnb rentals for sweet Cannon Beach getaways: For people who dream of having a beach house, an Oregon Coast vacation rental is a sweet substitute.

In addition to hotels and B&B, Cannon Beach visitors can check into a cottage or condo, wrapped in classic cedar shingles and equipped with a kitchenette and patio, that's operated by hospitality professionals as well as homeowners with space to spare.

Airbnb’s research found visitors book their Cannon Beach getaway at least two months before their trip. Nightly rentals are restricted and people devoted to special events like the crowd-pleasing Sandcastle Contest and hilarious corgi run race to reserve a place.

10 vacation rentals with closeup views of Oregon’s fabulous fall colors

If you live in Oregon, you can look out almost any window and see greenery. Starting now through mid-October, you’ll also see bronze, crimson and golden autumn leaves.

10 Oregon coast getaways to see Shore Acres’ stunning holiday light display: If you’re looking for a place that’s all aglow for the holidays, Shore Acres State Park’s display of 325,000 decorative lights on the southern Oregon coast will blow you away.

Volunteers and park rangers have been hosting Holiday Lights at Shore Acres since 1987.

The free event takes place daily from 4 p.m. to 9:30 p.m. between Thanksgiving and New Year's Eve at the park, which is three miles south of the small fishing town of Charleston and 12 miles southwest of the city of Coos Bay.

Here are 10 vacation stays, from a camper to a midcentury modern house, near the stunning holiday light display, which continues through Dec. 31.

Vacation getaways: Yachts, yurts and other unusual Oregon home rentals: To celebrate a seriously special occasion, you can charter the Disco Volante, a 45-foot yacht with three levels of luxury. We’re talking swim platforms and sun pads, and a ban on red wine and orange Cheetos to protect the pricey teak and tan finishes.

The cost: $999 for two hours then $299 for each additional hour, including the services of a licensed captain.

Or, if you want to pretend to pilot a vessel, there are landlocked pleasure boats on Airbnb or other vacation rental sites.

Vrbo's 2020 Trend Report found a 30% increase in traveler demand for houseboats, yachts, RVs and Airstreams, aka "land yachts," compared to last year.

In this week’s getaway galley, we look at these movable homes plus quirky yurts.

These 5 vacation rentals are hauntingly close to scary movie locations: In the chilling days leading to Halloween, horror movie fans might want to linger on a dead-end street and other places that cinematically spooked them, and then turn their nightmares into dream vacations.

For this week’s vacation getaway roundup, we turned to Portland-based Vacasa to find five places to stay that are hauntingly close to scary film locations, in Oregon and spots for those who may want to creep over state lines.

Where are you heading? What's your favorite home rental?

--Janet Eastman | 503-294-4072

jeastman@oregonian.com | @janeteastman

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