Find Hotels with Connecting Rooms in Ashland, OR

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Check availability on Ashland Hotels with Connecting Rooms

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Top Ashland Hotels with Connecting Rooms

Exterior
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

2.5 star property
Ashland
9.2 out of 10, Wonderful, (1013)
"Clean and friendly staff"
United States
Liza Rene
$99 nightly
The price is $111
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express & Suites Ashland by IHG
Lobby sitting area
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3.0 star property
Ashland
9.0 out of 10, Wonderful, (1520)
"I love staying here because the decoration is so great and the food and service is phenomenal."
United States
Roxane
$92 nightly
The price is $103
Jan 2 - Jan 3, 2026
Total with taxes and fees
Ashland Hills Hotel & Suites
Free daily on-the-go breakfast
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 star property
Ashland
8.8 out of 10, Excellent, (1186)
"The room was clean and the staff was very friendly. Would definitely stay again."
Canada
Susan
$70 nightly
The price is $79
Dec 9 - Dec 10
Total with taxes and fees
Flagship Inn of Ashland
Lobby
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 star property
Historic Downtown District
8.6 out of 10, Excellent, (1008)
"The Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel"
United States
Suzanne
$105 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
The Bard's Inn, BW Signature Collection by Best Western
Exterior
Best Western Windsor Inn

Best Western Windsor Inn

2.5 star property
Ashland
9.0 out of 10, Wonderful, (1011)
"Location was convenient for traveling thru Ashland, but not so convenient if you wish to attend the Festival as you have to drive into town. "
United States
Janet
$109 nightly
The price is $122
Dec 7 - Dec 8
Total with taxes and fees
Best Western Windsor Inn
Exterior
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 star property
Ashland
8.6 out of 10, Excellent, (1027)
"Clean, great pool, super friendly staff. "
United States
Scott
$84 nightly
The price is $85
Jan 2 - Jan 3, 2026
Total with taxes and fees
Comfort Inn & Suites Ashland
Outdoor dining
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3.0 star property
Ashland
8.8 out of 10, Excellent, (1010)
"I stayed at this property several times, it looked to be very empty and check in. It was late after 4 PM. checking people seem to be disinterested in finding out what the issue was rectifying the problem or even really caring, they blame this on off-season and just seem to be very nonchalant about it."
United States
Rebecca
$119 nightly
The price is $133
Dec 3 - Dec 4
Total with taxes and fees
Plaza Inn & Suites at Ashland Creek
Room, 2 Queen Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, free WiFi
Scottish Inn

Scottish Inn

2.5 star property
Ashland
7.8 out of 10, Good, (666)
"Easy parking. Convenient to downtown and shopping"
United States
Michael
$69 nightly
The price is $77
Dec 7 - Dec 8
Total with taxes and fees
Scottish Inn
Standard Room, 2 Queen Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, free WiFi
Cedarwood Inn of Ashland

Cedarwood Inn of Ashland

2.0 star property
Ashland
7.4 out of 10, Good, (1002)
"We’ve stayed here twice. Nice place for reasonable price."
United States
Mai
$95 nightly
The price is $106
Dec 9 - Dec 10
Total with taxes and fees
Cedarwood Inn of Ashland
Main House | Terrace/patio
A Cowslip's Belle Inn

A Cowslip's Belle Inn

3.0 star property
Ashland
9.8 out of 10, Exceptional, (40)
"Lovely yard courtyard area with koi pond"
United States
Paul
$200 nightly
The price is $223
Dec 3 - Dec 4
Total with taxes and fees
A Cowslip's Belle Inn
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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Find out more about Ashland

Discover top Ashland attractions

In Ashland, Oregon, families and adventure-seekers alike will find a delightful array of experiences waiting for them. Start your journey at the Oregon Shakespeare Festival, where world-class performances captivate audiences in an enchanting outdoor setting, making it a perfect outing for theater lovers of all ages. After the show, explore Lithia Park, known for its picturesque landscapes, serene duck ponds, and a variety of trails that cater to both leisurely strolls and invigorating hikes. For those seeking a taste of local culture, the Ashland Artisan Market showcases an array of handcrafted goods, from unique jewelry to delicious local produce, perfect for a family outing or a chance to find that special souvenir. Adventure enthusiasts can also take a short drive to Mount Ashland for breathtaking views and thrilling outdoor activities like skiing in winter or mountain biking in summer. When it comes to accommodation, consider staying in the charming downtown area, where boutique hotels offer personalized service and easy access to all these attractions. After a day of exploration, retreat to your hotel, unwind in their cozy lounges, and savor locally sourced breakfasts that will energize you for the adventures ahead. Ashland is a place where quality and convenience come together, ensuring a memorable experience for the whole family.

Find the best hotels with connecting rooms in Ashland

For travelers seeking accommodations in Ashland, Oregon with connecting room options, these top hotels provide convenience and comfort for groups or families. Each hotel is equipped to ensure a seamless stay for guests needing extra space.

Holiday Inn Express & Suites Ashland by IHG

  • Why it's great for extra space: The Holiday Inn Express & Suites is a great fit for those requiring connecting rooms, with an impressive guest review rating of 9.2. This hotel offers comfortable, well-equipped rooms with connecting options, making it a convenient choice for families. Guests will appreciate the indoor pool and hot tub, perfect for relaxation.
  • Other amenities: In addition to connecting rooms, the hotel features 24-hour fitness facilities and free breakfast to fuel your day. Guests can enjoy self-parking, complimentary Wi-Fi, and a microwave for added convenience. The hotel also offers accessible features, ensuring a comfortable stay for all guests.
  • Nearby attractions: Southern Oregon University - 1.37 miles, Schneider Museum of Art - 1.75 miles, ScienceWorks Hands-On Museum - 2.07 miles

Stratford Inn

  • Why it's great for extra space: The Stratford Inn is an excellent choice for those needing connecting rooms, with a high guest review rating of 9.2. The hotel offers spacious rooms featuring connecting rooms, making it perfect for groups or families wanting to stay close together while enjoying their own private spaces. Guests will appreciate the indoor pool and hot tub, ideal for relaxation after a day of exploring Ashland.
  • Other amenities: In addition to connecting rooms, the Stratford Inn features a kitchenette in each room, allowing for convenient meal preparation. Travelers can enjoy a complimentary breakfast, a terrace for fresh air, and daily housekeeping services. Nearby activities such as winery tours and snow tubing add to the appeal, while additional features like air conditioning, a game room, and a concierge service enhance the overall experience.
  • Neighborhood: Siskiyou-Hargadine Historic District
  • Nearby attractions: Southern Oregon University - 0.54 miles, Oregon Cabaret Theatre - 0.49 miles, Ashland Library - 0.33 miles

Flagship Inn of Ashland

  • Why it's great for extra space: The Flagship Inn is a fantastic pick for travelers seeking connecting rooms, a solid guest review rating of 9.0. This budget-friendly hotel offers comfortable accommodations with connecting room options, making it ideal for groups. Guests will enjoy the outdoor pool and complimentary breakfast to start their day off right.
  • Other amenities: Beyond connecting rooms, the Flagship Inn provides free Wi-Fi and air conditioning for added comfort. The hotel features a garden area for guests to relax in and a kitchen in select rooms for convenience. Self-parking is free, and nearby activities include mountain biking and hiking, ensuring guests have plenty of options to explore Ashland.
  • Nearby attractions: Southern Oregon University - 0.2 miles, Schneider Museum of Art - 0.43 miles, ScienceWorks Hands-On Museum - 0.96 miles

Ashland Hills Hotel & Suites

  • Why it's great for extra space: Ashland Hills Hotel & Suites caters perfectly to travelers needing connecting rooms, with an excellent guest review rating of 8.8. This hotel offers spacious suites with connecting options, making it great for families or groups. Guests can unwind at the outdoor pool or indulge in the hot tub after a day of adventures.
  • Other amenities: Additional features include an onsite spa offering body treatments, a terrace to enjoy fresh air, and air conditioning for a comfortable stay. Guests can take advantage of complimentary self-parking, a fitness center, and nearby skiing options that enhance the experience. The hotel also provides bicycles for onsite use, making it easy to explore the surrounding area.
  • Nearby attractions: Southern Oregon University - 1.28 miles, Schneider Museum of Art - 1.65 miles, ScienceWorks Hands-On Museum - 1.98 miles

Plaza Inn & Suites at Ashland Creek

  • Why it's great for extra space: The Plaza Inn & Suites at Ashland Creek is ideal for travelers in need of connecting rooms, with a solid guest review rating of 8.6. This hotel provides connecting room options, offering flexibility for larger groups or families. Guests can relax in the hot tub or enjoy the outdoor space for a refreshing getaway.
  • Other amenities: The hotel features a garden area, fitness center, and complimentary breakfast to start the day. Additional amenities include self-parking options, electric car charging stations, and daily housekeeping services. Nearby attractions such as wineries and skiing areas add to the hotel's appeal, making it a convenient base for exploring Ashland.
  • Nearby attractions: Lithia Park - 0.27 miles, Allen Elizabethan Theatre - 0.32 miles, Angus Bowmer Theatre - 0.32 miles

Top Ashland Hotel Reviews

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"I love staying here because the decoration is so great and the food and service is phenomenal."
Roxane 1-night trip
Posted 1 day ago
Ashland Hills Hotel & Suites

Frequently asked questions

How much do hotels with connecting rooms in Ashland cost?
You can expect to pay somewhere from $77 to $223 per night for hotels with connecting rooms in Ashland. Whatever your budget, the perfect stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with connecting rooms in Ashland?
There are multiple hotels with connecting rooms in Ashland with a total average guest review rating of 8.6. Ashland Hills Hotel & Suites comes highly recommended if you're traveling with the kids or you simply want to spread out. This 3-star hotel also offers pool sun loungers and a terrace. Best Western Windsor Inn is another top option with connecting rooms. It has a 2.5-star rating and conveniences such as mountain views and an electric car charging station.
How many hotels with adjoining rooms are there in Ashland?
Take your pick of 11 hotels with adjoining rooms in Ashland. No matter if you're traveling with the kids or organizing a weekend escape with some friends, Expedia will help you find the best space for your crew.
What are the best cheap hotels with connecting rooms in Ashland?
With hotels with connecting rooms starting from $77 per night, it may be tempting to extend your stay in Ashland! One property that's easy on your finances is Best Western Windsor Inn. It comes with the layout you need as well as a garden and an electric car charging station. Another cost-effective choice is Holiday Inn Express & Suites Ashland, an IHG Hotel. Besides connecting rooms, it offers a swimming pool and free internet services. Visiting free attractions in Ashland will stretch your travel budget even further. Allen Elizabethan Theatre and Thomas Theatre are on the itineraries of many tourists. With the cash you save, you can explore some more! This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels with connecting rooms in Ashland?
Settle in at Ashland Hills Hotel & Suites, a 3-star option just a short drive from downtown. Amenities here include complimentary breakfast and a playground. Another family-friendly hotel with connecting rooms is Best Western Windsor Inn. Complimentary breakfast and laundry facilities help make this 2.5-star stay a hit with guests. Once you've checked in, there are plenty of family-friendly attractions to explore in and around Ashland. ScienceWorks Hands-On Museum and Mount Ashland Ski Area promise fun for all ages.
Why book your hotel with connecting rooms in Ashland with Expedia?
Expedia makes it a breeze to find your ideal hotel with connecting rooms in Ashland. Traveling with the family? Use our filters to search for properties with a kitchen or a pool. If you have a certain budget, click on how much you want to spend and the preferred star rating of your hotel. We'll help you find the right fit whatever your plans or style of travel.
How can I find cheap hotels with connecting rooms in Ashland?
A good way to compare cheap hotels with connecting rooms in Ashland is with Expedia's nifty filter tool. Tailor your search results by amenities, budget and star rating to snag unbeatable rates in a couple of clicks.
What is there to do in Ashland near my hotel with connecting rooms?
Ashland has enough sights and activities to keep you on the hop for weeks (or months!), beginning with Oregon Shakespeare Festival. Mount Ashland Ski Area, Allen Elizabethan Theatre and Oregon Cabaret Theatre are other wonderful attractions. If you're in town a while, Thomas Theatre and Angus Bowmer Theatre are nice final touches to your itinerary.

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