
Holiday rentals with breakfast in Ashland
Find and book unique rentals with breakfast on Airbnb
Quick stats about holiday rentals with breakfast included in Ashland

Total holiday rentals
Explore 10 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at $207 SGD per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Ashland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ashland rentals

4.9 Average rating
Ashland stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with breakfast in Ashland
Guests agree: these breakfast rentals are highly rated for location, cleanliness and more.

Cozy European Cottage 2 bd + 1 bath
Discover the charm of Ashland from this beautiful 2-bedroom, 1-bath Additional Dwelling Unit—a private haven with its own entrance and no shared walls. It's insulated from the main house by their garage and laundry room. It features an outdoor patio, central heat and air, and a fully stocked kitchen with a sink, dishwasher, full-size fridge/freezer, microwave, portable oven, and 2 electric burners. Nestled in a quiet neighborhood, this 875 sqft space offers comfort, convenience, and local flair.

Orchard Home Cottage *Private• Cozy• Peaceful*
*NO PETS* Enjoy Southern Oregon by staying in our peaceful bright cottage. Perfect for those who want a quiet getaway close to all the Rogue Valley has to offer. It is situated toward the rear of our property w/private parking and its own fenced patio. We are located 4 miles from Jacksonville where you can hear the sounds of the Britt Festival. Ashland, home of Oregon's Shakespeare Festival is 20 minutes away. Lakes, hiking trails, and rivers are all around for those looking for adventure.

Lily Pad/#1 Best Location/Full Kitchen/Luxurious
The Lily Pad is an elegantly appointed 1 bedroom home with a fully stocked kitchen with counter top dining, perfect for preparing a gourmet meal after a visit to the local farmers market. The private master bedroom has high quality, comfortable linen and a private patio. There is a gorgeous master bathroom and inviting living room made for relaxation. Concierge service available. *If you need more space both the Lily Pad and The Tigers Den can be booked together to sleep a total of 6 people.

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.

Magnolia Suite
Delightful ground level apartment of my private home. Separate entrance with outside patio off of lush back yard. Self contained apartment with bedroom, (Queen Sized Bed). Private bathroom with walk-in shower. Full kitchen with refrigerator, range, microwave and dishwasher. Dining area at kitchen island, off of living room. Electric fireplace. Off street parking in driveway. Close to airport and shopping. Quiet neighborhood. It is like staying with family without the pesky relatives.

Perfect Location! Entire house, pet friendly!
Looking for a place for an extended stay on a business trip to Grants Pass? Message me! Awesome neighborhood! Quiet & close to the Historical District which has wonderful restaurants and shopping. Good location for all activities in the area. Lots of natural light. Fenced back yard for your four legged friends. The front deck has table and chairs so you can sit out and enjoy morning coffee or evening glass of wine! The prefect location to base your Southern Oregon adventure from!

Cool Blue Waters-Guest Suite
Enjoy our newly renovated guest suite, perfect for short stays of 26 nights max. Cool Blue Waters is perfect for traveling professionals, families and dog lovers. We are centrally located in the heart of historic Grants Pass. The guest suite is attached to your Host's home and includes: Queen bed, office area, Wi-fi, TV, futon couch/folding bed, walk-in closet, kitchenette with coffee and breakfast items, Private Bathroom, toiletries, Pool and Private patio area.

Circle G Bunkhouse on the Salant Family Ranch WIFI
NEW ! we have Wifi Wide open pastures located in the Little Applegate Valley along the river and in the forest. Historic Salant Family Ranch is a year round working cattle operation. Experience sunrises and sunsets over lush green pastures full of grazing cattle in all 4 seasons. Go back 100 years ago when raising beef was a well respected and profitable trade. Still is with this ranch today. We raise BEEF ! We sell BEEF! We love cows.............

Two room private suite on river, friendly hosts.
Our place has just been remodeled. It is close to public transport, the city center, and family-friendly activities. We are within walking distance of a store, and a great restaurant. You’ll love our place because of the outdoor spaces, the light, and sitting next to the Rogue River watching the rafters, boats, geese, Egrets, Herons, and eagles.. Our place is good for couples, solo adventurers, business travelers, and families (with kids).

Family-Friendly 2-BR Apartment
Enjoy a relaxing, family-friendly stay in our spacious 3-bedroom House/ Apartment just a few minutes from the airport. Ideal for family gatherings, temporary stays during home renovations, or company events, this suite offers comfortable bedrooms with ample space to unwind. With easy access to downtown Medford, local dining, and attractions, plus on-site parking and Wi-Fi, it’s the perfect home-away-from-home for your group’s needs.

Sunset View Yurt of Applegate Valley with HOT TUB!
NO CLEANING FEE! Large 24 ft yurt located on our 5 acre property. Gorgeous views to the west. Includes a king size bed, and queen sofa bed. Located in Applegate Valley. Many fabulous wineries nearby. We're 6 miles south of downtown Grants Pass, and 2 miles north of Murphy. Enjoy the hot tub under the stars, or catch a spectacular sunset. It's all good! Please note: Well behaved children are welcome.

Jacksonville Jewel
Snuggle into this comfy n spacious condo just 2 blocks from Historic J'ville and the Britt Music & Arts Festival. Grocery store is next door when you decide to cook in the fully stocked kitchen with all the amenities you need. Guest parking lot or on the street and plenty of hiking trails to explore
Popular amenities for rentals with breakfast in Ashland
House rentals with breakfast

Private Pulchritudinous 1918 Suite

Comfy Medford ranch with a Red door

The Homestead

Peaceful Place, Beautiful Space

Cowgirl Craftsman - Private King Suite Upstairs

Home on The Rogue: Steelhead Ally

Close to Rogue Rvr, 5 minutes to Historical Dist.

safe area, king bed,smart tv, 1.5 bath, love pets
Other holiday rentals with breakfast

Heart & Haven Suite- 2 Beds & Private Entrance

Premium King Room W/Private Bath

Chanticleer Inn: Maitre, garden-view room

Jacksonville Inn | RM #7 | Queen Guest Room

3 Family-friendly Units! Near GP Shopping Center!

King Suite at Callahan's Mountain Lodge

The Inn at Hummingbird Estate - Japanese Maple

ADA King w/ Roll-In Shower & Breakfast | Near MFR
When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $206 SGD | $200 SGD | $233 SGD | $297 SGD | $300 SGD | $299 SGD | $297 SGD | $288 SGD | $244 SGD | $247 SGD | $224 SGD | $226 SGD |
| 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 |
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