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Check prices for these dates, December 13 – 14, 2026
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.
Nestled between mountains and Little Squam Lake, this relaxing town invites visitors to explore the charming Pauline E Glidden Toy Museum and historic Whipple House. Hike the scenic Whitten Woods Trailhead in the morning, then spend afternoons discovering local heritage at the Railroad Station Museum where train history comes alive.
Glynn House Inn is a fantastic choice for travelers seeking a blend of comfort and adventure in Ashland, boasting an impressive 9.6 rating. Nestled in a charming Victorian property, this inn is superb for those who appreciate attentive service and a cozy atmosphere. Guests rave about the delicious breakfast and the inn's prime location, which offers easy access to nearby ski rentals and cross-country skiing, making it an ideal retreat for winter sports enthusiasts.
For those who love the outdoors, Cheney House B&B is another delightful option, rated 9.4. Its stunning mountain views and proximity to hiking and biking trails make it a popular pick for adventurous couples or solo travelers looking to explore the natural beauty of the area. The historical charm of this Victorian property, combined with the owner’s warm hospitality and homemade breakfast, ensures a memorable stay filled with comfort and relaxation.
Prices for B&Bs in Ashland often vary, but you can find a great deal from $64 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Ashland B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
In Ashland, the Glynn House Inn stands out as a family-friendly retreat. This welcoming property offers complimentary rollaway beds and cribs, making it easy for families to accommodate children comfortably. With daily housekeeping and a lovely garden for kids to explore, parents can relax knowing there’s plenty of space for play. The inn also features a kitchen, allowing families to prepare snacks or meals at their convenience, adding a layer of comfort to your stay.
Another delightful option is the Cheney House B&B, which provides a fun arcade game room that will surely entertain kids of all ages. This charming property also includes daily housekeeping and a beautiful garden, superb for family picnics or leisurely strolls. With a focus on creating a friendly setting, both of these B&Bs ensure that families can enjoy quality time together while feeling at home.
Glynn House Inn in Ashland is a pet-friendly haven for travelers seeking a cozy getaway. This charming Victorian property accommodates service animals and features an array of thoughtful amenities that ensure a comfortable stay. Guests can enjoy the warmth of a fireplace, unwind on the patio or balcony, and indulge in premium bedding, ensuring restful nights after a day of adventure.
For those with a taste for the outdoors, Glynn House Inn is ideally situated near ski rentals and lessons, great for families looking to hit the slopes together. The nearby beaches also offer family-friendly activities, making this inn a versatile choice for both relaxation and adventure.
The best time to book a B&B in Ashland is during the enchanting spring months from March to May, when the town comes alive with blooming flowers and vibrant arts events. This season not only offers mild temperatures, generally ranging from the low 40s to mid-70s Fahrenheit, but also provides a fantastic opportunity to explore the famous Oregon Shakespeare Festival, which runs from February through October and peaks in the summer.
In particular, April is a delightful month to visit Ashland, as the weather is pleasantly warm and the crowds haven't yet reached their summer highs. This makes it an ideal time for outdoor activities, such as hiking in the nearby Lithia Park or enjoying a leisurely stroll through the charming downtown area filled with unique shops and local eateries.
For those seeking a more budget-friendly experience, consider planning your trip in November. While this month may see fewer tourists, it still offers a cozy atmosphere superb for enjoying the town's cultural offerings and beautiful fall scenery.
Every Ashland B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Ashland B&Bs.