Maimon Beach - Vacation Rentals in Historic Downtown District

Ashland Lodge w/Lake Views & Game Room Loft From US $454
         

10.0 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Pioneer Vacation Rentals - Pioneer South downtown Ashland From US $126
         

Barclay Klum House by WanderLodges From US $249
         

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10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Custom Ashland Home with Fantastic Mountain Views From US $240
         

10.0 (101 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Chalet #16, Slope Side Ski in Ski Out Spacious Fam From US $910
         

9.2 (7 Reviews)
Ski Chalet
  • Pet Friendly
  • TV
  • Balcony/Terrace
The Red Dragon House From US $208
         

10.0 (106 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Historic Downtown District

Over 338+ Luxury Places to Stay in or Near Historic Downtown District
Luxury Ashland Mountain Escape: Pool, Hot Tub From US $1,083
         

9.6 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area. From US $1,071
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Grandview of Ashland From US $961
         

New
House
  • Air Conditioner
  • Parking
  • View

Top-Rated Vacation Rentals with a Pool in Historic Downtown District

Over 45+ Top-Rated Vacation Rentals with a Pool in or Near Historic Downtown District
The Ashland Social | Main House From US $741
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Ashland Social | Guest Studio From US $203
         

10.0 (25 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Ashland Social | Entire Estate From US $820
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn From US $211
         

10.0 (3 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Lodge Room 7 at Green Springs Inn From US $213
         

10.0 (1 Review)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Arden Forest Inn From US $212
         

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9.8 (103 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Country Willows Inn and Estate From US $186
         

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9.8 (36 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Historic Downtown District

Over 125+ Pet-Friendly Vacation Rentals in or Near Historic Downtown District
The Barn at Emigrant Creek From US $161
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
A Cowslip's Belle Inn From US $223
         

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9.8 (41 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxuriously comfortable & peaceful getaway downtown Ashland, with views. From US $178
         

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything! From US $374
         

Large Vacation Homes & Villas in Historic Downtown District

Over 32+ Large Vacation Homes & Villas in or Near Historic Downtown District
Bluemoon Vacation Rentals - Bluemoon House From US $505
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Homey Rustic Cabin in the Cascades From US $218
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
House + 2 Studios- 3 blocks from the Plaza! From US $595
         

9.8 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous Lakeside BarnHOUSE + SAUNA! From US $324
         

9.2 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Historic Downtown District

Over 24+ Wheelchair Accessible Vacation Homes in or Near Historic Downtown District
Spotless, Cozy, Dog Friendly, Family Home From US $211
         

4.9 (10 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Arden Forest Inn From US $180
         

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9.1 (123 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Callahan's Mountain Lodge From US $115
         

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8.8 (1177 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Cozy Cabin with great views in a mountain valley by a lake. From US $145
         

New
Cabin
  • Air Conditioner
  • Wheelchair Accessible
  • Bedding/Linens
Lithia Springs Resort From US $199
         

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8.8 (553 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Ashland Springs Hotel From US $134
         

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9.2 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Vineyard Home w/ 360 Views, private walking, pet-friendly, 2 miles from town! From US $648
         

4.7 (39 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Bayberry Inn B&B and Oregon Wellness Retreat From US $276
         

10.0 (15 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Historic Downtown District Vacation Rentals and Airbnb Places to Stay Under $200

Over 138+ Historic Downtown District Vacation Rentals and Airbnb Places to Stay Under $200
Owl Creek Cabin Mountain Getaway near Ashland, Oregon From US $174
         

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10.0 (1 Review)
House
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
Lithia Springs Resort From US $126
         

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9.4 (1003 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44 From US $197
         

10.0 (4 Reviews)
Cabin
  • Parking
  • TV
  • Security/Safety
Private Ashland Townhouse From US $197
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cabin #4 at Hyatt Lake Resort From US $179
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • TV
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3 From US $78
         

Instantly Bookable Vacation Homes in Historic Downtown District

Over 177+ Instantly Bookable Vacation Homes in or Near Historic Downtown District
Monthly Single family house just blocks to Ashland's downtown From US $152
         

New
House
  • Security/Safety
  • Bedding/Linens
  • Fireplace/Heating
Charming well appointed Cottage in Ashland (800 + sq. ft.) From US $219
         

10.0 (18 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Luxury condo with king bedroom, two bathrooms, full kitchen. From US $494
         

10.0 (9 Reviews)
Cabin
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen. From US $582
         

Hot tub | Sauna |Firepit |Sleeps 6! From US $546
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Historic Downtown District Vacation Rentals

With more than 347 Historic Downtown District vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Maimonbeach and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Historic Downtown District.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Maimonbeach Historic Downtown District, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Historic Downtown District. Places to stay near Historic Downtown District are 619.06 ft² on average, with prices averaging $276 a night.

Maimonbeach makes it easy and safe to find and compare vacation rentals in Historic Downtown District with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Historic Downtown District

Type Count
Vacation Homes 135
Cabin Rentals 60
Hotels with Suites 52
Holiday Apartments 51
Cottages 18
Others 11
B&B 9
Resorts 4
Villas 3
Hostels 2
Ski Chalet Rentals 2

Use these Quick Filters to Find a Vacation Rental in Historic Downtown District

Pro Tip: Maimonbeach makes it easy to compare the best listings on Maimonbeach homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Maimonbeach homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Historic Downtown District.

Weather in Historic Downtown District

View the weather forecast for Historic Downtown District before booking your Historic Downtown District Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Historic Downtown District Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Historic Downtown District?
How many vacation rentals are available in Historic Downtown District?

Currently, the total number of properties listed in 2026 is over 347 in the Historic Downtown District area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Historic Downtown District.