Holiday In The Hamptons - Vacation Rentals in Historic Downtown District

Ashland Lodge w/Lake Views & Game Room Loft From US $549
         

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

The Mountain Ave House by WanderLodges From US $424
         

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10.0 (7 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Custom Ashland Home with Fantastic Mountain Views From US $217
         

10.0 (99 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Red Dragon House From US $160
         

10.0 (103 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Historic Downtown District

Over 332+ Luxury Places to Stay in or Near Historic Downtown District
Luxury Ashland Mountain Escape: Pool, Hot Tub From US $1,079
         

9.4 (3 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
Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room. From US $779
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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

Over 46+ Top-Rated Vacation Rentals with a Pool in or Near Historic Downtown District
Indulgent Retreat: 3 King Suites, Pool & Hot Tub From US $360
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Ashland Studio: King Bed, 1 mile from Plaza! From US $204
         

10.0 (25 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn From US $214
         

10.0 (3 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Lodge Room 7 at Green Springs Inn From US $214
         

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 (33 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Ashland Luxury: 4 King suites, pool & hot tub From US $694
         

9.8 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Historic Downtown District

Over 124+ 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 (40 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Courtside Cottage - WalkScore 93 - Dog Friendly From US $213
         

10.0 (59 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Hyatt Prairie Mountain Cabin From US $412
         

10.0 (57 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Historic Downtown District

Over 33+ Large Vacation Homes & Villas in or Near Historic Downtown District
Homey Rustic Cabin in the Cascades From US $352
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Bluemoon Vacation Rentals - Bluemoon House From US $505
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
House + 2 Studios- 3 blocks from the Plaza! From US $568
         

9.6 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous Lakeside HOUSE + Indoor SAUNA! From US $357
         

8.8 (5 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
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 $146
         

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8.8 (1174 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Spotless, Cozy, Dog Friendly, Family Home From US $211
         

4.9 (10 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Lithia Springs Resort From US $199
         

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8.9 (630 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express & Suites Ashland by IHG From US $95
         

9.2 (1012 Reviews)
Hotel
  • 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
Bayberry Inn B&B and Oregon Wellness Retreat From US $294
         

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

Historic Downtown District Varoom and Airbnb Places to Stay Under $200

Over 148+ Historic Downtown District Varoom 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 $156
         

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9.4 (1002 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Charming well appointed Cottage in Ashland (800 + sq. ft.) From US $103
         

Hyatt Lake Mountain Retreat From US $195
         

9.8 (86 Reviews)
Cabin
  • Parking
  • Pet Friendly
  • TV
Thistlebee Cottage just outside charming Ashland, Oregon From US $136
         

9.6 (4 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Historic Downtown District

Over 168+ 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
Luxury condo with king bedroom, two bathrooms, full kitchen. From US $511
         

10.0 (9 Reviews)
Cabin
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
Luxury condo with king bedroom, two bathrooms, full kitchen. From US $494
         

10.0 (9 Reviews)
Cabin
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything! From US $374
         

Soda Mountain Cabin w/Jacuzzi and Wood Stove at Green Springs Inn From US $391
         

Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44 From US $300
         

10.0 (4 Reviews)
Cabin
  • Parking
  • TV
  • Security/Safety

About Historic Downtown District Vacation Rentals

With more than 341 Historic Downtown District vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidayinthehamptons 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 Holidayinthehamptons 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 630.14 ft² on average, with prices averaging $261 a night.

Holidayinthehamptons 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 129
Cabin Rentals 57
Holiday Apartments 55
Hotels with Suites 51
Cottages 19
Others 11
B&B 8
Resorts 4
Villas 3
Hostels 2
Ski Chalet Rentals 1

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

Pro Tip: Holidayinthehamptons makes it easy to compare the best listings on Holidayinthehamptons homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidayinthehamptons 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