Surf Break Rentals - Vacation Rentals in Skidmore Academy Historic District

Swank House on Main St in Ashland From US $527
         

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10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Barclay Klum House by WanderLodges From US $346
         

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10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
The Ashland Cottage, walk to town From US $256
         

Custom Ashland Home with Fantastic Mountain Views From US $199
         

10.0 (103 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Skidmore Academy Historic District

Over 323+ Luxury Places to Stay in or Near Skidmore Academy Historic District
2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area. From US $995
         

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

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

Top-Rated Vacation Rentals with a Pool in Skidmore Academy Historic District

Over 25+ Top-Rated Vacation Rentals with a Pool in or Near Skidmore Academy Historic District
The Ashland Social | Main House From US $773
         

10.0 (31 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool
The Ashland Social | Guest Studio From US $200
         

10.0 (26 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Arden Forest Inn From US $208
         

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9.8 (104 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Stratford Inn From US $173
         

9.4 (1757 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Lithia Springs Resort From US $187
         

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9.4 (1006 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Palm Cottages From US $213
         

9.2 (214 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Arden Forest Inn From US $180
         

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9.1 (123 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Comfort Inn & Suites Ashland From US $135
         

8.8 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Skidmore Academy Historic District

Over 110+ Pet-Friendly Vacation Rentals in or Near Skidmore Academy Historic District
Bluemoon Vacation Rentals - Bluemoon House From US $505
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
A Cowslip's Belle Inn From US $297
         

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9.6 (43 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Premier Downstairs Flat in Perfect Down Town Location From US $343
         

Courtside Cottage - WalkScore 93 - Dog Friendly From US $339
         

10.0 (62 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxuriously comfortable & peaceful getaway downtown Ashland, with views. From US $231
         

232-Duplex-Private Bathroom-Mountain View From US $432
         

10.0 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Skidmore Academy Historic District

Over 29+ Large Vacation Homes & Villas in or Near Skidmore Academy Historic District
Abigail's Bed and Breakfast Inn From US $235
         

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9.9 (29 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
House + 2 Studios- 3 blocks from the Plaza! From US $626
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Craftsman Style Home in Country Setting From US $309
         

10.0 (164 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Skidmore Academy Historic District

Over 21+ Wheelchair Accessible Vacation Homes in or Near Skidmore Academy Historic District
Ashland Springs Hotel From US $197
         

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9.2 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
BookStayHop - Suite Windsor - Plaza North From US $335
         

5.0 (4 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
BookStayHop - Plaza North Suite Sonoma From US $275
         

5.0 (1 Review)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Child Friendly
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
BookStayHop - Suite Alexander -Downtown with Gorgeous Mountain Views From US $404
         

4.7 (3 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

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

Over 126+ Skidmore Academy Historic District Vacation Rentals and Airbnb Places to Stay Under $200
Pioneer Vacation Rentals - Pioneer South downtown Ashland From US $126
         

The Peerless Hotel by WanderLodges From US $187
         

9.6 (105 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Charming, Comfortable Garden Studio Above The University. From US $74
         

Swank House -Downtown Suite- Pet Friendly From US $196
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Affordable Luxury- One block to Downtown From US $197
         

Private Ashland Townhouse From US $171
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3 From US $68
         

Thistlebee Cottage just outside charming Ashland, Oregon From US $156
         

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

Instantly Bookable Vacation Homes in Skidmore Academy Historic District

Over 140+ Instantly Bookable Vacation Homes in or Near Skidmore Academy Historic District
Luxury condo with king bedroom, two bathrooms, full kitchen. From US $494
         

10.0 (9 Reviews)
Cabin
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
Peaceful 1-bedroom bungalow with AC in charming Ashland From US $245
         

Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen. From US $464
         

Hot tub | Sauna |Firepit |Sleeps 6! From US $744
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Skidmore Academy Historic District Vacation Rentals

With more than 332 Skidmore Academy Historic District vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surfbreakrentals 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 Skidmore Academy Historic District.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Surfbreakrentals Skidmore Academy Historic 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 Skidmore Academy Historic District. Places to stay near Skidmore Academy Historic District are 638.42 ft² on average, with prices averaging US $310 a night.

Surfbreakrentals makes it easy and safe to find and compare vacation rentals in Skidmore Academy Historic 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 Skidmore Academy Historic District

Type Count
Vacation Homes 160
Holiday Apartments 66
Cottages 33
Hotels 31
B&B 18
Cabin Rentals 7
Others 6
Hostels 2
Resorts 2
Villas 1

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

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

Weather in Skidmore Academy Historic District

View the weather forecast for Skidmore Academy Historic District before booking your Skidmore Academy Historic 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

Skidmore Academy Historic District Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 332 in the Skidmore Academy Historic District area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Skidmore Academy Historic District.