Charters By Owner - Vacation Rentals in Ashland

Walk to Mississippi River & Dtwn: Historic Haven! From US $191
         

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10.0 (4 Reviews)
House
  • Parking
  • Security/Safety
  • Fireplace/Heating
Choctaw Hall Bed and Breakfast From US $177
         

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10.0 (382 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Kelly Kottage in Historic Downtown Natchez From US $232
         

9.4 (126 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Above the Law From US $197
         

10.0 (98 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
PIER HAPPINESS on Lake Concordia Lakefront Rental! From US $197
         

The Natchez Gaol, Downtown Natchez From US $195
         

10.0 (53 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Ashland

Over 261+ Luxury Places to Stay in or Near Ashland
Natchez Historic District Home From US $2,448
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Child Friendly
Natchez Historic District Home From US $2,065
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Child Friendly
The River Walk Inn - Rooms 801-806 From US $1,561
         

10.0 (2 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Tons of Fun at 'Camp Flamingo' on Lake Bruin! From US $1,008
         

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New
House
  • Parking
  • Security/Safety
  • Sports/Activities
Darby's Lakehouse Retreat From US $695
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Oxbow Lodge of Lake Bruin From US $689
         

10.0 (65 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Natchez Grand Hotel On The River From US $657
         

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8.4 (2270 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Wheelchair Accessible

Top-Rated Vacation Rentals with a Pool in Ashland

Over 25+ Top-Rated Vacation Rentals with a Pool in or Near Ashland
Stone House Musical B&B From US $164
         

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9.9 (58 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
The Beaumont House From US $175
         

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9.6 (103 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
The Burn Bed and Breakfast From US $167
         

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9.4 (305 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
The Burn Bed and Breakfast From US $168
         

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9.2 (222 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Dunleith Historic Inn From US $162
         

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8.8 (533 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
TownePlace Suites by Marriott Vidalia Riverfront From US $162
         

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8.8 (205 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Natchez Grand Hotel & Suites On the River From US $124
         

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8.6 (1622 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
Hampton Inn & Suites Natchez From US $149
         

8.6 (811 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Ashland

Over 62+ Pet-Friendly Vacation Rentals in or Near Ashland
Charming Lakefront Retreat with Pier and Grill! From US $617
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
610 Franklin | 3/3 | Heart of Downtown From US $556
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic cottage privately situated on the grounds of the Foster Mounds. From US $226
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Darby's Guest House! From US $327
         

9.8 (74 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
610 Franklin: 5B | 1/1 | Heart of Downtown | Washer/Dryer From US $214
         

9.8 (19 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Ashland on PetFriendly.io

Large Vacation Homes & Villas in Ashland

Over 36+ Large Vacation Homes & Villas in or Near Ashland
Ferriday Lakehouse w/Private Dock, Deck, & Yard! From US $479
         

Ferriday Lakehouse w/Private Dock, Deck, & Yard! From US $368
         

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10.0 (2 Reviews)
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Natchez Vacation Rental, Close to Historic Parks! From US $534
         

Downtown Natchez Elegant 1835 Antebellum House From US $602
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Charming Cottage w/Mississippi River Views! From US $257
         

9.8 (43 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Lazy Bear Lodge — The Sandifer’s House on Lake Bruin From US $430
         

10.0 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Ashland

Over 17+ Wheelchair Accessible Vacation Homes in or Near Ashland
The River Walk Inn - Room 802 From US $264
         

10.0 (15 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Devereaux Shields House From US $481
         

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9.0 (121 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
The Bridges Hotel From US $103
         

8.6 (208 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
The River Walk Inn - Room 803 From US $243
         

10.0 (6 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Hampton Inn & Suites Natchez From US $192
         

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8.5 (153 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The River Walk Inn - Room 805 From US $318
         

10.0 (3 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
The River Walk Inn - Room 806 From US $429
         

10.0 (2 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
The River Walk Inn - Room 804 From US $264
         

9.8 (8 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Ashland Vacation Rentals and Airbnb Places to Stay Under $200

Over 95+ Ashland Vacation Rentals and Airbnb Places to Stay Under $200
2feathers inn #1 From US $138
         

9.8 (28 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy Natchez Home - Close to River & Nature From US $112
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
Concord Quarters From US $125
         

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10.0 (114 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
2 Melinda’s Garden Apt From US $137
         

9.8 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The Law Building From US $187
         

9.6 (42 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Ashland

Over 85+ Instantly Bookable Vacation Homes in or Near Ashland
5-Star Spacious & Private Downtown Natchez Home! From US $478
         

The River Walk Inn - Rooms 801-806 From US $1,737
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
1835 Wilkins Townhouse | 3/3 | Walk to Downtown From US $411
         

About Ashland Vacation Rentals

With more than 270 Ashland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chartersbyowner 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 Ashland.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chartersbyowner Ashland, 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 Ashland. Places to stay near Ashland are 599.06 ft² on average, with prices averaging US $306 a night.

Chartersbyowner makes it easy and safe to find and compare vacation rentals in Ashland 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 Ashland

Type Count
Vacation Homes 124
B&B 43
Hotels 35
Holiday Apartments 25
Cottages 21
Cabin Rentals 3
Villas 1

Use these Quick Filters to Find a Vacation Rental in Ashland

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

Weather in Ashland

View the weather forecast for Ashland before booking your Ashland 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

Ashland Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Ashland?
How many vacation rentals are available in Ashland?

Currently, the total number of properties listed in 2026 is over 270 in the Ashland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Ashland.