Ashland pickleball Stays, Resort Rentals, & Homes
10.0
Exceptional
(18 Reviews)
1106 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Parking
US $251/Night
For 7 Nights US $1,757
10.0
Exceptional
(1 Review)
1194.79 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $392/Night
For 7 Nights US $2,744
New
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $428/Night
For 7 Nights US $2,998
10.0
Exceptional
(11 Reviews)
1023 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $196/Night
For 7 Nights US $1,372
New
1399.31 ft²
4 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Air Conditioner
US $1,533/Night
For 7 Nights US $10,733
10.0
Exceptional
(10 Reviews)
1098 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $195/Night
For 7 Nights US $1,365
10.0
Exceptional
(8 Reviews)
1399 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $251/Night
For 7 Nights US $1,756
10.0
Exceptional
(6 Reviews)
1800 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $335/Night
For 7 Nights US $2,342
10.0
Exceptional
(3 Reviews)
1550 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $337/Night
For 7 Nights US $2,360
Luxury Places to Stay in Ashland
Over 146+ Luxury Places to Stay in or Near Ashland
10.0
Exceptional
(8 Reviews)
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- Kitchen
US $1,033/Night
For 7 Nights US $7,233
New
1399.31 ft²
6 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $584/Night
For 7 Nights US $4,089
10.0
Exceptional
(2 Reviews)
2600 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $576/Night
For 7 Nights US $4,031
10.0
Exceptional
(3 Reviews)
2260 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $432/Night
For 7 Nights US $3,022
10.0
Exceptional
(23 Reviews)
6 Guests
3 Bedrooms
2 Bathrooms
Condo
- Air Conditioner
- Internet
- Child Friendly
US $404/Night
For 7 Nights US $2,827
New
1797.57 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Parking
- Internet
US $398/Night
For 7 Nights US $2,784
9.8
Exceptional
(20 Reviews)
1300 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Ocean View
- Balcony/Terrace
- View
US $397/Night
For 7 Nights US $2,782
New
2400.35 ft²
16 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
House
- Internet
- Security/Safety
US $368/Night
For 7 Nights US $2,576
10.0
Exceptional
(83 Reviews)
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $355/Night
For 7 Nights US $2,483
Top-Rated Villas with a Pool in Ashland
Over 60+ Top-Rated Private Villas with a Pool in or Near Ashland
10.0
Exceptional
(2 Reviews)
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Kitchen
US $146/Night
For 7 Nights US $1,023
9.6
Exceptional
(45 Reviews)
- Columbia
- Holts Summit
- 3.41 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $175/Night
For 7 Nights US $1,223
9.2
Exceptional
(364 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $170/Night
For 7 Nights US $1,187
9.2
Exceptional
(29 Reviews)
415.75 ft²
4 Bathrooms
Ocean View
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
US $228/Night
For 7 Nights US $1,595
8.8
Fabulous
(1005 Reviews)
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $152/Night
For 7 Nights US $1,064
8.8
Fabulous
(1005 Reviews)
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $115/Night
For 7 Nights US $804
8.6
Fabulous
(1376 Reviews)
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $146/Night
For 7 Nights US $1,020
8.6
Fabulous
(684 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $292/Night
For 7 Nights US $2,044
8.3
Excellent
(145 Reviews)
362.38 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $144/Night
For 7 Nights US $1,009
Pet-Friendly Villas in Ashland
Over 23+ Pet-Friendly Private Villas in or Near Ashland
9.2
Exceptional
(11 Reviews)
250 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $176/Night
For 7 Nights US $1,235
New
2 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $94/Night
For 7 Nights US $658
10.0
Exceptional
(12 Reviews)
1346 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
For 7 Nights US $1,575
8.2
Excellent
(1042 Reviews)
384.42 ft²
7 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Oceanfront
- Hot Tub
US $124/Night
For 7 Nights US $867
10.0
Exceptional
(10 Reviews)
1550 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $287/Night
For 7 Nights US $2,007
9.2
Exceptional
(9 Reviews)
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $341/Night
For 7 Nights US $2,388
10.0
Exceptional
(2 Reviews)
- Columbia
- Holts Summit
- 1.99 mi to center
900 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $154/Night
For 7 Nights US $1,078
9.8
Exceptional
(7 Reviews)
384 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $159/Night
For 7 Nights US $1,110
New
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $96/Night
For 7 Nights US $675
Large Private Villas in Ashland
Over 11+ Large Villas in or Near Ashland for Groups and Families
8.8
Fabulous
(5 Reviews)
1780 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $322/Night
For 7 Nights US $2,255
New
1001.04 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Parking
- Air Conditioner
- Internet
US $309/Night
For 7 Nights US $2,161
New
- Columbia
- Holts Summit
- 2.00 mi to center
1490 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Child Friendly
US $200/Night
For 7 Nights US $1,401
10.0
Exceptional
(1 Review)
- Columbia
- Holts Summit
- 2.00 mi to center
1490 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $222/Night
For 7 Nights US $1,551
9.8
Exceptional
(19 Reviews)
10 Guests
4 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $272/Night
For 7 Nights US $1,904
10.0
Exceptional
(116 Reviews)
- Columbia
- Thornbrook
- 0.43 mi to center
3600 ft²
16 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $789/Night
For 7 Nights US $5,525
9.2
Exceptional
(55 Reviews)
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $219/Night
For 7 Nights US $1,532
5.0
Average
(5 Reviews)
- Columbia
- Thornbrook
- 0.23 mi to center
3000 ft²
9 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $366/Night
For 7 Nights US $2,562
New
13 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $436/Night
For 7 Nights US $3,049
Wheelchair Accessible Holiday Homes in Ashland
Over 47+ Wheelchair Accessible Villas and Holiday Homes in or Near Ashland
10.0
Exceptional
(8 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $144/Night
For 7 Nights US $1,005
8.5
Fabulous
(2 Reviews)
345.98 ft²
7 Bathrooms
Family Friendly
Hotel
- Air Conditioner
- Child Friendly
- Wheelchair Accessible
US $173/Night
For 7 Nights US $1,212
8.4
Excellent
(15 Reviews)
1 Bathroom
Couples Retreat
Hotel
- Fireplace/Heating
- Breakfast
- Parking
US $142/Night
For 7 Nights US $993
10.0
Exceptional
(3 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $269/Night
For 7 Nights US $1,882
8.2
Excellent
(190 Reviews)
645.84 ft²
9 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Spa
US $212/Night
For 7 Nights US $1,482
10.0
Exceptional
(2 Reviews)
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $288/Night
For 7 Nights US $2,016
10.0
Exceptional
(1 Review)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $269/Night
For 7 Nights US $1,882
9.2
Exceptional
(12 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $144/Night
For 7 Nights US $1,005
9.2
Exceptional
(10 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $144/Night
For 7 Nights US $1,005
Ashland Villas, Airbnb and Holiday Homes Under $200
Over 40+ Ashland Private Villas, Airbnb and Holiday Homes Under $200
10.0
Exceptional
(2 Reviews)
728 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
US $188/Night
For 7 Nights US $1,317
New
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- View
- Air Conditioner
US $81/Night
For 7 Nights US $567
New
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $151/Night
For 7 Nights US $1,054
8.0
Excellent
(77 Reviews)
263.72 ft²
2 Bathrooms
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $118/Night
For 7 Nights US $827
New
1400 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $181/Night
For 7 Nights US $1,266
10.0
Exceptional
(47 Reviews)
- Columbia
- Holts Summit
- 2.57 mi to center
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $121/Night
For 7 Nights US $847
10.0
Exceptional
(4 Reviews)
- Columbia
- Holts Summit
- 1.30 mi to center
5 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $183/Night
For 7 Nights US $1,282
9.0
Exceptional
(13 Reviews)
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $197/Night
For 7 Nights US $1,376
10.0
Exceptional
(18 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $124/Night
For 7 Nights US $869
Instantly Bookable Villa Rentals in Ashland
Over 67+ Instantly Bookable Private Villas in or Near Ashland
9.6
Exceptional
(23 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $250/Night
For 7 Nights US $1,747
10.0
Exceptional
(50 Reviews)
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $315/Night
For 7 Nights US $2,206
10.0
Exceptional
(11 Reviews)
1200 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $323/Night
For 7 Nights US $2,263
9.8
Exceptional
(23 Reviews)
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $264/Night
For 7 Nights US $1,846
9.2
Exceptional
(5 Reviews)
1300 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $328/Night
For 7 Nights US $2,299
New
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $259/Night
For 7 Nights US $1,814
10.0
Exceptional
(25 Reviews)
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $245/Night
For 7 Nights US $1,715
10.0
Exceptional
(8 Reviews)
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $220/Night
For 7 Nights US $1,537
New
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $109/Night
For 7 Nights US $766
Book a Last Minute Place to Stay in Ashland
About Ashland Vacation Rentals
Discover over 155 amazing vacation rental options in Ashland with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Ashland.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 486.15 ft², with prices averaging US $292 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Ashland.
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Top Pickleball-Ready Accommodation Types in Ashland
| Type | Count |
|---|---|
| Vacation Homes | 71 |
| Holiday Apartments | 11 |
| Cottages | 8 |
Use these Quick Filters to Find a Vacation Rental in Ashland
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Ashland with PickleTrip™.
Weather in Ashland, MO
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
Top Attractions Around Ashland, MO
PickleTrip offers a large selection of top attractions around Ashland . Research things to do on your vacation before you visit Ashland.
Frequently Asked Questions About Ashland?
What are the top vacation rentals, resorts, and hotels in Ashland with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Ashland. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Ashland!
- South central 4 bedroom house 3 minutes from Faurot Field! Its close and quiet.
- The old rock house!
- Charming 4-Bedroom Home in Jefferson City, MO
- Newly Renovated 3 Bedroom in the Heart of Columbia
- Cedar Lake Condo: Beautiful, completely renovated, 2 Bedroom, 2 Bath Condo
- 3 Bedroom 1 Bath Pet Friendly 5 min to MU
- 1.5 Miles to Mizzou! ~ Spacious & Updated Home~
- Super Close to Mizzou Condo 2 Bed 1 Bath
- Cozy Home Mins to Hospitals*District*Mizzou*Parks
- 2 Bed 1 Bath Southside Columbia 7 min to Mizzou
Which vacation rentals, resorts, or hotels in Ashland is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Ashland? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
- Beautiful, completely renovated, 2 Bedroom, 2 Bath Condo
- Charming 4-Bedroom Home in Jefferson City, MO
- Cozy 3BR Retreat · Quiet Neighborhood · Easy Drive to Mizzou · Fire Pit
How many PickleTrip vacation rentals or resorts are available in Ashland?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 155 properties listed in Ashland in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
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Finding the best prices in Ashland
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