Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Oakland vacation rentals

House (2 Bedrooms) | Interior
Walk to Wku, Bars & Dining! Updated Duplex Home

Cottage in Bowling Green

Walk to Wku, Bars & Dining! Updated Duplex Home
3.0 star property
10.0 out of 10, Exceptional, (1)
"Super location, super clean, good information before arrival, newly renovated and would definitely stay there again"
Denmark
Jakob
The price is ￥16,197
￥40,517 total
includes taxes & fees
Dec 18 - Dec 19
Walk to Wku, Bars & Dining! Updated Duplex Home
Exterior
Cozy Tiny Home at Traveler's Cellar Winery in Rockfield with Vineyard views.

Cabin in Rockfield

Cozy Tiny Home at Traveler's Cellar Winery in Rockfield with Vineyard views.
10.0 out of 10, Exceptional, (14)
"Lovely place!"
United States
R
The price is ￥14,114
￥29,108 total
includes taxes & fees
Dec 12 - Dec 13
Cozy Tiny Home at Traveler's Cellar Winery in Rockfield with Vineyard views.
Exterior
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.

Vacation Home in Cave City

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
9.0 out of 10, Wonderful, (29)
"It was a great place for a quick stay. "
United States
Sarah B.
The price is ￥11,213
￥30,162 total
includes taxes & fees
Dec 14 - Dec 15
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Smart TV, fireplace, books
Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola. Serene.

Cottage in Cub Run

Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola. Serene.
9.4 out of 10, Exceptional, (57)
"Wonderful stay"
United States
Magdalena F.
The price is ￥13,705
￥33,137 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola. Serene.
Property grounds
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave

Cabin in Mammoth Cave

Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave
9.6 out of 10, Exceptional, (22)
"We absolutely loved our stay. It was quiet and beautiful!"
United States
Elana T.
The price is ￥14,795
￥33,136 total
includes taxes & fees
Dec 12 - Dec 13
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave
Fridge, microwave, oven, stovetop
Charming 3-bedroom house "Cavern" with tons of amenities in Cave City.

Vacation Home in Cave City

Charming 3-bedroom house "Cavern" with tons of amenities in Cave City.
9.6 out of 10, Exceptional, (16)
"This was a perfect house for our family to stay in. Clean and well kept. We would definitely stay here again. "
United States
Anonymous traveler
The price is ￥15,418
￥39,347 total
includes taxes & fees
Dec 12 - Dec 13
Charming 3-bedroom house "Cavern" with tons of amenities in Cave City.
Exterior
A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park

Cottage in Park City

A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park
10.0 out of 10, Exceptional, (12)
"Darling clean cabin centrally located. Would definitely stay again!"
United States
K G.
The price is ￥31,148
￥53,223 total
includes taxes & fees
Dec 12 - Dec 13
A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park
Fridge, microwave, oven, stovetop
Hot Tub and Fire Pit near Mammoth Cave National Park- Pet Friendly

Vacation Home in Cave City

Hot Tub and Fire Pit near Mammoth Cave National Park- Pet Friendly
9.6 out of 10, Exceptional, (9)
"We stayed in this lovely rental so we could visit Mammoth Cave National Park. The home was clean and welcoming: the host even supplied dog treats and bowls for our dogs. We very much enjoyed the space and we had everything that we needed to be comfortable for our long weekend stay!"
United States
Kristi J.
The price is ￥17,910
￥47,321 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hot Tub and Fire Pit near Mammoth Cave National Park- Pet Friendly
Exterior
The Maple Retreat at Park Mammoth

Cabin in Park City

The Maple Retreat at Park Mammoth
3.0 star property
9.8 out of 10, Exceptional, (13)
"Wonderful property and ambiance. "
United States
neil
The price is ￥22,344
￥38,410 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Maple Retreat at Park Mammoth
Fridge, microwave, oven, stovetop
Peaceful private 3 BR new home near Mammoth Cave.

Vacation Home in Cave City

Peaceful private 3 BR new home near Mammoth Cave.
9.8 out of 10, Exceptional, (37)
"Great place to stay after touring the caves. "
United States
Matt D.
The price is ￥12,475
￥21,478 total
includes taxes & fees
Dec 23 - Dec 24
Peaceful private 3 BR new home near Mammoth Cave.
House (2 Bedrooms) | Interior
6 Mi to Mammoth Cave! Mtn-view Home w/ Fire Pit

Cottage in Cave City

6 Mi to Mammoth Cave! Mtn-view Home w/ Fire Pit
2.0 star property
The price is ￥14,484
￥43,797 total
includes taxes & fees
Dec 14 - Dec 15
6 Mi to Mammoth Cave! Mtn-view Home w/ Fire Pit
Property grounds
Cozy House with lots of charm!

Cottage in Bowling Green

Cozy House with lots of charm!
10.0 out of 10, Exceptional, (36)
"Enjoyed the trip to NCM. "
United States
Steven J.
The price is ￥24,140
￥44,209 total
includes taxes & fees
Dec 12 - Dec 13
Cozy House with lots of charm!
Fridge, microwave, oven, stovetop
Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!

Vacation Home in Cave City

Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!
10.0 out of 10, Exceptional, (37)
"Great stay & good location to many activities & Mammouth cave. Although wasn't able to find any utensils for the grill. "
United States
RONDA N.
The price is ￥23,672
￥44,895 total
includes taxes & fees
Dec 12 - Dec 13
Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!
Exterior
Exile on Main Street

Cottage in Brownsville

Exile on Main Street
10.0 out of 10, Exceptional, (58)
"Nice stay! As described. "
United States
Brad T.
The price is ￥22,582
￥43,911 total
includes taxes & fees
Dec 15 - Dec 16
Exile on Main Street
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Quiet Apartment

Vacation Home in Brownsville

Quiet Apartment
9.8 out of 10, Exceptional, (36)
"My husband and I stayed here one night while visiting Mammoth Cave and it perfectly suited our needs. The property was quiet, the bed was comfortable and it was reasonably close to Mammoth Cave National Park. We would stay here again if we ever return to the area."
United States
Caitlin W.
The price is ￥15,418
￥29,016 total
includes taxes & fees
Dec 17 - Dec 18
Quiet Apartment
Fridge, microwave, oven, stovetop
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave

Vacation Home in Brownsville

The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
10.0 out of 10, Exceptional, (7)
"The property was beautiful and clean and had thoughtful additions like a high chair, play pin, basket ball for playing outside, and plenty of svds books and board games. Great place to stay and very close to mammoth cave visitor center."
United States
Chasidy P.
The price is ￥23,005
￥53,194 total
includes taxes & fees
Dec 12 - Dec 13
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
Smart TV
Hunts Bend Private Getaway!

Vacation Home in Bowling Green

Hunts Bend Private Getaway!
10.0 out of 10, Exceptional, (8)
"A wonderful property in a great location!"
United States
Lance M.
The price is ￥13,705
￥45,060 total
includes taxes & fees
Dec 17 - Dec 18
Hunts Bend Private Getaway!
Dining
A Kentucky Cabin - Cozy Secluded Cabin One Mile From Mammoth Cave National Park

Cabin in Park City

A Kentucky Cabin - Cozy Secluded Cabin One Mile From Mammoth Cave National Park
9.8 out of 10, Exceptional, (13)
"Had a great time staying at this unique property."
United States
Andrew
The price is ￥31,148
￥53,223 total
includes taxes & fees
Dec 12 - Dec 13
A Kentucky Cabin - Cozy Secluded Cabin One Mile From Mammoth Cave National Park
Exterior
Peaceful 2-bedroom home near Mammoth Cave.

Vacation Home in Cave City

Peaceful 2-bedroom home near Mammoth Cave.
10.0 out of 10, Exceptional, (21)
"Good stay, communication good, gave great recommendations on local attractions. "
United States
Anonymous traveler
The price is ￥11,150
￥20,071 total
includes taxes & fees
Dec 18 - Dec 19
Peaceful 2-bedroom home near Mammoth Cave.
Outdoor dining
Country setting with mature trees, large deck. Game/Rec room, Fire Pit and Grill

Vacation Home in Austin

Country setting with mature trees, large deck. Game/Rec room, Fire Pit and Grill
10.0 out of 10, Exceptional, (16)
"Lovely stay on a beautiful property!"
United States
Christine G.
The price is ￥18,689
￥36,225 total
includes taxes & fees
Dec 14 - Dec 15
Country setting with mature trees, large deck. Game/Rec room, Fire Pit and Grill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakland Hotel Reviews

Drury Inn & Suites Bowling Green

Drury Inn & Suites Bowling Green

10/10 Excellent
"Staff was wonderful! Very impressed with all the amenities! Will be staying a Drury in the future! "
Amanda 1-night trip
Posted 3 days ago
Drury Inn & Suites Bowling Green

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

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Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, we have vacation rentals near top local attractions in Oakland, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation rentals that Oakland has to offer?

Peaceful private 3 BR new home near Mammoth Cave.: This vacation home rental outside of Oakland offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Oakland?

While exploring the area, visit family-friendly sights like Beech Bend Park, or get outside and enjoy nature at Fountain Square Park. National Corvette Museum and NCM Motorsports Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Oakland?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Oakland. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.