A sandy beach with a rocky shoreline, trees with autumn foliage, and a lake under a partly cloudy sky.

Find Hotels with a Pool in Oakland, MD

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Check availability on Oakland Hotels with a Pool

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Oakland hotels with a pool

A modern lodge with a pool, outdoor seating, and a scenic lake view.

1. Cove Creek Lodge

Cove Creek Lodge
2.0 star property
Oakland
8.8 out of 10, Excellent, (3 reviews)
$146 nightly
The price is $167
Oct 29 - Oct 30
Total with taxes and fees
Cove Creek Lodge
Pool

2. Will O' The Wisp: 205A Efficiency/One Bath

Will O' The Wisp: 205A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (14 reviews)
$253 nightly
The price is $286
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 205A Efficiency/One Bath
Pool

3. Will O' The Wisp: 302B One Bedroom/One Bath

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
10.0 out of 10, Exceptional, (1 review)
$260 nightly
The price is $294
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 302B One Bedroom/One Bath
Pool

4. Will O' The Wisp: 107B One Bedroom/One Bath

Will O' The Wisp: 107B One Bedroom/One Bath
Mountainside
10.0 out of 10, Exceptional, (3 reviews)
  • cleanliness
    Lakeside getaway invites relaxation with heated indoor pool and hot tub, plus nearby outdoor adventures on Deep Creek Lake.
$275 nightly
The price is $311
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 107B One Bedroom/One Bath
Pool

5. Will O' The Wisp: 206A Efficiency/One Bath

Will O' The Wisp: 206A Efficiency/One Bath
Oakland
9.2 out of 10, Wonderful, (17 reviews)
  • cleanliness
    Mountain condo offers indoor heated pool and hot tub with panoramic nature views for total relaxation.
$253 nightly
The price is $286
Nov 15 - Nov 16
Total with taxes and fees
Will O' The Wisp: 206A Efficiency/One Bath
Pool

6. Will O' The Wisp: 102B One Bedroom/One Bath

Will O' The Wisp: 102B One Bedroom/One Bath
Oakland
9.6 out of 10, Exceptional, (5 reviews)
$254 nightly
The price is $287
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 102B One Bedroom/One Bath
Pool

7. Will O' The Wisp: 105A Efficiency/One Bath

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (26 reviews)
$253 nightly
The price is $286
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 105A Efficiency/One Bath
Pool

8. Will O' The Wisp: 103A Efficiency/One Bath

Will O' The Wisp: 103A Efficiency/One Bath
Oakland
9.4 out of 10, Exceptional, (13 reviews)
$254 nightly
The price is $287
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 103A Efficiency/One Bath
Pool

9. Will O' The Wisp: 104B One Bedroom/One Bath

Will O' The Wisp: 104B One Bedroom/One Bath
Oakland
10.0 out of 10, Exceptional, (2 reviews)
  • cleanliness
    Lakeside condo offers indoor pool, hot tub, and sauna, with nearby kayaking and snowboarding options.
$274 nightly
The price is $310
Nov 18 - Nov 19
Total with taxes and fees
Will O' The Wisp: 104B One Bedroom/One Bath
Pool

10. Will O' The Wisp: 204B One Bedroom/One Bath

Will O' The Wisp: 204B One Bedroom/One Bath
Oakland
9.4 out of 10, Exceptional, (6 reviews)
$257 nightly
The price is $291
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 204B One Bedroom/One Bath
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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Choose what matters most at hotels with a pool in Oakland

Breakfast included
Hot tub

Hotels with pools and hot tubs in Oakland

Pool
Will O' The Wisp: 208B One Bedroom/One Bath

Will O' The Wisp: 208B One Bedroom/One Bath

Will O' The Wisp: 208B One Bedroom/One Bath
Oakland
9.4 out of 10, Exceptional, (3)
$263 nightly
The price is $298
Oct 28 - Oct 29
Total with taxes and fees
Will O' The Wisp: 208B One Bedroom/One Bath
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.
View all properties

Top Oakland Hotel Reviews

Frequently asked questions

What are the best hotels in Oakland with outdoor pools?
Cove Creek Lodge is an excellent choice for travellers seeking a memorable stay in Oakland, featuring an inviting outdoor pool that enhances the overall experience. This lodge stands out not just for its shared pool, but also for its stunning mountain views and proximity to a picturesque lake, making it a fantastic spot for travellers.

With a superb review rating of 10.0, the Cove Creek Lodge offers a range of accommodations, including the Standard Double Queen Fireplace Room and the Poolside Double Queen Fireplace Room, both of which promise a cozy atmosphere and access to the pool. Guests appreciate the clean rooms and comfort of the beds, making it a family-friendly option that caters to both relaxation and outdoor activities.

Moreover, the lodge's location is ideal for those who enjoy mountain climbing and biking, with opportunities for exploration right at your doorstep.
How much does a hotel with outdoor pool in Oakland cost?
Enjoy staying in a hotel in Oakland with an outdoor pool. You can find a great deal from $124 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Is it cheaper to book flights and a Oakland hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Oakland for you.

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