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Find Hotels with a Pool in Oakland, MD

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Check availability on Oakland Hotels with a Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Oakland hotels with a pool

Pool
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
Beach
A balcony with a view of a lake, two white chairs, and a stone floor.

1. Will O' The Wisp: 512G Two Bedroom/One Bath

Will O' The Wisp: 512G Two Bedroom/One Bath
Oakland
￥44,704
￥57,472 total
includes taxes & fees
Oct 2 - Oct 3
Will O' The Wisp: 512G Two Bedroom/One Bath
Pool
Exterior
Living area
Beach

2. Will O' The Wisp: 508G Two Bedroom/One Bath

Will O' The Wisp: 508G Two Bedroom/One Bath
Mountainside
  • Indoor pool retreat with hot tub and sauna near Deep Creek Lake offers year-round adventures.
￥44,704
￥57,472 total
includes taxes & fees
Oct 2 - Oct 3
Will O' The Wisp: 508G Two Bedroom/One Bath
Pool
Beach
A balcony with a glass table and two chairs, overlooking a marina with boats and a lake.
Exterior

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

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
￥36,233
￥46,645 total
includes taxes & fees
Oct 28 - Oct 29
Will O' The Wisp: 302B One Bedroom/One Bath
Pool
Beach
A patio with two patterned chairs and a small table, overlooking a lake with boats and trees.
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.

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

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
￥35,203
￥45,304 total
includes taxes & fees
Oct 28 - Oct 29
Will O' The Wisp: 105A Efficiency/One Bath
Pool
Beach
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
Exterior

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

Will O' The Wisp: 103A Efficiency/One Bath
Oakland
￥35,548
￥45,699 total
includes taxes & fees
Oct 2 - Oct 3
Will O' The Wisp: 103A Efficiency/One Bath
Pool
Beach
A room with a blue checkered sofa, a grey sofa with patterned cushions, a wooden bench, and a view of the outdoors through a sliding glass door.
Exterior

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

Will O' The Wisp: 102B One Bedroom/One Bath
Oakland
￥36,772
￥46,926 total
includes taxes & fees
Oct 4 - Oct 5
Will O' The Wisp: 102B One Bedroom/One Bath
Pool
Beach
A glass table with four chairs, a black metal railing, and a view of a body of water and trees.
Exterior

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

Will O' The Wisp: 206A Efficiency/One Bath
Oakland
  • Mountain condo offers indoor heated pool and hot tub with panoramic nature views for total relaxation.
￥35,203
￥45,304 total
includes taxes & fees
Oct 7 - Oct 8
Will O' The Wisp: 206A Efficiency/One Bath
Pool
A bedroom with a large bed, a ceiling fan, a nightstand with a lamp, and a view of a lake through the window.
Exterior
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.

8. Will O' The Wisp: 708H Studio Loft/One Bath

Will O' The Wisp: 708H Studio Loft/One Bath
Oakland
￥35,384
￥45,178 total
includes taxes & fees
Oct 4 - Oct 5
Will O' The Wisp: 708H Studio Loft/One Bath
Pool
A balcony with a view of a lake, dock, and beach.
A modern living room with a fireplace, a sofa, a bench, and a view of the outdoors.
Exterior

9. Will O' The Wisp: 301D Two Bedroom/Two Bath

Will O' The Wisp: 301D Two Bedroom/Two Bath
Oakland
￥55,519
￥70,801 total
includes taxes & fees
Oct 14 - Oct 15
Will O' The Wisp: 301D Two Bedroom/Two Bath
Pool
A lakeside view with a dock, boats, and a sandy beach area.
Exterior
A balcony with a table and chairs, overlooking a lake and a beach.

10. Will O' The Wisp: 203A Efficiency/One Bath

Will O' The Wisp: 203A Efficiency/One Bath
Oakland
￥35,203
￥44,970 total
includes taxes & fees
Oct 4 - Oct 5
Will O' The Wisp: 203A Efficiency/One Bath
View all properties

Choose what matters most at hotels with a pool in Oakland

Breakfast included
Hot tub
4 stars
5 stars
Spa

Hotels with pools and hot tubs in Oakland

Exterior
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
A modern hotel room with a grey sofa, a bed with a grey patterned bedspread, a small table with a remote control, and framed pictures on the wall.
Beach

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

Will O' The Wisp: 206A Efficiency/One Bath
Oakland
￥35,203
￥45,304 total
includes taxes & fees
Oct 7 - Oct 8
Will O' The Wisp: 206A Efficiency/One Bath
A balcony with a glass table and two chairs, overlooking a marina with boats and a lake.
Spa
Exterior
Pool

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

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
￥36,233
￥46,645 total
includes taxes & fees
Oct 28 - Oct 29
Will O' The Wisp: 302B One Bedroom/One Bath
Exterior
Beach
A dining area with a wooden table and chairs, a brick accent wall, and pendant lighting.
A modern living room with a large TV, white furniture, and a view of the outdoors.

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

Will O' The Wisp: 107B One Bedroom/One Bath
Mountainside
￥40,341
￥51,830 total
includes taxes & fees
Oct 28 - Oct 29
Will O' The Wisp: 107B One Bedroom/One Bath
A view from a porch overlooking a lake with a dock, benches, and a stone wall.
A modern living room with a sofa, a dining area with a table and chairs, a large wall clock, and a sign that reads 'Our Happy Place'.
Pool
Beach

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

Will O' The Wisp: 103A Efficiency/One Bath
Oakland
￥35,548
￥45,699 total
includes taxes & fees
Oct 2 - Oct 3
Will O' The Wisp: 103A Efficiency/One Bath
Exterior
Beach
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
Spa

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

Will O' The Wisp: 205A Efficiency/One Bath
Oakland
￥35,203
￥44,970 total
includes taxes & fees
Oct 4 - Oct 5
Will O' The Wisp: 205A Efficiency/One Bath
Exterior
Pool
Beach
A living room with a fireplace, a sofa, a coffee table, and a dining area in the background.

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

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
￥35,203
￥45,304 total
includes taxes & fees
Oct 28 - Oct 29
Will O' The Wisp: 105A Efficiency/One Bath
Exterior
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
Spa
Beach

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

Will O' The Wisp: 102B One Bedroom/One Bath
Oakland
￥36,772
￥46,926 total
includes taxes & fees
Oct 4 - Oct 5
Will O' The Wisp: 102B One Bedroom/One Bath
Exterior
A modern living room with a dining area, featuring a wooden table and chairs, a sofa, and a TV on a stand.
Pool
Beach

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

Will O' The Wisp: 104B One Bedroom/One Bath
Oakland
￥38,215
￥49,238 total
includes taxes & fees
Oct 5 - Oct 6
Will O' The Wisp: 104B One Bedroom/One Bath
Exterior
A balcony with a view of a lake, a table, and two chairs.
A modern living room with a sofa, armchairs, a glass coffee table, and a dining area with a table and chairs.
Pool

Will O' The Wisp: 304C One Bedroom/One Bath

Will O' The Wisp: 304C One Bedroom/One Bath
Oakland
￥41,707
￥53,242 total
includes taxes & fees
Oct 15 - Oct 16
Will O' The Wisp: 304C One Bedroom/One Bath
Exterior
Pool
Beach
A bedroom with a large bed, a ceiling fan, a nightstand with a lamp, and a view of a lake through the window.

Will O' The Wisp: 708H Studio Loft/One Bath

Will O' The Wisp: 708H Studio Loft/One Bath
Oakland
￥35,384
￥45,178 total
includes taxes & fees
Oct 4 - Oct 5
Will O' The Wisp: 708H Studio Loft/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's it like visiting Oakland?
If taking it easy by the pool is your idea of the perfect getaway, you may want to consider luxurious Oakland, which has 29 places to stay with pools. During your trip, you can explore sights such as Deep Creek Lake, and then relax and unwind poolside at one of the accommodations in Oakland that travelers like for their pools.
What are some accommodations with pools in Oakland?
Baja Motel: Vacation home located near Deep Creek Lake. Provides complimentary wireless internet access, a communal pool, and kitchens. The Garrett Inn: Vacation home, 5-minute walk from Deep Creek Lake. Offers kitchens, a communal pool, and televisions. Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp: Vacation home located near Deep Creek Lake. Features kitchens, a pool, and televisions. In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,: Vacation home, 11-minute walk from Deep Creek Lake. Offers complimentary wireless internet access, a communal pool, and kitchens. Dog Friendly Cabin in the Woods, Hot Tub & Firepit: Vacation home located near Deep Creek Lake. Provides complimentary wireless internet access, a communal pool, and kitchens.
How many pool hotels will I be able to find in Oakland?
Expedia's 29 hotels in Oakland give you a great choice for your poolside getaway.
What is there to see and do in Oakland?
Explore places like Deep Creek Lake while you're in Oakland. Spend some time experiencing the great outdoors at Youghiogheny River and Broadford Park. Take in the natural beauty of Oakland with the lakeside setting and riverfront.
When is the best time to book a hotel with a pool in Oakland?
Taking into account the local weather in Oakland can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Oakland are January, December, February, and May, with each month seeing an average of 31 inches of snowfall.

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