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Oakland Hotel Guide - Hotels with Pool in Oakland, Maryland

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Check availability on Oakland Hotels with Pool

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Oakland hotels with a pool

Pool
A compact kitchen with dark cabinets, a stainless steel dishwasher, a microwave, and a toaster.
A hotel room with a bed, a sofa, a wooden floor, and a kitchenette in the background.
A modern bathroom with a round mirror, a sink, a toilet, and a glass-enclosed shower.

1. Cove Creek Lodge

Cove Creek Lodge
Oakland
€189
includes taxes & fees
25 Oct - 26 Oct
Cove Creek Lodge
Pool
Exterior
Beach
A glass table with four chairs, a black metal railing, and a view of a body of water and trees.

2. 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.
€263
includes taxes & fees
6 Oct - 7 Oct
Will O' The Wisp: 206A Efficiency/One Bath
Pool
A view from a balcony overlooking a lake with boats docked at a pier, a sandy beach, and a grassy area with benches.
Beach
Exterior

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

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
€271
includes taxes & fees
12 Oct - 13 Oct
Will O' The Wisp: 302B One Bedroom/One Bath
Pool
A modern living room with a large TV, white furniture, and a view of the outdoors.
A dining area with a wooden table and chairs, a brick accent wall, and pendant lighting.
Exterior

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

Will O' The Wisp: 107B One Bedroom/One Bath
Mountainside
  • Lakeside getaway invites relaxation with heated indoor pool and hot tub, plus nearby outdoor adventures on Deep Creek Lake.
€285
includes taxes & fees
29 Oct - 30 Oct
Will O' The Wisp: 107B One Bedroom/One Bath
Pool
A balcony with a table and chairs, overlooking a lake with trees and a dock.
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
Exterior

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

Will O' The Wisp: 205A Efficiency/One Bath
Oakland
€263
includes taxes & fees
6 Oct - 7 Oct
Will O' The Wisp: 205A Efficiency/One Bath
Pool
Exterior
Beach
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.

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

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
€259
includes taxes & fees
28 Oct - 29 Oct
Will O' The Wisp: 105A Efficiency/One Bath
Pool
Exterior
Beach
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.

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

Will O' The Wisp: 103A Efficiency/One Bath
Oakland
€264
includes taxes & fees
8 Oct - 9 Oct
Will O' The Wisp: 103A Efficiency/One Bath
Pool
Exterior
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
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.

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

Will O' The Wisp: 102B One Bedroom/One Bath
Oakland
€270
includes taxes & fees
5 Oct - 6 Oct
Will O' The Wisp: 102B One Bedroom/One Bath
Pool
A modern living room with a dining area, featuring a wooden table and chairs, a sofa, and a TV on a stand.
Beach
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.

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

Will O' The Wisp: 104B One Bedroom/One Bath
Oakland
  • Lakeside condo offers indoor pool, hot tub, and sauna, with nearby kayaking and snowboarding options.
€280
includes taxes & fees
5 Oct - 6 Oct
Will O' The Wisp: 104B One Bedroom/One Bath
Pool
A room with a dining table, bench, sofa, and a staircase.
Exterior
Beach

10. Will O' The Wisp: 710H Studio Loft/One Bath

Will O' The Wisp: 710H Studio Loft/One Bath
Oakland
€260
includes taxes & fees
5 Oct - 6 Oct
Will O' The Wisp: 710H Studio Loft/One Bath
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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
Beach
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.

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

Will O' The Wisp: 206A Efficiency/One Bath
Oakland
€263
includes taxes & fees
6 Oct - 7 Oct
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.
Beach
Spa
Pool

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

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
€296
includes taxes & fees
18 Oct - 19 Oct
Will O' The Wisp: 302B One Bedroom/One Bath
Exterior
A modern living room with a large TV, white furniture, and a view of the outdoors.
A dining area with a wooden table and chairs, a brick accent wall, and pendant lighting.
Pool

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

Will O' The Wisp: 107B One Bedroom/One Bath
Mountainside
€285
includes taxes & fees
29 Oct - 30 Oct
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.
Beach
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

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

Will O' The Wisp: 103A Efficiency/One Bath
Oakland
€264
includes taxes & fees
8 Oct - 9 Oct
Will O' The Wisp: 103A Efficiency/One Bath
Exterior
Spa
Pool
Beach

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

Will O' The Wisp: 205A Efficiency/One Bath
Oakland
€263
includes taxes & fees
6 Oct - 7 Oct
Will O' The Wisp: 205A Efficiency/One Bath
Exterior
A patio with two patterned chairs and a small table, overlooking a lake with boats and trees.
Pool
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
€259
includes taxes & fees
28 Oct - 29 Oct
Will O' The Wisp: 105A Efficiency/One Bath
Exterior
Beach
Pool
Spa

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

Will O' The Wisp: 102B One Bedroom/One Bath
Oakland
€270
includes taxes & fees
5 Oct - 6 Oct
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
€280
includes taxes & fees
5 Oct - 6 Oct
Will O' The Wisp: 104B One Bedroom/One Bath
Exterior
A modern living room with a sofa, armchairs, a glass coffee table, and a dining area with a table and chairs.
Pool
Beach

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

Will O' The Wisp: 304C One Bedroom/One Bath
Oakland
€279
includes taxes & fees
18 Oct - 19 Oct
Will O' The Wisp: 304C One Bedroom/One Bath
Exterior
A bedroom with a large bed, a ceiling fan, a nightstand with a lamp, and a view of a lake through the window.
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.
Pool

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

Will O' The Wisp: 708H Studio Loft/One Bath
Oakland
€260
includes taxes & fees
5 Oct - 6 Oct
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.
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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. While you're visiting, you can explore sights such as Deep Creek Lake, and then take it easy poolside at one of the accommodation options in Oakland that travellers like for their pools.
What are some accommodation options with pools in Oakland?
Baja Motel: Holiday home located near Deep Creek Lake. Provides complimentary wireless Internet access, a communal pool and kitchens. The Garrett Inn: Holiday 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: Holiday 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,: Holiday 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: Holiday home located near Deep Creek Lake. Provides complimentary wireless Internet access, a communal pool and kitchens.
How many hotels with pools will I 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 such as 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 the local weather in Oakland into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Oakland are January, December, February and May, with each month seeing an average of 79 cm of snowfall.