Photo by KM Moore
Find Hotels with a Pool in Oakland, MD
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Oakland Hotels with a Pool
Pick from Oakland Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.
Frequently asked questions
Find More Hotels near Oakland
More Hotel Options in Oakland
- Adventure Hotels (3)
- Beach Hotels (1)
- Business Hotels (1)
- Family Hotels (5)
- Golf Hotels (1)
- Historic Hotels (1)
- Hotel Wedding Venues (1)
- Hotel with a Concierge (1)
- Hotels with Bars (1)
- Hotels with Free Parking (3)
- Hotels with Hot Tubs (1)
- Hotels with WiFi (3)
- Luxury Hotels (1)
- Pet-friendly Hotels (2)
- Resorts & Hotels with Spas (1)
- Romantic Hotels (2)
- Shopping Hotels (1)
- Ski Hotels (3)
More Accommodation Types in Oakland
- Vacation Homes in Maryland (4,599)
- Condo Rentals in Maryland (4,203)
- Apartments in Maryland (1,017)
- Cabin Rentals in Maryland (326)
- Cottages in Maryland (326)
- Motels in Maryland (89)
- Aparthotels in Maryland (66)
- B&B in Maryland (63)
- Guest Houses in Maryland (44)
- Chalets in Maryland (27)
- Farmstay in Maryland (25)
- Villas in Maryland (25)
- Resorts in Maryland (22)
- Houseboats in Maryland (16)
- RV Parks in Maryland (12)
- Inns in Maryland (6)
- Town Houses in Maryland (6)
- Lodges in Maryland (3)
- Hostels in Maryland (2)
- Castles in Maryland (1)
- Condo Resorts in Maryland (1)
- Holiday Park Resorts in Maryland (1)
- Residences in Maryland (1)
Hotels near popular Oakland Attractions
- Hotels near Deep Creek Lake
- Hotels near Swallow Falls State Park
- Hotels near Blackwater Falls State Park
- Hotels near Deep Creek Lake State Park
- Hotels near Ohiopyle State Park
- Hotels near Wisp Resort
- Hotels near Canaan Valley Ski Resort
- Hotels near Coopers Rock State Forest
- Hotels near Blackwater Falls
- Hotels near Dolly Sods Wilderness Area
Oakland Hotels by Star Rating
Explore more hotels
- Adorable adventure cabin in the woods with full kitchen, firepit, & porch
- Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck
- Charming home with furnished deck & lake view - walking distance to shops
- Dog-friendly home in a great, central location w/ private hot tub & golf nearby
- Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger
- Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table
- New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit
- Lakefront/Dock/Amazing views HotTub
- Amazing Central Location! Lakefront! Hot tub/dock!
- New! Serenity Shores: Lake Area, Hot Tub, Fireplace, Fire Pit, A/C!
- Suites at Silver Tree A314: Studio and Loft Suite with Free WIFI and Fireplace!
- New: Lakefront Luxury Home with Private Indoor Heated Pool!
- The Herrington: Largest Rental In MD, Indoor Pool, Home Theater
- The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!
- Private cabin with hot tub, outdoor dining, and fireplace
- Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
- Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip
- Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
- Three Bedroom Cabin, Hot Tub, Wooded Lot, Access to Lake, Family, Pet Friendly.
- Lake It Easy: Lake Access, Fireplace, Wifi, Lake Views!