Entire home
New! Captain Jack's: Lake Access, Dock Slip, Hot Tub!
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Reviews
10 out of 10
Exceptional
5 bedrooms 5 bathrooms Sleeps 14 378.7 sq m
Popular amenities
Explore the area

Oakland, MD
- Deep Creek Lake4 min drive
- Wisp Resort12 min drive
- Deep Creek Lake State Park13 min drive
- Oakland, MD (ODM-Garrett County)14 min drive
Rooms & beds
5 bedrooms (sleeps 14)
Lower Level: Bedroom
2 Single Bunk Beds
Lower Level: Sitting Room
2 Double Sofa Beds
Main Level: Bedroom (Suite)
1 King Bed
Main Level: Office Space
2 Single Beds
Upper Level: Bedroom 1 (Suite)
1 King Bed
Upper Level: Bedroom 2
1 King Bed
Upper Level: Bedroom 3
1 Queen Bed
5 bathrooms
Lower Level: Bath
Shower only
Main Level: Attached Bath
Shower only
Main Level: Bath
Bathtub or shower
Upper Level: Attached Bath
Bathtub or shower
Upper Level: Bath
Bathtub or shower
Spaces
Deck or patio
Kitchen
Balcony
Dining area
About this property
New! Captain Jack's: Lake Access, Dock Slip, Hot Tub!
Name: Captain Jack's | Bedrooms: 5 | Bathrooms: 5 | Sleeps: 14 | Access: Lake Access | Pets Not Permitted | MUST BE 24+ YEARS TO RENT | Free WIFI Provided
DESCRIPTION:
Land Ho!
A paradise vacation awaits at Captain Jack’s! Step inside this mountain retreat and take in the amazing wall of windows and stunning stone fireplace that gives this home a sense of warmth and comfort. This “wow factor” great room is the perfect place for family gatherings and entertaining large groups. Gather everyone around the rustic farmhouse dining table for a home cooked meal and plan your adventure filled days ahead. Classic hardwood floors guide you through the open floor plan of the main level and out onto the deck overlooking the woodsy back yard. What wildlife will you spot during your stay? Relax on the deck and soak up the afternoon and check for visitors or enjoy an evening drink, take in the fresh mountain air, and watch the sunset. With multiple spaces to do some work from home and an amazing lower level game area equipped with a full bar and multiple games, you can work and play all day long! Enjoy a day on the lake with the use of your designated dock and community lake access and after, relax in the bubbles of the hot tub or enjoy some s’mores around the campfire. With the amazing home amenities, close proximity to community amenities (the tennis courts are right across the street!) and the lake right at the bottom of the hill, this home has a little something for everyone! So get underway! Climb aboard, anchor down, and enjoy your smooth sailing vacation at Captain Jack’s!
ACCESS DETAILS:
Lake access and dock slip are located at the Mountainside Marina Club located off of Route 219, next to the Lakeside Creamery. Please note that docks are only guaranteed from Memorial Day through Labor Day.
COMMUNITY/AREA DETAILS:
This home is located in the Mountainside Community at Deep Creek Lake.
This home comes with free access to the Community Aquatic Recreation Center (CARC)! This fitness and wellness complex, located in the central Deep Creek Lake area, offers a modern gym and a full-size indoor pool. The free CARC membership is available to all guests in the home for the duration of your stay, up to the home’s full occupancy.
LAYOUT DETAILS:
Main Level:
- Kitchen
- Great Room with Dining Space
- Dining Room
- Full Bath with Shower/Tub
- Bedroom (Suite): King Bed, Attached Bath with Shower
- Office Space: Daybed with Trundle
- Laundry
Upper Level:
- Loft
- Bedroom (Suite): King Bed Attached Bath with Shower/Tub
- Full Bath with Shower/Tub
- Bedroom: King Bed
- Bedroom: Queen Bed
Lower Level:
- Den: Game Area and Bar
- Full Bath with Shower
- Bedroom: 2 Duo Bunk Beds
- Sitting Room: Queen Sleeper Sofa
DISCLAIMERS:
4WD/AWD or snow tires are always recommended for the area during the Winter months of November – March. For more house specific driveway information, please refer to your app/guest portal after booking.
AFTER BOOKING: An email will be sent to the address provided during check-out; please check for action items needed to secure your reservation. The subject of this email will start with "URGENT: Complete Your Booking For"... and may be in your Promotional/Marketing folders depending on your email provider and settings.
TOILETRIES & PAPER PRODUCTS: Bed linens and bath towels provided w/rental. No soaps, toiletries, paper products, trash bags, etc. will be provided with the exception of a welcome bag including a few starter items. Please pack accordingly.
NOTE: A copy of the contract holder's Photo ID, a signed contract, and a list of your full travel party (names/ages of all attending) will be required to complete your booking. If booking last minute, you may be required to stop by our main office to show your photo ID and the credit card used on the reservation. This policy is in place to help combat fraudulent activity that is more likely to occur in last-minute arrivals.
DESCRIPTION:
Land Ho!
A paradise vacation awaits at Captain Jack’s! Step inside this mountain retreat and take in the amazing wall of windows and stunning stone fireplace that gives this home a sense of warmth and comfort. This “wow factor” great room is the perfect place for family gatherings and entertaining large groups. Gather everyone around the rustic farmhouse dining table for a home cooked meal and plan your adventure filled days ahead. Classic hardwood floors guide you through the open floor plan of the main level and out onto the deck overlooking the woodsy back yard. What wildlife will you spot during your stay? Relax on the deck and soak up the afternoon and check for visitors or enjoy an evening drink, take in the fresh mountain air, and watch the sunset. With multiple spaces to do some work from home and an amazing lower level game area equipped with a full bar and multiple games, you can work and play all day long! Enjoy a day on the lake with the use of your designated dock and community lake access and after, relax in the bubbles of the hot tub or enjoy some s’mores around the campfire. With the amazing home amenities, close proximity to community amenities (the tennis courts are right across the street!) and the lake right at the bottom of the hill, this home has a little something for everyone! So get underway! Climb aboard, anchor down, and enjoy your smooth sailing vacation at Captain Jack’s!
ACCESS DETAILS:
Lake access and dock slip are located at the Mountainside Marina Club located off of Route 219, next to the Lakeside Creamery. Please note that docks are only guaranteed from Memorial Day through Labor Day.
COMMUNITY/AREA DETAILS:
This home is located in the Mountainside Community at Deep Creek Lake.
This home comes with free access to the Community Aquatic Recreation Center (CARC)! This fitness and wellness complex, located in the central Deep Creek Lake area, offers a modern gym and a full-size indoor pool. The free CARC membership is available to all guests in the home for the duration of your stay, up to the home’s full occupancy.
LAYOUT DETAILS:
Main Level:
- Kitchen
- Great Room with Dining Space
- Dining Room
- Full Bath with Shower/Tub
- Bedroom (Suite): King Bed, Attached Bath with Shower
- Office Space: Daybed with Trundle
- Laundry
Upper Level:
- Loft
- Bedroom (Suite): King Bed Attached Bath with Shower/Tub
- Full Bath with Shower/Tub
- Bedroom: King Bed
- Bedroom: Queen Bed
Lower Level:
- Den: Game Area and Bar
- Full Bath with Shower
- Bedroom: 2 Duo Bunk Beds
- Sitting Room: Queen Sleeper Sofa
DISCLAIMERS:
4WD/AWD or snow tires are always recommended for the area during the Winter months of November – March. For more house specific driveway information, please refer to your app/guest portal after booking.
AFTER BOOKING: An email will be sent to the address provided during check-out; please check for action items needed to secure your reservation. The subject of this email will start with "URGENT: Complete Your Booking For"... and may be in your Promotional/Marketing folders depending on your email provider and settings.
TOILETRIES & PAPER PRODUCTS: Bed linens and bath towels provided w/rental. No soaps, toiletries, paper products, trash bags, etc. will be provided with the exception of a welcome bag including a few starter items. Please pack accordingly.
NOTE: A copy of the contract holder's Photo ID, a signed contract, and a list of your full travel party (names/ages of all attending) will be required to complete your booking. If booking last minute, you may be required to stop by our main office to show your photo ID and the credit card used on the reservation. This policy is in place to help combat fraudulent activity that is more likely to occur in last-minute arrivals.
Property manager
Railey Vacations
Premier Host
Languages
English
Add dates for prices
Amenities
Hot tub
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
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House Rules
Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
We should mention
A car is required for transport to and from this property
About the area
Oakland
Located in Mountainside, a neighbourhood in Oakland, this holiday home is in a rural area and on a lake. While the natural beauty of Deep Creek Lake and Deep Creek Lake State Park can be enjoyed by anyone, those looking for an activity can explore Wisp Resort.
Funland and Baltimore and Ohio Railroad Station are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Oakland, MD
What's nearby
- Deep Creek Lake - 4 min drive - 2.3 km
- Wisp Resort - 12 min drive - 10.3 km
- Deep Creek Lake State Park - 13 min drive - 8.9 km
- Lodestone Golf Club - 14 min drive - 11.9 km
- Swallow Falls State Park - 16 min drive - 13.0 km
Getting around
Restaurants
- Arrowhead Market - 5 min drive
- McDonald's - 5 min drive
- Deep Creek Yacht Club Turkey Neck - 24 min drive
- UNO Pizzeria & Grill - 4 min drive
- Trader's Coffee House - 3 min drive
Frequently asked questions
Reviews
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About the host
Hosted by Railey Vacations

Railey Vacations is Deep Creek's #1 vacation rental provider. With over 35 years of experience, and more than 400 properties, we are here to get you into the perfect home for your next Deep Creek Lake vacation!
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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