10/10 Excellent
Juliann D.
18 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Juliann D.
Stayed 1 night in Aug 2025
Chalet
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Family-friendly chalet in Oakland with a hot tub
Photo gallery for Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Reviews
10 out of 10
Exceptional
4 bedrooms4+ bathroomsSleeps 12
Popular amenities
Explore the area
Oakland, MD
- Place, Wisp Resort
- Place, Deep Creek Lake2 min drive
- Place, Deep Creek Lake State Park10 min drive
Rooms & beds
4 bedrooms (sleeps 12)
Basement Bedroom
1 Queen Bed
Living Room 1
1 Double Sofa Bed
Main Floor Primary en Suite Bath
1 King Bed
Office 1
2 Single Beds
Upstairs Bedroom
1 Queen Bed
Upstairs Bedroom en Suite Bath
1 Queen Bed
4 bathrooms, 1 half bathroom
Basement Bathroom
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Main Floor Powder Room
Soap · Towels provided · Toilet
Primary Bedroom en Suite Bath
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Upstairs Bedroom en Suite Bath
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Upstairs Hall Bath
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Spaces
Deck or patio
Kitchen
Separate dining area
Dining area
About this property
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Welcome to The Lookout, your comfy Deep Creek Lake retreat! Whether you're gathering family, celebrating with friends, or planning a special couples' getaway, our vacation home offers an ideal homebase for small groups exploring DCL. Perched above the lake in the central “Trader’s Landing” location, you’re only minutes away from area favorites: boating, hiking, breweries, good eats, and more!
Mike and I are avid travelers and nature lovers, so much of The Lookout is designed to bring the outdoors in (the massive windows definitely help!). We hope this nod to nature helps you and your crew feel happy and relaxed, while equally tempted to go outside to adventure and play!
Start your mornings with coffee on the expansive deck as the sun rises over the water. Mike loves a BIG family breakfast, so the kitchen is well-stocked for groups, including large platters to serve family-style, a second fridge for drinks, and kid-friendly dishware.
Sleep soundly in buttery-soft PeachSkin sheets (you’ll thank us later) and your pick from our “pillow menu,” a luxury Danielle first experienced at a fancy-pants hotel in Europe.
Entertainment awaits in the game room—battle it out over ping pong or foosball, or dive into 50+ board games on the digital Infinity game table. Rainy day? Cozy up for movie night on the massive 72” TV, or step into the HOT TUB under string lights and starlit skies.
For a quiet escape, retreat to the library loft, where a take-one/leave-one book collection and a secluded area invite relaxation. Our particular favorite is the lookout loft, a magical hideaway with cushy seating at the top of the spiral staircase. Play music, unwind with the gaming system, or simply soak in the vibes.
Your comfort and enjoyment are our priority—we can’t wait to host you at The Lookout!
Mike and I are avid travelers and nature lovers, so much of The Lookout is designed to bring the outdoors in (the massive windows definitely help!). We hope this nod to nature helps you and your crew feel happy and relaxed, while equally tempted to go outside to adventure and play!
Start your mornings with coffee on the expansive deck as the sun rises over the water. Mike loves a BIG family breakfast, so the kitchen is well-stocked for groups, including large platters to serve family-style, a second fridge for drinks, and kid-friendly dishware.
Sleep soundly in buttery-soft PeachSkin sheets (you’ll thank us later) and your pick from our “pillow menu,” a luxury Danielle first experienced at a fancy-pants hotel in Europe.
Entertainment awaits in the game room—battle it out over ping pong or foosball, or dive into 50+ board games on the digital Infinity game table. Rainy day? Cozy up for movie night on the massive 72” TV, or step into the HOT TUB under string lights and starlit skies.
For a quiet escape, retreat to the library loft, where a take-one/leave-one book collection and a secluded area invite relaxation. Our particular favorite is the lookout loft, a magical hideaway with cushy seating at the top of the spiral staircase. Play music, unwind with the gaming system, or simply soak in the vibes.
Your comfort and enjoyment are our priority—we can’t wait to host you at The Lookout!
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 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
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 no carbon monoxide detector on the property, but there are gas appliances; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
About the area
Oakland
Oakland is home to this chalet. 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.
Travelling with kids? Consider Funland and Baltimore and Ohio Railroad Station. Take in the nearby slopes with snowboarding and skiing, or try out other outdoor activities such as snowmobiling and sledging.
Oakland, MD
What's nearby
- Deep Creek Lake - 2 min drive - 2.1 km
- Funland - 5 min drive - 5.5 km
- Adventure Sports Center International - 9 min drive - 8.3 km
- Deep Creek Lake State Park - 10 min drive - 4.9 km
- Lodestone Golf Club - 11 min drive - 9.6 km
Restaurants
- McDonald's - 4 min drive
- Burger King - 5 min drive
- Casselman Bakery and Café - 3 min drive
- UNO Pizzeria & Grill - 3 min drive
- Perkins American Food Co. - 6 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.6/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Nicole N.
30 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nicole N.
Stayed 4 nights in Oct 2025
10/10 Excellent
Lori S.
8 Jul 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay for our family
Lori S.
Stayed 5 nights in Jul 2025
10/10 Excellent
Michael S.
30 Jun 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Experience
Michael S.
Stayed 3 nights in Jun 2025
About the host
Hosted by Michael Perrotta
We are an active couple who is happiest when adventuring outdoors, traveling to lesser known corners of the world, hanging out with family, or snuggling with our staffy rescue. We chose DCL for its four-season fun and close proximity, so we can share The Lookout with our dearest and nearest!
Why they chose this property
We love the lake views and central location -- all activities, no matter if it’s paddling on the lake during summertime or skiing at WISP in the winter, are only within minutes! We came up with The Lookout name because it feels like you’re looking out amongst the trees. Viewing the fall leaves reflecting on the lake… OMG, such peace! Being able to walk to Brenda’s pizza (hands down the BEST pizza on the lake!), is a HUGE perk too. It’s always our first meal when we arrive.
What makes this property unique
We are nature lovers so worked hard to bring the outside in! We also prioritized comfort, hoping you’ll feel comfy-cozy and at home. Since we cater to groups, we’ve tried to think through even little touches to make your stay go smooth, like different coffee mugs so no one has to worry about whose coffee is whose!
Languages:
English
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