Introduction
Maryland might seem modest in size, but when it comes to scenery, vibes, and charming vacation rentals—it punches way above its weight. Whether you’re craving a tranquil lake house where you can unzip your shoes and dip your toes in the water, a cozy cabin high in the woods with snow at your doorstep in winter, or a stylish loft in Baltimore’s lively neighborhoods—there’s something here for every mood and every budget.
If you want real places with real prices you can book in 2025, I’ve trawled the listings so you can pick rentals that match your style: from romantic retreats to large group homes, luxury hideaways to budget gems. Here are some of our top picks in Maryland to start planning your escape.
Best Lakefront Airbnbs in Deep Creek Lake & Surrounds
1. Timberlodge (Swanton) — Large Lakefront Home with Indoor Pool & Dock
- Price: approx. $3,624/night (for a large group; this is a very premium option)
- Details: 9 bedrooms, 8 bathrooms. Sleeps large groups (families, group trips). Indoor pool, hot tub, full kitchen, arcade/game room, and private dock. Outdoor grills too.
- Why Stay Here: If you want to splurge for comfort, space, and every amenity, this is the kind of place where you check in and don’t want to leave. Great for big celebrations, family reunions, or group retreats.
2. Snow Escape — Log Cabin at Wisp Resort
- Price: ~ $1,407/night
- Details: 6 bedrooms, 4 baths. Sleeps up to ~16 people. Game room (ping-pong, etc.), two fireplaces, hot tub. Very close to Wisp Resort and Deep Creek Lake.
- Why Stay Here: Perfect for large friend or family groups who want access to adventure (skiing, hiking) and lots of space. There’s rustic charm coupled with luxury touches.
3. Dog Friendly Lakefront Retreat w/ Pool & Hot Tub — Oakland Area
- Price: approx. $3,357/night for a high-capacity, high-amenity home.
- Details: 7 bedrooms, indoor pool & spa, 5,810 sq ft. Hosts gym, multiple BBQs. Great mix of relaxation + functionality. Pet friendly.
- Why Stay Here: If bringing pets, large family, or groups that love both rest & activity, this spot gives luxury, space, and lake access.
4. Lakeslee Lodge — Lake Access Family Rental
- Price: ~$868/night for a 6-bedroom, sleeps ~16 people home.
- Details: Private dock, lake views, large kitchen, outdoor areas. Great for multi-generation family vacations or large groups.
- Why Stay Here: More affordable per person for big groups, with lake access. If you want crowd capacity without completely blowing your budget, this is a smart pick.
5. Dog-Friendly Hot Tub Cabin — Small Group Option
- Price: ~$246/night for 2 bedrooms, 2 baths (sleeps ~8).
- Details: Woodsy cabin near Deep Creek Lake, with hot tub, fireplace, firepit. Secluded setting but close enough to attractions. Pet friendly.
- Why Stay Here: Ideal for couples or small groups who want charm, privacy, and a cozy spot with character. Great for long weekends.
Baltimore & City/Staying Out Options Near Maryland
6. Average Daily Rate & Example in Baltimore
- General Rate: The average Airbnb daily rate in Baltimore for entire homes is about $153/day according to recent vacation rental data.
- Sample Stay: “Baltimore Studio, Indoor Parking” ~ $138/night for a 1-bedroom apartment in Baltimore. Close to amenities, good for guests who want value without compromising location.
What These Listings Tell Us (Mini Review Notes)
- Value vs Luxury: The Deep Creek Lake region listings show a wide range—from ultra-luxurious multi-bedroom massive homes pulling in high prices per night, to more modest cabins that are still very charming and much more affordable for smaller groups.
- Group Travel: If you’re traveling with many people, the “per person cost” can become very reasonable in the big homes. Splitting ~$3,000/night among 12–16 people becomes quite decent.
- Amenities Matter: The homes with docks, hot tubs, game rooms, pet-friendly policies, and easy access to nature tend to be the ones with high ratings and higher price tags. If you only need basic comforts, you can save by picking simpler cabins.
- Seasonal Price Variation: Deep Creek Lake is especially busy in summer (lake season) and winter (ski/hiking). Prices shoot up in peak months, so booking ahead helps.
Coastal, Unique & Luxury, City-and Group-Friendly Airbnbs in Maryland
8. Spacious Renovated Pet-Friendly Home with Game Room — Ocean City, Maryland
- Price: About $2,855/night for ~5 bedrooms + additional sleeping options.
- Details: Sleeps ~14, pet-friendly, includes a game room (billiards, air hockey etc.), balcony with canal views, very close to the beach and boardwalk.
- Why Stay Here: If you’re travelling in a large group—extended families or friends—this is a fun coastal stay. You get both action (boardwalk, beach) and indoor entertainment, which is great if weather turns. The pet-friendly angle is big if you don’t want to leave Fido behind.
9. Modern Farmhouse — Reisterstown, Maryland
- Price: ~$825/night via Airbnb; Vrbo listing shows approx $585/night during less busy times.
- Details: Entire home, 5 bedrooms, 4.5 bathrooms. Sleeps ~14. Has spacious indoor & outdoor entertaining areas including a pool table, screened deck, large backyard, gardens.
- Why Stay Here: If you want luxury + space without being right on the beach, this kind of place offers a lot. The farmhouse style gives character; good for large families or groups wanting quiet luxury and privacy. It’s far enough to enjoy nature and calm, close enough to amenities.
10. Treehouse Rentals Around Maryland
Here are a few standout treehouse-style stays:
- South River View Treehouse — Riva, Maryland
- Price: from $125+/night for 1 bedroom + deck + basic amenities.
- Features: Deck with river views, forested surroundings, small but cozy, good for couples or a small group of up to ~4.
- Price: from $125+/night for 1 bedroom + deck + basic amenities.
- Antietam Creek Treehouse — Keedysville, Maryland
- Price: approx $183+/night for 2 bedrooms.
- Features: Secluded, rustic yet comfortable; ideal if you want nature, quiet, and perhaps exploring nearby historical sites like Antietam.
- Price: approx $183+/night for 2 bedrooms.
- The Eagle’s Nest Treehouse — Deep Creek Lake Area
- Price: from $295+/night for up to ~5 people.
- Features: Elevated wooden structure, rustic/cabin-treehouse blend, nice decor, outdoor space, fire pit, etc.
- Price: from $295+/night for up to ~5 people.
- Custom Built Treehouse — Nottingham, MD
- Why Treehouses? These stays are great for couples, small groups, or anyone wanting a different kind of getaway—something Instagrammable, quiet, and closer to nature. If you don’t need full luxury, the lower-price ones are very good value.
11. Ocean City Condos & Beachfront Houses
Many condos and homes in Ocean City offer value and location:
- Ocean City Houses / Homes & Waterfront Condos
- Starting Prices: Some home rentals start around $40/night before fees & taxes for lower-end small houses or condos. More premium beachfront or larger homes are much more.
- Example Stays: There are many condos “Ocean Block” or near the boardwalk, 2-bedroom / 2-bath units, or homes with private parking, pools, or ocean views.
- Starting Prices: Some home rentals start around $40/night before fees & taxes for lower-end small houses or condos. More premium beachfront or larger homes are much more.
- Why Stay Here: For beach lovers, proximity matters. Even a short walk to the beach makes a big difference. Condos with pools and ocean views cost more, but if you find off-peak deals, they can be gems. Also good for families.
12. Large Group / Family-Friendly Rentals Near the Bay & Outside the City
- “Airy & Spacious Modern Farmhouse” – Reisterstown (covered above) is a good example.
- Other homes near Annapolis / Baltimore outskirts tend to offer large space, multiple bedrooms, and amenities like grill/backyard, sometimes water access near the Chesapeake Bay
Romantic Escapes, Budget Stays, and Final Picks
13. Romantic Cabin with Hot Tub — Oakland, Maryland
- Price: from $240/night
- Details: 2 bedrooms, 2 baths, a private hot tub, wood-burning fireplace, and a wraparound deck. Perfect for couples or small families wanting a cozy retreat.
- Why Stay Here: Tucked in the woods yet close to Deep Creek Lake, this rental is ideal for a peaceful, romantic getaway with all the essentials for a relaxing weekend.
14. Secluded Cottage on Chesapeake Bay
- Price: around $180/night
- Details: 1 bedroom, 1 bathroom, direct bay views, private deck, and kayak access.
- Why Stay Here: A dreamy hideaway for two, this cottage is all about sunsets, stargazing, and slow mornings with coffee on the deck.
15. Historic Townhouse in Annapolis
- Price: about $320/night
- Details: 3 bedrooms, 2 baths, historic charm with modern updates, walking distance to downtown shops and the harbor.
- Why Stay Here: For travelers who love city stays with character, this townhouse is the perfect blend of history, culture, and convenience.
16. Designer Loft in Downtown Baltimore
- Price: starting at $150/night
- Details: 1 bedroom, open-plan living, industrial-chic design, rooftop access.
- Why Stay Here: A stylish base for exploring Baltimore’s Inner Harbor, museums, and nightlife. Great for solo travelers or couples who love urban energy.
17. Chesapeake Bayfront Mansion for Large Groups
- Price: approx $1,200/night
- Details: 7 bedrooms, 6 bathrooms, private pier, swimming pool, gourmet kitchen, and expansive outdoor spaces.
- Why Stay Here: Perfect for weddings, reunions, or group vacations, this mansion combines elegance with breathtaking water views.
18. Tiny House Retreat in Frederick
- Price: from $115/night
- Details: Compact design with loft bedroom, kitchenette, and outdoor firepit.
- Why Stay Here: A budget-friendly yet stylish option, tiny houses are fun, cozy, and eco-friendly. Perfect for couples who want something unique without breaking the bank.
19. Farm Stay on a Working Maryland Ranch
- Price: about $140/night
- Details: 2 bedrooms in a renovated barn, outdoor seating, and plenty of opportunities to see horses, goats, and farm life.
- Why Stay Here: This rustic farm experience is great for families with kids or anyone curious about rural Maryland charm.
20. Ocean City Condo with Pool Access
- Price: around $190/night
- Details: 2 bedrooms, 2 baths, pool access, ocean block location.
- Why Stay Here: For those who want convenience and affordability, this condo offers everything you need for a classic Ocean City beach trip.
21. Kid-Friendly Cabin Near Cunningham Falls State Park
- Price: from $220/night
- Details: 3 bedrooms, stocked game room, outdoor fire pit, and access to hiking trails.
- Why Stay Here: Families love this cabin for its balance of nature, space for kids to play, and easy access to one of Maryland’s most beautiful state parks.
22. Couples’ Cottage with Fireplace — Near Hagerstown
- Price: about $175/night
- Details: 1 bedroom, wood-burning fireplace, private deck, and close to wineries.
- Why Stay Here: A romantic base for wine lovers and couples wanting to escape city life for a weekend.
23. The Ultimate Maryland Airbnb — Luxury Lakefront Lodge
- Price: around $850/night
- Details: 5 bedrooms, hot tub, private dock, gourmet kitchen, game room, and panoramic lake views.
- Why Stay Here: If you want one Maryland Airbnb that has it all—scenery, luxury, space, and comfort—this lakefront lodge is the perfect choice. It’s equally suited to families, groups of friends, or anyone who wants a dream vacation in the state’s most beloved destination.
Conclusion
Maryland’s Airbnbs are as diverse as the state itself. From romantic cottages for two to sprawling mansions for twenty, from treehouses in the woods to modern lofts in the city, there’s something here for every traveler, every season, and every budget. Whether your perfect getaway involves kayaking on Deep Creek Lake, sipping wine by the Chesapeake Bay, or strolling through Annapolis’s historic streets, your ideal stay is just a booking away.