The Best Private
Villas in Maryland

Travel Guide | August 2025
Set your dates to see room prices:

1 The Dacha. Cumberland vacation (Cumberland)

The Dacha. Cumberland vacation The Dacha. Cumberland vacation The Dacha. Cumberland vacation 27+
images 

2 Salisbury Cottage (Salisbury)

Salisbury Cottage Salisbury Cottage Salisbury Cottage 27+
images 

3 Charming Family Home 7 mins to Beach Dog Friendly (Ocean City)

Charming Family Home 7 mins to Beach Dog Friendly Charming Family Home 7 mins to Beach Dog Friendly Charming Family Home 7 mins to Beach Dog Friendly 27+
images 

4 Patty's Place in Downtown Frederick (Frederick)

Patty's Place in Downtown Frederick Patty's Place in Downtown Frederick Patty's Place in Downtown Frederick 27+
images 

5 Logan's House in Downtown Frederick (Frederick)

Logan's House in Downtown Frederick Logan's House in Downtown Frederick Logan's House in Downtown Frederick 27+
images 

6 Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr (Oakland)

Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr Jamesons Cabin! 8 Minutes to Wisp, HotTub, FirePit, Pets, EV Chgr 27+
images 

7 Reservoir Hill Mansion - 4 bedrooms (Baltimore)

Reservoir Hill Mansion - 4 bedrooms Reservoir Hill Mansion - 4 bedrooms Reservoir Hill Mansion - 4 bedrooms 27+
images 

8 Foxes Den a Home in Ocean Pines (Ocean Pines)

Foxes Den a Home in Ocean Pines Foxes Den a Home in Ocean Pines Foxes Den a Home in Ocean Pines 27+
images 

9 Salisbury Hideaway (Salisbury)

Salisbury Hideaway Salisbury Hideaway Salisbury Hideaway 27+
images 

10 Zen Mountainside Retreat - Spa & Amazing Views! Hot tub, Fire pit & Decks (Hagerstown)

Zen Mountainside Retreat - Spa & Amazing Views! Hot tub, Fire pit & Decks Zen Mountainside Retreat - Spa & Amazing Views! Hot tub, Fire pit & Decks Zen Mountainside Retreat - Spa & Amazing Views! Hot tub, Fire pit & Decks 27+
images 

11 Small House on Gentleman’s Farm (Bel Air)

Small House on Gentleman’s Farm Small House on Gentleman’s Farm Small House on Gentleman’s Farm 27+
images 

12 Vintage Charm: Annapolis Retreat (Annapolis)

Vintage Charm: Annapolis Retreat Vintage Charm: Annapolis Retreat Vintage Charm: Annapolis Retreat 27+
images 

13 Pop Pop's Place (Ocean City)

Pop Pop's Place Pop Pop's Place Pop Pop's Place 27+
images 

14 Lock Keepers Cottage on C&O Canal/Potomac River (Sharpsburg)

Lock Keepers Cottage on C&O Canal/Potomac River Lock Keepers Cottage on C&O Canal/Potomac River Lock Keepers Cottage on C&O Canal/Potomac River 27+
images 

15 Anchors Away Abode (Annapolis)

Anchors Away Abode Anchors Away Abode Anchors Away Abode 27+
images 

16 Neptune By The Water (Annapolis)

Neptune By The Water Neptune By The Water Neptune By The Water 27+
images 

17 Annapolis Escape Steps to Harbor backs to Gate 1 (Annapolis)

Annapolis Escape Steps to Harbor backs to Gate 1 Annapolis Escape Steps to Harbor backs to Gate 1 Annapolis Escape Steps to Harbor backs to Gate 1 27+
images 

18 Weems Creek Cottage, Annapolis Waterfront (Annapolis)

Weems Creek Cottage, Annapolis Waterfront Weems Creek Cottage, Annapolis Waterfront Weems Creek Cottage, Annapolis Waterfront 27+
images 

19 Peaceful 3BR Home Near SU, Sports Fields, Civic Center, Zoo & Ocean City (Salisbury)

Peaceful 3BR Home Near SU, Sports Fields, Civic Center, Zoo & Ocean City Peaceful 3BR Home Near SU, Sports Fields, Civic Center, Zoo & Ocean City Peaceful 3BR Home Near SU, Sports Fields, Civic Center, Zoo & Ocean City 27+
images 

20 The Orange Crush - 5BR Beachfront Family Retreat (Ocean City)

The Orange Crush - 5BR Beachfront Family Retreat The Orange Crush - 5BR Beachfront Family Retreat The Orange Crush - 5BR Beachfront Family Retreat 27+
images 
Show
map
Find Private villas in:

Help out? Suggest a venue that would make this list better.

Suggest a venue