Very familiar
Hello - I am very familiar with just about every Colorado ski resort there is. The choice really depends on what you plan to do, who you plan to doit with and your budget.
Steamboat Springs - A excellent all around resort with Beginner to Mid-Advance slopes. A reasonable challenge of abilities. The resort and the community are soft on the budget and are very friendly. Many other activities outside of skiing as well and a dinner sleigh ride should be on your schedule. This is a family town that just happens to have a ski resort. Seasonal jet service is available from many cities including frequent connections through Denver.
Aspen / Snowmass - Posh, expensive, a little snooty and excellent skiing with a wide variety available. Not my cup of tea; but, budget and attitude aside, it is a fun place to at least visit. Air service can be VERY spotty with connections via DEN and limited N/S service from LAX & MSP. Plan on possible diversions to GJT & DEN throughout the winter. Suggest, flying into EGE and driving, plus you get to enjoy Glenwood Springs on the way.
Vail Valley - Which includes Vail, Arrowhead, Beaver Creek, Avon and Lionshead. ALOT of options; but, not for everyone. I tink of this as a strip mall with the exception of Beaver Creek which is superior. You will not see many people twice as most travelers will end up across a 40 mile long corridor or resorts and properties. Vail Resorts offers ski passes which can be used at many different area resorts, so if variety is a key to your decision, this may be a winner for you. Expensive and plan on waits for lots of stuff. Fly to EGE or drive from DEN.
Breackenridge - A nice town that really has grown up. Traffic Traffic Traffic; but once in town, you could exist without a car and even take a shuttle over to Keystone or Copper Mountain. Prices are reasonable as they compete for the "front range" business and there are always good deals for 7 day stays. Fly into DEN is your best choice with shuttle van service or a rental car to Breck.
Crested Butte - My personal favorite as I enjoy a remote adventure. This town is very quaint, friendly and budget concious. You could also stay in Gunnison and save alot of $$$. The hill is challenging and the resort is very family friendly. Like Steamboat Springs, there is seasonal servce as well as connection flights via Denver. This is a nice "Western" escape vacation as is Steamboat.
Telluride - This is such a fun place; but, VERY difficult to get to as compared to the other Colorado resorts. Jet service to Montrose & Grand Junction with prop service to Telluride. A nice mix of skiing from Novice to Chellenging and a truly beautiful place to be. Pricey; but, outside of the newer resorts, are within reach for most.
Winter Park - Close to Denver, family friendy and offers a variety of activities beyond skiing with tubbing, cross county, etc. The fun is also coordinating your trip along with the SkiTrain to/from Denver to Winter Park. A must do! The prices are excellent, activities expansive and skiing with Mary Jane can range from beginner to Advanced. With proximiyt to Denver, weekends can get crowded; but, just ski the bowls and you should be fine.
Eldora, Monarch, Silverton, Powderhorn, Copper; etc. Nice places; but, did not discuss them as you seem to be looking for a destination vacation. I would recommend each of these for a quick trip though.
Suggestions?
Family - Steamboat Springs
Activities - Winter Park
Variety - Vail Valley / Breckenridge
Romance - Crested Butte
Party! - Breckenridge
Budget Buster - Telluride
Skiing - Telluride / Jackson Hole!
Cost - Winter Park
I only briefly mentioned Jackson Hole under "skiing" as I stayed to Colorado resorts; but, this place is the king when it comes to challenging your abillties. Plus, it happens to be in a great town and Snow King Mountain plus nearby Idaho resorts offer a nice variety of skiing. Can be pricey to fly to; but, reasonable lodging is available once in town. Summer is FANTASTIC as well.
Good Luck!